Editing Sideshow Bob

{{short description|Fictional character from The Simpsons franchise}}
{{Use American English|date=May 2025}}
{{Use mdy dates|date=July 2018}}
{{Infobox character
| name = Sideshow Bob
| series = [[The Simpsons]]
| image = File:C-bob.png
| first = "[[The Telltale Head]]" (1990)
| creator = [[Al Jean]]<br />[[Mike Reiss]]<br />[[Sam Simon]]<br />[[Matt Groening]]<br />[[Jay Kogen]]<br />[[Wallace Wolodarsky]]<br />[[Brad Bird]]
| designer = Matt Groening
| voice = [[Kelsey Grammer]]
| full_name = Robert Underdunk Terwilliger Jr.{{Efn|name="Middle Name"}}
| gender = Male
| occupation = Television personality<br />Former Mayor of Springfield<br />Former Mayor of Salsiccia<br />Scientist<br />Professor<br />Actor<br />Criminal<br />
| family = Dr. Robert Terwilliger Sr. (father)<br />Dame Judith Onderdonk (mother)<br />Cecil Terwilliger (brother)
| children = Gino (son)
| spouse = [[Patty and Selma#Selma Bouvier|Selma Bouvier]] (ex-wife)<br />Francesca (ex-wife)<br />Tasha (wife)
| relatives = [[Patty and Selma#Patty Bouvier|Patty Bouvier]] (ex-sister-in-law)<br />[[Marge Simpson]] (ex-sister-in-law)<br />[[Homer Simpson]] (ex-brother-in-law)<br />[[Bart Simpson]] (ex-nephew)<br />[[Lisa Simpson]] (ex-niece)<br />[[Maggie Simpson]] (ex-niece)
}}

'''Robert Underdunk "Bob" Terwilliger Jr.''', [[Doctor of Philosophy|PhD]],{{Efn|name="Middle Name"|According to one of the show's writers, [[Bill Oakley]], Sideshow Bob's middle name is Onderdonk,<ref name="Onderdonk">{{Cite twitter |title=Yes @Jeopardy you made a rare mistake. It's "Onderdonk". And @Joshstrangehill and I are certain cause we wrote that script. Cc: @KenJennings |date=March 13, 2024 |author=Oakley, Bill |user=thatbilloakley |number=1768113342210867416}}</ref> after [[Henry Onderdonk]].<ref>{{Cite twitter |title=This is where we got the name, it was from a hymnal we saw in high school - |date=March 13, 2024 |author=Oakley, Bill |user=thatbilloakley |number=1768349814104953218}}</ref> However, in all other references, including books by Simpsons' creator Matt Groening,{{Sfn|Groening|2010|pp=207, 1183, 1193}} and [[subtitles]] of the show,<ref>{{cite episode |title=Sideshow Bob Roberts |episode-link=Sideshow Bob Roberts |series=The Simpsons |series-link=The Simpsons |network=Fox |airdate=1994-10-09 |season=6 |number=5 |time=6:27}}</ref> it is Underdunk.}}<ref>{{Cite episode |title=The Man Who Grew Too Much |episode-link=The Man Who Grew Too Much |series=The Simpsons |series-link=The Simpsons |season=25 |number=12 |time=7:20 |quote=Dr. Sideshow Bob. [...] PhD.}}</ref> better known as '''Sideshow Bob''', is a recurring antagonist in the animated television series ''[[The Simpsons]]''. He is voiced by [[Kelsey Grammer]] and first appeared in the episode "[[The Telltale Head]]". Bob is a self-proclaimed genius who is a graduate of [[Yale University]] and a champion of [[high culture]], including the adoption of a [[Northeastern elite accent|transatlantic accent]], similar to that of Grammer's portrayal of [[Frasier Crane|Dr. Frasier Crane]] from the sitcoms ''[[Cheers]]'' and ''[[Frasier]]''. He began his career as a sidekick on [[Krusty the Clown]]'s television show, but after enduring constant abuse, Bob framed his employer for armed robbery in "[[Krusty Gets Busted]]", only to be foiled by [[Bart Simpson]], and sent to prison. Bob started seeking revenge against Bart while in prison, and the two became feuding archenemies.

Bob made his second major appearance in [[The Simpsons (season 3)|season three]]'s "[[Black Widower]]"; the writers echoed the premise of [[Wile E. Coyote and the Road Runner|Wile E. Coyote chasing the Road Runner]] by having Bob unexpectedly insert himself into Bart's life, threatening to disrupt and end it through murder. Starting with that appearance and thereafter, Bob has assumed the role on ''The Simpsons'' of an [[villain|evil genius]]. Episodes in which he is a central character typically involve Sideshow Bob being released from prison and executing an elaborate revenge plan, usually foiled by Bart and [[Lisa Simpson|Lisa]]. His plans often involve death and destruction, usually targeted at Bart or, less often, Krusty, though he [[The Italian Bob|starts targeting]] the entire Simpson family in [[The Simpsons (season 17)|season 17]]. In [[The Simpsons (season 27)|season 27]], however, during the first segment of "[[Treehouse of Horror XXVI]]", entitled "Wanted: Dead, Then Alive", Bob finally gets his wish of killing Bart, commenting that he spent 24 years trying to kill a ten-year-old child; however, he becomes bored with Bart dead, so he brings him back to life so that he can repeatedly kill Bart over and over again.<ref>{{cite magazine |last=Hibberd |first=James |date=June 6, 2015 |url=http://www.ew.com/article/2015/06/06/simpsons-sideshow-bob-kill-bart |title=The Simpsons scoop: Sideshow Bob to finally kill Bart this fall |magazine=[[Entertainment Weekly]] |access-date=June 11, 2015}}</ref><ref>{{cite web |last=Nicholson |first=Max |date=July 11, 2015 |url=http://www.ign.com/articles/2015/07/11/comic-con-2015-the-simpsons-panel-teases-new-treehouse-of-horror |title=Comic-Con 2015: The Simpsons Panel Teases New "Treehouse of Horror" |website=[[IGN]] |access-date=September 18, 2015}}</ref><ref>{{cite magazine |last=Snierson |first=Dan |date=October 8, 2015 |url=http://www.ew.com/article/2015/10/08/simpsons-treehouse-horror-sideshow-bob-ren-stimpy |title=Simpsons' 'Treehouse of Horror XXVI': First Look and details on Sideshow Bob killing Bart and more |magazine=Entertainment Weekly |access-date=October 11, 2015}}</ref>

Despite his villainous deeds, Sideshow Bob shares some personality traits of Grammer character Frasier Crane, and he has been described as "Frasier pickled in arsenic".<ref name="Arsenic"/> Several parallels have been explicitly drawn in ''The Simpsons'' between Bob and Frasier Crane—Bob's brother Cecil and his father were played by [[David Hyde Pierce]] and [[John Mahoney]], respectively, echoing the roles they played in ''Frasier''. Grammer, who based Bob's voice on that of actor [[Ellis Rabb]], has been praised for his portrayals of the character. In 2006, he won an Emmy for [[Primetime Emmy Award for Outstanding Voice-Over Performance|Outstanding Voice-Over Performance]] for his work in the episode "The Italian Bob".

As of season 36, Sideshow Bob has appeared in more than 40 episodes, had speaking appearances in 25 of these, and been featured as the main character in 15. The most recent of the latter, "[[The Yellow Lotus]]", aired during [[The Simpsons (season 36)|the 36th season]], and his most recent speaking appearance was in "[[Treehouse of Horror XXXIV]]" in [[The Simpsons (season 35)|the 35th season]].<ref>{{cite tweet |last=Price |first=Michael |user=mikepriceinla |number=1581713481124188160 
|date=October 16, 2022 |title=@WonderedAlways Yes but I can't tell you when or what! |language=en |access-date=July 19, 2023 |archive-url=https://web.archive.org/web/20211210000508/https://twitter.com/mikepriceinla/status/1581713481124188160?s=46&t=bT2rLJXzlvagbrScuLpMdQ |archive-date=December 10, 2021 |url-status=live}}</ref> In addition to his recurring role in the series, Sideshow Bob has made several appearances in other ''Simpsons'' media and is mentioned in several more episodes. He appears in the [[List of The Simpsons comics#Simpsons Comics|''Simpsons Comics'']], the 2007 video game ''[[The Simpsons Game]]'', and stars as the main antagonist in [[The Simpsons Ride|''The Simpsons'' Ride]] at Universal Studios' theme parks. A lover of [[Gilbert and Sullivan]] [[operetta]]s, Sideshow Bob is also known for his singing voice; several of Grammer's performances have been included in [[The Simpsons discography|''The Simpsons'' musical compilations]].

==Appearances==

===On ''The Simpsons''===
The character of Sideshow Bob began his career as the non-speaking sidekick who would only use a 
whistle 
on [[Krusty the Clown]]'s television show.<ref>{{cite episode |title=The Telltale Head |episode-link=The Telltale Head |series=The Simpsons |credits=[[Al Jean|Jean, Al]]; [[Mike Reiss|Reiss, Mike]]; [[Matt Groening|Groening, Matt]]; [[Sam Simon|Simon, Sam]]; [[Rich Moore|Moore, Rich]] |network=Fox |airdate=1990-02-25 |season=1 |number=8}}</ref> Bob first appears in "[[The Telltale Head]]" ([[The Simpsons (season 1)|season 1]], 1990). In the episode, he and Krusty plan a big event for whoever knows information of who captured the head of Jebediah Springfield's statue, and joins in on the town mob when it is  discovered that [[Bart Simpson]] took it. However, after repeated instances of abuse, including being [[Human cannonball|shot from a cannon]] and [[Pieing|hit constantly with pies]], the [[Yale University|Yale]]-educated Bob became angry with Krusty and resentful of the clown's success.

In "[[Krusty Gets Busted]]" ([[The Simpsons (season 1)|season 1]], 1990), Bob disguised himself as Krusty and framed him for armed robbery of the [[Kwik-E-Mart]]. After Krusty is arrested, Bob takes control of the show, introducing children to elements of [[high culture]]. However, Bob's reign is short-lived; Bart exposes him as the robber, Krusty is released, and Bob is fired and sent to jail.<ref>{{cite episode |title=Krusty Gets Busted |episode-link=Krusty Gets Busted |series=The Simpsons |credits=[[Jay Kogen|Kogen, Jay]]; [[Wallace Wolodarsky|Wolodarsky, Wallace]]; [[Brad Bird|Bird, Brad]] |network=Fox |airdate=1990-04-29 |season=1 |number=12}}</ref>

In "[[Black Widower]]" ([[The Simpsons (season 3)|season 3]], 1992), Bob's first major appearance after framing Krusty, he is released from prison and marries Bart's aunt [[Patty and Selma Bouvier|Selma Bouvier]] as part of a scheme to [[Inheritance|inherit]] money she has [[Investment|invested]] in the [[stock market]]. Bob attempts to blow Selma up during their [[honeymoon]], but Bart again foils the plan and Sideshow Bob returns to prison.<ref name="Black Widower">{{cite episode |title=Black Widower |episode-link=Black Widower |series=The Simpsons |credits=[[Jon Vitti|Vitti, Jon]]; [[David Silverman (animator)|Silverman, David]] |network=Fox |airdate=1992-04-09 |season=3 |number=56}}</ref>

After being [[parole]]d from prison in "[[Cape Feare]]" ([[The Simpsons (season 5)|season 5]], 1993), Bob targets Bart directly, threatening him repeatedly and forcing the Simpsons into hiding as part of the [[United States Federal Witness Protection Program|Witness Relocation Program]]. Bob follows them to their hideout, a [[houseboat]] on Terror Lake, and, after subduing the family, prepares to kill Bart. He allows a final request, however, and Bart asks to hear Bob sing the entire score of ''[[H.M.S. Pinafore]]''. Although Bob finishes singing and nearly kills Bart, the delaying tactic leads to Bob's third arrest as the houseboat had drifted all the way back to Springfield.<ref name="Feare">{{cite episode |title=Cape Feare |episode-link=Cape Feare |series=The Simpsons |credits=Vitti, Jon; Moore, Rich |network=Fox |airdate=1993-10-07 |season=5 |number=83}}</ref>

Bob is released from prison once again in "[[Sideshow Bob Roberts]]" ([[The Simpsons (season 6)|season 6]], 1994), and runs for Mayor of [[Springfield (The Simpsons)|Springfield]] as the [[Republican Party (United States)|Republican Party]] candidate. He defeats [[Democratic Party (United States)|Democratic Party]] incumbent [[Joe Quimby]] in a landslide, but Bart and Lisa discover from [[Waylon Smithers]]  that Bob [[Electoral fraud|rigged the election]] by using the names of deceased people. Bob is put on trial and claims himself innocent, but is tricked by Bart and Lisa to expose himself guilty, leading to another incarceration.<ref name="Roberts">{{cite episode |title=Sideshow Bob Roberts |episode-link=Sideshow Bob Roberts |series=The Simpsons |credits=[[Bill Oakley|Oakley, Bill]]; [[Josh Weinstein|Weinstein, Josh]]; [[Mark Kirkland|Kirkland, Mark]] |network=Fox |airdate=1994-10-09 |season=6 |number=108}}</ref>

Sideshow Bob escapes from prison for the first time in "[[Sideshow Bob's Last Gleaming]]" ([[The Simpsons (season 7)|season 7]], 1995), and threatens to blow up Springfield with a [[nuclear bomb]] unless the city stops broadcasting all television shows. He is thwarted when he finds out that the bomb itself is a dud, then kidnaps Bart and flies the [[Wright Flyer|Wright Brothers' plane]] in an attempt to kill himself, Bart, and Krusty (who is hiding inside a shack, improvising a performance on the [[Emergency Broadcast System]]). This too is thwarted, and Bob returns to prison.<ref>{{cite episode |title=Sideshow Bob's Last Gleaming |episode-link=Sideshow Bob's Last Gleaming |series=The Simpsons |credits=[[Spike Feresten|Feresten, Spike]]; [[Dominic Polcino|Polcino, Dominic]] |network=Fox |airdate=1995-10-26 |season=7 |number=137}}</ref>

In the [[The Simpsons (season 8)|following season]], Bob takes advantage of the prison's [[Work release|work release program]], and appears to be genuinely redeemed. "[[Brother from Another Series]]" ([[The Simpsons (season 8)|season 8]], 1997) reveals that Bob only became Krusty's sidekick after his younger brother [[List of recurring The Simpsons characters#Cecil Terwilliger|Cecil]] failed an audition ten years prior, because Krusty considered Bob to be a perfect [[comic foil]].<ref name=bfas>{{cite episode |title=Brother from Another Series |episode-link=Brother from Another Series |series=The Simpsons |credits=[[Ken Keeler|Keeler, Ken]]; [[Pete Michels|Michels, Pete]] |network=Fox |airdate=1997-02-23 |season=8 |number=169}}</ref> [[Timothy Lovejoy|Reverend Lovejoy]] declares him a changed man and recommends him for a [[work release]] opportunity. Bob is discharged from prison into the care of Cecil, who is now [[Springfield (The Simpsons)|Springfield]]'s chief [[Hydraulic engineering|hydrological and hydrodynamical engineer]]. However, the scheming Cecil, still smarting over his failed audition for Krusty, tries to frame Bob by [[Sabotage|sabotaging]] the Springfield Dam by having it burst across Springfield. Bob, Bart, and Lisa together stop Cecil and save the town, and both brothers, despite Bob's genuine innocence, are sent to prison.<ref name=bfas/>

Bob returned in "[[Day of the Jackanapes]]" ([[The Simpsons (season 12)|season 12]], 2001), where he discovers in prison that Krusty has erased all of the early shows featuring Sideshow Bob as Krusty himself is declaring his fifth and final retirement after being annoyed with the [[Television producer|network executives]]. Bob is released from prison and develops a plot to kill Krusty using Bart as a [[Suicide attack|suicide bomber]] during Krusty's retirement special. Everything goes just as Bob had planned, and just when Bob was about to succeed in murdering both his enemies, he overhears Krusty publicly holding himself responsible for turning Bob into a criminal, expressing his regret of mistreating Bob during his years as Sideshow. To appease things, Krusty sings himself a song on Bob's behalf, and being touched by this, Bob decides to abort his plan of [[attempted murder]] and reconciles with Krusty, although he is returned to prison for it.<ref>{{cite episode |title=Day of the Jackanapes |episode-link=Day of the Jackanapes |series=The Simpsons |credits=Jean, Al; [[Michael Marcantel|Marcantel, Michael]] |network=Fox |airdate=2001-02-18 |season=11 |number=261}}</ref>

Bob's aid is sought by Springfield police in "[[The Great Louse Detective]]" ([[The Simpsons (season 14)|season 14]], 2002). After an attempt is made on [[Homer Simpson]]'s life, Bob is released from prison to help find the culprit. During the adventure, Bob is given advice to kill Bart without hesitation, instead of being tricked into delay or screwing up on his plots. When the mystery is solved (it was [[Frank Grimes (The Simpsons)|Frank Grimes]]'s son), he returns to murder Bart. However, Bob finds he is "accustomed to his [Bart's] face" and cannot do it.<ref>{{cite episode |title=The Great Louse Detective |episode-link=The Great Louse Detective |series=The Simpsons |credits=[[John Frink|Frink, John]]; [[Don Payne (writer)|Payne, Don]]; [[Steven Dean Moore|Moore, Steven Dean]] |network=Fox |airdate=2002-12-15 |season=14 |number=297}}</ref>

In "[[The Italian Bob]]" ([[The Simpsons (season 17)|season 17]], 2005), it is revealed that Bob had moved to [[Italy]] to make a fresh start. He was eventually elected mayor of the village of Salsiccia in [[Tuscany]] and marries a local woman named [[List of recurring The Simpsons characters#Francesca Terwilliger|Francesca]], with whom he has a son named [[List of recurring The Simpsons characters#Gino Terwilliger|Gino]]. The Simpson family, in Italy to retrieve a car for [[Montgomery Burns|Mr. Burns]], encounters him by chance. Bob welcomes them with hospitality on the condition that they not reveal his dark felonious past; however, a drunken Lisa jokes about Bob's criminal deeds and reveals his prison uniform, alienating Bob from his citizens. Bob is angered enough to change his dream of killing Bart to killing the whole Simpson family. Upon catching up to Bob, his wife and his son swear a [[Feud|vendetta]] with him on all the Simpsons.<ref name="TIB">{{cite episode |title=The Italian Bob |episode-link=The Italian Bob |series=The Simpsons |credits=Frink, John; Kirkland, Mark |network=Fox |airdate=2005-12-11 |season=17 |number=364}}</ref>

The entire Terwilliger family returns in "[[Funeral for a Fiend]]" ([[The Simpsons (season 19)|season 19]], 2007) in which Bob's father, Robert Terwilliger Sr., and mother, Dame Judith Onderdonk, make their first appearances. [[List of recurring The Simpsons characters#Cecil Terwilliger|Cecil]] also appears a second time on the show. Bob at first attempts to kill the whole family a second time, but his plan fails. Bob fakes his own death during his trial and locks Bart in the [[coffin]], which he attempts to [[Cremation|cremate]] at the otherwise empty [[funeral home]] as all the Terwilligers laugh maniacally. They are foiled by Lisa and the rest of the Simpson family and sent to prison.<ref name="FFAF">{{cite episode |title=Funeral for a Fiend |episode-link=Funeral for a Fiend |series=The Simpsons |credits=[[Michael Price (writer)|Price, Michael]]; Oliver, Rob |network=Fox |airdate=2007-11-25 |season=19 |number=408}}</ref>

In "[[Sex, Pies and Idiot Scrapes]]" ([[The Simpsons (season 20)|season 20]], 2008), Bob is one of the wanted criminals in Homer and [[Ned Flanders]]'s bounty hunter job despite already being in prison, which he escapes from at the end of the episode. In "[[Wedding for Disaster]]" ([[The Simpsons (season 20)|season 20]], 2009), Bart and Lisa initially suspect Bob of kidnapping Homer to prevent him from attending his [[second wedding]] with [[Marge Simpson|Marge]] (due to a keychain they found had an 'S' and a 'B'), but Krusty provides him with an alibi, explaining to the kids that Bob was with him the whole day. Eventually, Bob and the kids discover the true culprits, [[Patty and Selma]].<ref>{{Cite web|url=http://www.foxflash.com/div.php/main/page?aID=1z4&mo=3&d=22 |title=Primetime Listings (March 21&nbsp;– March 28) |access-date=March 7, 2009 |date=March 6, 2009 |publisher=FoxFlash |url-status=dead |archive-url=https://web.archive.org/web/20090313015253/http://www.foxflash.com/div.php/main/page?aID=1z4&mo=3&d=22 |archive-date=March 13, 2009 }}</ref>
Bob also appears in “[[Coming to Homerica]]”, the 21st episode of Season 20, in a joke where the Simpson family enters the Cheers bar dressed as the Cheers cast when Sideshow Bob comes in dressed as [[Frasier Crane]].

In "[[O Brother, Where Bart Thou?]]" ([[The Simpsons (season 21)|season 21]], 2009), Bob makes a non-speaking cameo appearance in Bart's dream sequence while the latter becomes desperate of having a younger brother. [[List of recurring The Simpsons characters#Cecil Terwilliger|Cecil]] makes his third appearance in ''The Simpsons'' by appearing alongside Bob; the brothers are flying kites together. Bob reappears again in the episode "[[The Bob Next Door]]" ([[The Simpsons (season 21)|season 21]], 2010). He switches faces with his prison cellmate Walt Warren. Bob returns to Springfield and moves into the house next to the Simpson family, assuming Walt's identity. He exploits this to make his latest attempt to kill Bart legally over state lines, but is foiled again and gets taken away by [[State police (United States)|state police]].<ref name="TBND">{{cite episode |title=The Bob Next Door |episode-link=The Bob Next Door |series=The Simpsons |credits=Frink, John; [[Nancy Kruse|Kruse, Nancy]] |network=Fox |airdate=2010-05-16 |season=21 |number=463}}</ref>

Bob appears in "[[At Long Last Leave]]" ([[The Simpsons (season 23)|season 23]], 2012), the 500th episode of ''The Simpsons''. He attends a [[town meeting]] to decide if the Simpson family should be [[Exile|banished]] from Springfield, and is one of many who express their desire for it to happen.<ref name="ALLL">{{cite episode |title=At Long Last Leave |episode-link=At Long Last Leave |series=The Simpsons |credits=Price, Michael; Nastuk, Matthew |network=Fox |airdate=2012-02-19 |season=23 |number=500}}</ref> He makes a silent appearance in "[[Moonshine River]]" ([[The Simpsons (season 24)|season 24]], 2012), where he runs across the train tracks trying to kill Bart, but ends up getting hit by a train.

In "[[The Man Who Grew Too Much]]" ([[The Simpsons (season 25)|season 25]], 2014), he was revealed to be a Chief Scientist for a [[genetic engineering]] company named [[Monsanto|Monsarno]], having received the position after he was selected as a [[Human subject research|test subject]] and published the results of the experiments to which he was subjected. He and Lisa bond over their interest in [[Walt Whitman]], but Bob reveals that he has also genetically modified himself to give himself various [[superhuman]] abilities, intending to acquire [[DNA]] from the relics of various [[historical figure]]s stored in the Springfield Museum to make himself a superhuman [[dictator]]. After tempted into a murderous rage, he chases down Bart and Lisa and is about to kill them but however, he is provoked into a fight and he realizes that he has become a crude monster and jumps off the Springfield Dam. The episode ends with Bob underwater in the lake, shown to have survived because the [[gill]]s he gave himself allow him to live.

Bob also appears in "[[Clown in the Dumps]]" ([[The Simpsons (season 26)|season 26]], 2014). Having returned to prison, he offered his condolences to Krusty after the death of his father, [[Rabbi Krustofsky]]. Several episodes later, Bob returned in "[[Blazed and Confused]]" ([[The Simpsons (season 26)|season 26]], 2014), where he meets Mr. Lassen, Bart's former teacher, who was now reduced to working in prison as a [[Prison officer|guard]] after Bart's earlier actions at a "Blazing Guy" festival got him fired. Despite Lassen's offer to get him out, Bob rejects the idea that they team up as Lassen thought that they would take turns gutting Bart.

In "[[Treehouse of Horror XXVI]]" ([[The Simpsons (season 27)|season 27]], 2015), in the first segment called "Wanted: Dead, then Alive", Bob uses [[Milhouse Van Houten|Milhouse]]'s phone to trap Bart in the band classroom and successfully kills him. In peace with himself, Bob moves on from Bart to pursue other dreams, however, due to Bob chasing down Bart for so long, Bob finds his life so meaningless in Bart's absence that he creates a machine to bring Bart back to life so that he can keep killing his enemy over and over, until the other Simpsons find Bob's location and rescue Bart,  and Bart uses the resurrection machine to turn Bob into a twisted amalgamation of creatures. Bob also appears in the episode "[[Gal of Constant Sorrow]]" ([[The Simpsons (season 17)|season 27]], 2016), grunting in annoyance as he wipes off Bart's [[graffiti]] from Hettie Mae Boggs' promo poster on the wall along with [[Snake Jailbird]] and other inmates.

Bob returns in "[[Treehouse of Horror XXVII]]" ([[The Simpsons (season 28)|season 28]], 2016), the 600th episode of ''The Simpsons''. In the opening sequence, he is the self-appointed leader of a four-member group consisting of Homer's enemies, including Bob himself and the ghost of Frank Grimes. Wanting revenge once more, the group attempts to kill the Simpsons but is ultimately killed by [[Maggie Simpson|Maggie]], except Grimes's ghost. In the ending sequence, Bob is one of the characters featured in the "600" song played by [[Judith Owen]]. In "[[Havana Wild Weekend]]" ([[The Simpsons (season 28)|season 28]], 2016), Sideshow Bob appeared in the backgrounds at the Cuba's check-in.

Bob also makes a non-speaking cameo appearance in "[[The Nightmare After Krustmas]]" ([[The Simpsons (season 28)|season 28]], 2016); he is amongst the crowd witnessing Krusty nearly drowning in a frozen lake while holding up a sign saying "Die Clown". He's had a major appearance in "[[Gone Boy]]" ([[The Simpsons (season 29)|season 29]], 2017), when he tries to track down the whereabouts of Bart after he goes missing and is presumed dead. Bob finds Bart and proceeds to kill him and [[Milhouse Van Houten|Milhouse]], but saves them at the last minute due to the influence of the prison therapist's lessons of potentially moving on from wanting to kill Bart. The epilogue features an older Bob, now known as Elder Bob, being a lighthouse keeper and still having regrets of not killing Bart.

In "[[The Fat Blue Line]]" ([[The Simpsons (season 31)|season 31]], 2019), Bob escapes from prison once again, only to be hit by a rake truck. Several episodes later, in "[[Bobby, It's Cold Outside]]" ([[The Simpsons (season 31)|season 31]], 2019), he is hired to play Santa Claus at a theme park, and later helps the Simpsons discover who is stealing everyone's Christmas gifts. Bob returned in a non-speaking cameo in "[[Meat Is Murder (The Simpsons)|Meat Is Murder]]" ([[The Simpsons (season 33)|season 33]], 2022), where he is seen signing the chests of citizens like Milhouse's father [[Kirk Van Houten]] at the celebration of [[Krusty the Clown|Krusty Burger]]'s 50th anniversary, a callback to the "Die Bart, Die" scene from "Cape Feare".

In the "[[Treehouse of Horror XXXIV]]" segment "Ei8ht" ([[The Simpsons (season 35)|season 35]], 2023), in an alternative ending to "Cape Feare", Bob realizes that Bart is stalling his death by making him sing ''Pinafore'', and as a result, kills him, traumatizing Lisa. 30 years later, the Springfield Police asks Professor Lisa Simpson to look into a series of murders committed by an unknown serial killer. Perplexed, Lisa seeks Bob's help, but Bob just mocks Lisa. Later, Lisa realizes she herself has done all the murders. Bob is transferred to another prison cell to find Lisa waiting for her, revealing that a split personality emerged after the death of Bart and that she had committed all those murders in hopes of going to prison with Bob. To the music of ''H.M.S. Pinafore'', Lisa gleefully slashes Bob to death.

In Season 36’s “[[The Yellow Lotus]]”, Bob has a minor role, as he is shown to be married and in the same resort with the Simpsons. When Marge tells Bob’s wife about his previous deeds, she throws him off of a cliff, only for Bob to survive and talk with Sideshow Mel.

===Other media===
In addition to regular roles in the television series, Sideshow Bob has made several appearances in other ''Simpsons'' media. Kelsey Grammer recorded several Sideshow Bob lines for ''[[The Simpsons Movie]],'' but the scene was cut; the deleted scene shows him amongst the angry mob, intent on killing Bart until he learns that the mob is apparently after Homer only, prompting him to leave in disappointment.<ref name=moviesonline>{{cite news |title=The Simpsons: a to Z |author=Whipp, Glenn |date=July 28, 2007 |work=[[The Hamilton Spectator]]}}</ref> Sideshow Bob has made regular appearances in the monthly [[List of The Simpsons comics#Simpsons Comics|''Simpsons Comics'']],<ref>{{Cite web |url=http://www.harpercollins.com/books/9780061231261/Simpsons_Comics_Beach_Blanket_Bongo/index.aspx |title=Simpsons Comics Beach Blanket Bongo |publisher=[[HarperCollins]] |access-date=January 11, 2009}}</ref> and several of Kelsey Grammer's singing performances have been included in ''The Simpsons'' CD compilations. His performance of the ''[[H.M.S. Pinafore]]'' in "Cape Feare" was later included on the album ''[[Go Simpsonic with The Simpsons]],''<ref>{{cite web |url={{AllMusic |class=album |id=r431501 |pure_url=yes}} |title=Go Simpsonic with the Simpsons |access-date=February 10, 2007 |author=Erlewine, Stephen Thomas |website=AllMusic}}</ref> and the song "[[I've Grown Accustomed to Her Face|The Very Reason That I Live]]" from "The Great Louse Detective" was included on ''[[The Simpsons: Testify]]''.<ref name=billboard>{{cite magazine |url=http://www.billboard.com/articles/news/1050957/dozens-of-simpsons-songs-bundled-for-testify |title=Dozens Of 'Simpsons' Songs Bundled For 'Testify' |access-date=January 3, 2009 |magazine=[[Billboard (magazine)|Billboard]]}}</ref> A previously unaired song, "Hullaba Lula", originally written for "Day of the Jackanapes", was also included on that compilation.<ref name=billboard/> The producers modeled the song after "[[Zip-a-Dee-Doo-Dah]]", but were forced to remove the song from the episode when they were unable to obtain the rights to it.<ref>Jean, Al. (2009). Commentary for "Day of the Jackanapes", in ''The Simpsons: The Complete Twelfth Season'' [DVD]. 20th Century Fox.</ref>

In ''[[The Simpsons Game]]'', released in November 2007, Bob has a speaking [[cameo appearance]] at the end of the chapter titled "Invasion of the Yokel-Snatchers" in which he was working with [[Kang and Kodos]].<ref>{{cite web |url=http://wii.ign.com/articles/833/833630p1.html |title=The Simpsons Game Review |author=Ahearn, Nate |access-date=May 8, 2008 |date=November 8, 2007 |website=[[IGN]] |archive-url=https://web.archive.org/web/20080829150503/http://wii.ign.com/articles/833/833630p1.html |archive-date=August 29, 2008 |url-status=dead |df=mdy-all }}</ref> Sideshow Bob appears in the 1991 ''[[The Simpsons Arcade Game]]'', on the fifth level where he is pulling a cart containing a roast chicken health pick up. Bob was also included as a level boss in the 1991 video game ''[[The Simpsons: Bart vs. the Space Mutants|Bart vs. the Space Mutants]]''.<ref>{{cite web |url=http://cheats.ign.com/objects/009/009786.html |title=The Simpsons: Bart vs. the Space Mutants |access-date=October 12, 2007 |website=IGN}}</ref> Sideshow Bob plays a lead role in [[The Simpsons Ride]], which opened at [[Universal Studios Florida]] and [[Universal Studios Hollywood]] in May 2008. Voiced by Grammer, he is the main villain in the ride, having escaped from prison to get revenge on the Simpson family.<ref>{{cite news|url=http://travel.latimes.com/daily-deal-blog/index.php/simpsons-ride-featur-1657/ |title=Simpsons ride features 29 characters, original voices |access-date=May 8, 2008 |date=April 9, 2008 |work=[[Los Angeles Times]] |author=MacDonald, Brady |url-status=dead |archive-url=https://archive.today/20080914144851/http://travel.latimes.com/daily-deal-blog/index.php/simpsons-ride-featur-1657/ |archive-date=September 14, 2008 }}</ref><ref>{{cite news|url=http://www2.tbo.com/content/2008/may/02/bz-woo-hoo-itchy-for-fun-ride-with-the-simpsons/ |title=Woo Hoo! Itchy For Fun? Ride with the Simpsons |author=Belcher, Walt |access-date=April 30, 2008 |date=May 1, 2008 |work=[[Tampa Tribune]] |url-status=dead |archive-url=https://web.archive.org/web/20080505062933/http://www2.tbo.com/content/2008/may/02/bz-woo-hoo-itchy-for-fun-ride-with-the-simpsons/ |archive-date=May 5, 2008 }}</ref>

In ''[[The Simpsons: Tapped Out]]'', a [[city-building game]] released in February 2012, Sideshow Bob occurs as a bonus. Popping up every couple hours, the players are given a chance to tap on him to receive a small sum of money, and "send" him to jail. In a later update to the game, Sideshow Bob also has a stand in Krusty Land, where players get to pop balloons for a chance to win donuts and Krusty [[Ticket (admission)|tickets]]. The Simpsons: Tapped Out Terwilligers content update was released April 14, 2015 and has several references to the Simpsons episodes with Sideshow Bob. This game event was split in 3 acts and ended June 4, 2015. New characters, skins and costumes include Sideshow Bob, Cecil Terwilliger, Gino Terwilliger, Francesca Terwilliger, Dr. Robert Terwilliger Sr., Judith Onderdonk, Captain Bob, and Opera Krusty. Most of the event action takes place at Monsarno Research and Opera House.

==Character==

===Creation===
[[File:SideshowBobsfirstappearance.png|right|200px|thumb|Sideshow Bob in his first appearance in "The Telltale Head". His design was simple compared to later versions and would be refined for his appearance in "Krusty Gets Busted".]]
Sideshow Bob first appeared in "[[The Telltale Head]]", the eighth episode of [[The Simpsons (season 1)|season 1]]. His design was relatively simple compared to later incarnations, and his hairstyle was rounded. However, towards the end of the episode, he appears again, in a panning shot of a crowd, with his familiar hairstyle.<ref name="MooreTTH"/> His second appearance, and first major one, was in season 1's twelfth episode "[[Krusty Gets Busted]]", written by [[Jay Kogen]] and [[Wallace Wolodarsky]].{{sfn|Richmond & Coffman|1997 |pp=28–29}} Bob's design was updated for "Krusty Gets Busted"; as the episode's animation style evolved, director [[Brad Bird]] made the character of Sideshow Bob sleeker and more refined, to fit Grammer's voice technique.<ref name="SilvermanBW"/> Following the re-design, animators tried to redraw his scenes in "The Telltale Head", but had insufficient time before the show was produced.<ref name="MooreTTH">Moore, Rich. (2001). Commentary for "The Telltale Head", in ''The Simpsons: The Complete First Season'' [DVD]. 20th Century Fox.</ref>

Bob has no lines of dialogue during the first half of "Krusty Gets Busted"; the character's only communication takes the form of a [[slide whistle]]. This was designed to make Bob appear simplistic, so that when he finally spoke, viewers would be surprised to hear his sophisticated vocabulary.<ref name="JeanKGB">Jean, Al. (2001). Commentary for "Krusty Gets Busted", in ''The Simpsons: The Complete First Season'' [DVD]. 20th Century Fox.</ref> An early version of the script for "Krusty Gets Busted" called for [[James Earl Jones]] to voice Bob, but the producers instead selected [[Kelsey Grammer]].<ref name="BirdKGB">Bird, Brad. (2001). Commentary for "Krusty Gets Busted", in ''The Simpsons: The Complete First Season'' [DVD]. 20th Century Fox.</ref> For Bob's voice, Grammer performed an impression of theatre [[actor]] and [[Theatre director|director]] [[Ellis Rabb]]. Grammer had once worked for Rabb, whose "lamenting tones became [the] foundation for Sideshow Bob".<ref name="Grammer">Grammer, Kelsey. (2006). Commentary for "Brother From Another Series", in ''The Simpsons: The Complete Eighth Season'' [DVD]. 20th Century Fox.</ref><ref name=NuvoAllan>{{cite web |last=Allan |first=Marc |title=17 Reasons to Turn on the TV |url=http://www.nuvo.net/ScreensBlog/archives/2011/07/30/17-reasons-to-turn-on-the-tv |work=Nuvo Magazine |date=July 30, 2011 |access-date=August 3, 2011 |url-status=dead |archive-url=https://web.archive.org/web/20111015141244/http://www.nuvo.net/ScreensBlog/archives/2011/07/30/17-reasons-to-turn-on-the-tv |archive-date=October 15, 2011 }}</ref>

Sideshow Bob's full name is Robert Underdunk Terwilliger.<ref>{{cite news |last1=Oakley |first1=Bill |title=One of the defenses of Trump is — literally — a TV-cartoon joke |url=https://www.washingtonpost.com/outlook/2019/11/14/one-defenses-trump-is-literally-tv-sitcom-joke/ |newspaper=Washington Post |date=November 14, 2019}}</ref> His [[last name]] was first revealed in "Black Widower"<ref name="Black Widower"/> while his [[middle name]] was first revealed in "Sideshow Bob Roberts".<ref name="Roberts"/> Competing theories as to the origin of his name exist; some sources say he was named after the character Dr. Terwilliker, a megalomaniac outwitted by a boy named Bart in the film ''[[The 5,000 Fingers of Dr. T]]'' by [[Dr. Seuss]], but others say he was named after [[Terwilliger Boulevard]] in [[Portland, Oregon]].<ref>{{cite news|url=http://www.mtv.com/movies/news/articles/1565538/20070725/story.jhtml |title='Simpsons' Trivia, From Swearing Lisa To 'Burns-Sexual' Smithers |access-date=July 29, 2007 |date=July 26, 2007 |last=Carroll |first=Larry |publisher=[[MTV]] |url-status=dead |archive-url=https://web.archive.org/web/20071220140402/http://www.mtv.com/movies/news/articles/1565538/20070725/story.jhtml |archive-date=December 20, 2007 }}</ref><ref>{{cite web|url= http://www.oregonlive.com/movies/index.ssf/2012/05/the_simpsons_map_of_portland_w.html|date= May 7, 2012 |first= Joseph | last= Rose |title= 'The Simpsons' map of Portland |work= The Oregonian|quote= Southwest Terwilliger Boulevard: Just as the rush-hour traffic in the Terwilliger Curves never seems to go away, culturally sophisticated jailbird Sideshow Bob Terwilliger just keeps coming back in his quest to exact revenge on Bart. | access-date= August 2, 2014}}</ref><ref>{{cite web |url= http://www.hulu.com/the-simpsons-anniversary-special-in-3-d-on-ice |title=The Simpsons 20th Anniversary Special | archive-url= https://web.archive.org/web/20100114015750/http://www.hulu.com/the-simpsons-anniversary-special-in-3-d-on-ice| archive-date= January 14, 2010 |access-date=January 25, 2010 |date=January 10, 2010}}</ref> Yet another theory is that he was named after Sergeant Terwilliger and Mrs. Onderdonk in the pilot episode of the TV show ''[[Hunter (1984 American TV series)|Hunter]]''.<ref>[http://terminallaughter.ca/2010/05/06/terminal-laughter-plants-flag-on-unclaimed-simpsons-reference Unclaimed Simpsons Reference Finally Gotten] {{webarchive|url=https://web.archive.org/web/20100514162054/http://terminallaughter.ca/2010/05/06/terminal-laughter-plants-flag-on-unclaimed-simpsons-reference/ |date=May 14, 2010 }}</ref>

===Development===
For [[The Simpsons (season 3)|season three]]'s "[[Black Widower]]", the writers echoed the premise of [[Wile E. Coyote and the Road Runner|Wile E. Coyote chasing the Road Runner]] from ''[[Looney Tunes]]'' cartoons by having Bob unexpectedly insert himself into Bart's life and attempt to kill him. Executive producer [[Al Jean]] has compared Bob's character to that of Wile E. Coyote, noting that both are intelligent, yet always foiled by what they perceive as an inferior intellect.<ref name="JeanBW">Jean, Al. (2003). Commentary for "Black Widower", in ''The Simpsons: The Complete Third Season'' [DVD]. 20th Century Fox.</ref> For "Black Widower", director [[David Silverman (animator)|David Silverman]] updated the character model to reflect the animation of director Brad Bird.<ref name="SilvermanBW">Silverman, David. (2003). Commentary for "Black Widower", in ''The Simpsons: The Complete Third Season'' [DVD]. 20th Century Fox.</ref> A rule for earlier episodes featuring Bob called for a recap of his evil deeds; this was dropped after [[The Simpsons (season 8)|season eight]]'s "[[Brother from Another Series]]" when the chronology became too lengthy.<ref name="Weinstein">Weinstein, Josh. (2006). Commentary for "Brother From Another Series", in ''The Simpsons: The Complete First Season'' [DVD]. 20th Century Fox.</ref> Another rule established by the show's writers mandated Bob's return to prison at the end of each episode, although this pattern was abandoned in later episodes like "The Great Louse Detective" and "The Italian Bob".<ref name="Weinstein"/>
[[File:Kelsey Grammer - Cropped.jpg|left|thumb|[[Kelsey Grammer]] based Bob's voice on his experiences with actor [[Ellis Rabb]]. |alt=A man wearing a cap smiles broadly.]]
[[Bill Oakley]] and [[Josh Weinstein]], the [[showrunner]]s for the seventh and eighth seasons, believed that every season of the show should contain an episode starring Sideshow Bob. However, by the seventh season, Bob had already been the focus of four episodes, and writers were having trouble developing new ways to include him.<ref>Oakley, Bill. (2005). Commentary for "Sideshow Bob's Last Gleaming", in ''The Simpsons: The Complete Seventh Season'' [DVD]. 20th Century Fox.</ref> Weinstein describes Bob's dialogue as difficult to write, due to his unique and refined style of speaking.<ref>Weinstein, Josh. (2005). Commentary for "Sideshow Bob's Last Gleaming", in ''The Simpsons: The Complete Seventh Season'' [DVD]. 20th Century Fox.</ref> Despite these challenges, however, creators of ''The Simpsons'' usually look forward to "Sideshow Bob episodes"; the writers consider them enjoyable to write,<ref name="Keeler">Keeler, Ken. (2006). Commentary for "Brother From Another Series", in ''The Simpsons: The Complete Eighth Season'' [DVD]. 20th Century Fox.</ref> and former director [[Dominic Polcino]] describes them as "a treat" to work on.<ref name="Polcino">Polcino, Dominic. (2005). Commentary for "Sideshow Bob's Last Gleaming", in ''The Simpsons: The Complete Seventh Season'' [DVD]. 20th Century Fox.</ref> In "Black Widower", Sideshow Bob notes that he is a "life-long [[Republican Party (United States)|Republican]]".

Kelsey Grammer initially expected Sideshow Bob to be a one-time role, and calls him "the most popular character I've ever played".<ref name="Grammer"/> Grammer usually joins the show's "table readings" (wherein cast members read each script together for the first time),<ref name="JeanCF">Jean, Al. (2004). Commentary for "Cape Feare", in ''The Simpsons: The Complete Fourth Season'' [DVD]. 20th Century Fox.</ref> and former executive producer [[David Mirkin]] described working with Grammer as very pleasant, due to his lively sense of humor. Grammer, Mirkin says, is capable of perfect readings, but noted that the actor dislikes performing Sideshow Bob's evil laugh.<ref name="Mirkin">Mirkin, David. (2005). Commentary for "Sideshow Bob Roberts", in ''The Simpsons: The Complete Sixth Season'' [DVD]. 20th Century Fox.</ref> In a 2007 interview, ''Simpsons'' executive producer [[Al Jean]] listed Grammer as one of his favorite guest stars (second only to [[Phil Hartman]]), saying "his voice is so rich."<ref name="Star">{{cite news |url=https://www.thestar.com/news/2007/05/20/producer_speaks_out_on_cartoon_cameos.html |title=Producer speaks out on cartoon cameos |work=[[Toronto Star]] |access-date=October 13, 2007 |date=May 20, 2007}}</ref> Writer [[George Meyer]] commented that "writing for Kelsey is great, he can give the kind of purple, florid, melodramatic speeches that most of the characters would never give. And he can sing."<ref name="Guide">{{cite news |last=Rhodes |first=Joe |title=Flash! 24 Simpsons Stars Reveal Themselves |work=[[TV Guide]] |date=October 21, 2000|url=http://simpsonsarchive.com/other/articles/flash.html |access-date=August 15, 2007}}</ref>

The show's writers admire Grammer's singing voice, and try to include a song for each appearance.<ref name="JeanCF"/> [[Alf Clausen]], the primary composer for ''The Simpsons'', commented that "[Grammer] is so great. He's just amazing. You can tell he has this love of musical theater and he has the vocal instrument to go with it, so I know whatever I write is going to be sung the way I've heard it."<ref>{{Cite news |title=The man who makes 'The Simpsons' sing |url=http://www.cnn.com/2007/SHOWBIZ/TV/09/20/simpsons.clausen/index.html |publisher=[[CNN]] |author=Leopold, Todd |date=September 21, 2007 |access-date=January 3, 2009}}</ref> Clausen composed Sideshow Bob's theme, which is played whenever Bob gets out of prison or is about to commit a sinister action, and was first used in "[[Cape Feare]]". It is based on the score of the film ''[[Cape Fear (1962 film)|Cape Fear]]'', composed by [[Bernard Herrmann]].<ref name="JeanCF"/> The musical score for "Cape Feare" earned Clausen an [[Emmy Award]] nomination for [[Primetime Emmy Award for Outstanding Music Composition for a Series|Outstanding Dramatic Underscore – Series]] in 1994.<ref>{{cite web|url=http://www.emmys.org/awards/awardsearch.php |title=Primetime Emmy Awards Advanced Search |publisher=Emmys.org |access-date=October 17, 2007 |url-status=dead |archive-url=https://web.archive.org/web/20090403022947/http://www.emmys.org/awards/awardsearch.php |archive-date=April 3, 2009 }}</ref>

Bob's prisoner number is often 24601, which is [[Jean Valjean]]'s prisoner number in ''[[Les Misérables]]''.<ref name="Reiss">Reiss, Mike. (2003). Commentary for "Black Widower", in ''The Simpsons: The Complete Third Season'' [DVD]. 20th Century Fox.</ref> Another trademark for Bob is a visual gag of stepping on a rake and being struck in the face with its handle; this joke first appeared in "Cape Feare". To fill time, the writers added nine consecutive iterations of the same joke in quick succession.<ref name="JeanCF"/> The sequence has become known as the "rake joke" and was described by ''Entertainment Weekly'' as showing "genius in its repetitive stupidity."<ref name="EW"/>

===Family===
[[File:David Hyde Pierce - Cropped.jpg|thumb|right|upright|Sideshow Bob's brother Cecil was designed to resemble actor [[David Hyde Pierce]], who also played the brother of Grammer's character on the show ''Frasier''.]]
The episode "[[Brother from Another Series]]" introduces Bob's brother Cecil. After writer [[Ken Keeler]] was assigned to write an episode featuring Sideshow Bob, he drew inspiration from episodes of ''[[Frasier]]''. He decided to incorporate elements of Grammer's other show into the character of Sideshow Bob, and designed Cecil to resemble Grammer's brother on ''Frasier''.<ref name="Keeler"/> Cecil is voiced by [[David Hyde Pierce]], who portrayed [[Frasier Crane]]'s brother [[Niles Crane|Niles]]. Pierce commented, "Normally, I would not do something like this. But how often do you get a chance to work with an actor like Kelsey Grammer and, more importantly, play his brother?"<ref>{{Cite news |title=TV Tidbits |work=[[The Hamilton Spectator]] |date=February 20, 1997}}</ref> Several of ''Frasier''{{'s}} producers were asked to review the original script and provide feedback. Their comments were positive; they only expressed concern with a very brief scene in which Cecil talks to a visible character whom he refers to as "Maris". In ''Frasier'', [[Maris Crane]] is an [[unseen character]], and the producers of ''Frasier'' asked that the scene be removed.<ref name="Keeler"/> Many of the interactions between Bob and Cecil were based on those of Niles and Frasier.<ref name="Keeler"/> Cecil was drawn to resemble [[David Hyde Pierce]], while retaining a visual similarity to Sideshow Bob. According to director [[Pete Michels]], it was difficult to draw Bob and Cecil standing together, because of their comically oversized feet.<ref name="Michels">Michels, Pete. (2006). Commentary for "Brother From Another Series", in ''The Simpsons: The Complete Eighth Season'' [DVD]. 20th Century Fox.</ref>

Cecil returns in [[The Simpsons (season 19)|season 19]]'s "[[Funeral for a Fiend]]", which introduces the brothers' previously unseen father, Dr. Robert Terwilliger, played by [[John Mahoney]].<ref name="Futon">{{cite magazine |title=The Simpsons |magazine=[[Entertainment Weekly]] |date=September 4, 2007 |url=http://www.ew.com/ew/article/0,,20054579,00.html |access-date=January 1, 2009 |archive-date=February 4, 2009 |archive-url=https://web.archive.org/web/20090204020429/http://www.ew.com/ew/article/0,,20054579,00.html |url-status=dead }}</ref> Mahoney portrayed [[Martin Crane]], the father of Grammer's and Pierce's characters in ''Frasier''.<ref name=Frasierreunion>{{cite web |url=http://www.digitalspy.co.uk/tv/a75660/frasier-cast-to-reunite-for-simpsons.html |title=''Frasier'' cast to reunite for ''Simpsons'' |date=September 14, 2007 |author=Dadds, Kimberley |access-date=October 15, 2007 |work=Digital Spy}}</ref> Whereas in ''Frasier'', Mahoney played the "down-to-Earth, average guy" to Grammer's and Hyde Pierce's "uppity snobs", Robert Terwilliger Sr. was portrayed as equally highbrow as Bob.<ref>{{cite web |author=Canning, Robert |title=The Simpsons: "Funeral for a Fiend" Review |website=IGN |date=November 26, 2007 |url=http://tv.ign.com/articles/837/837504p1.html |access-date=January 3, 2009}}</ref> His wife, Bob's mother, is Dame Judith Onderdonk, "the finest classical actress of her generation." She sports the same curly spiked hair as her two sons. Bob also has a wife named Francesca (voiced by [[Maria Grazia Cucinotta]]) and a son named Gino, both of whom were introduced in [[The Simpsons (season 17)|season 17]] episode "[[The Italian Bob]]" and returned for "[[Funeral for a Fiend]]".<ref name="TIB"/>

==Reception==
[[File:Nancy Cartwright.jpg|thumb|right|upright|Actress [[Nancy Cartwright]], the voice of Bart Simpson, said in her book ''[[My Life as a 10-Year-Old Boy]]'' that Grammer's performance brings "deliciously vile energy" to the show.<ref name="Cartwright"/>]]

The character of Sideshow Bob and Grammer's voicework have received many accolades. In 2006, [[IGN]] listed him as the second-best "peripheral character" on ''The Simpsons'', commenting that Bob is "a man of contradictions; his goofy appearance, complete with palm tree like hair, doesn't seem to match up to the well spoken and even musically talented maniac."<ref>{{cite web|url=http://uk.tv.ign.com/articles/730/730957p5.html |title=Top 25 Simpsons Peripheral Characters |access-date=June 8, 2007 |date=September 6, 2006 |author1=Eric Goldman |author2=Dan Iverson |author3=Brian Zoromski |website=[[IGN]] |url-status=dead |archive-url=https://web.archive.org/web/20071031112102/http://uk.tv.ign.com/articles/730/730957p5.html |archive-date=October 31, 2007 }}</ref> Also that year, ''[[Wizard (magazine)|Wizard]]'' magazine rated Bob as the 66th-greatest villain of all time.<ref>{{cite journal |last=McCallum |first=Pat |date=July 2006 |title=100 Greatest Villains Ever |journal=[[Wizard (magazine)|Wizard]] |issue=177}}</ref> Adam Finley of [[TV Squad]] wrote that "that baritone voice, the Shakespearean delivery, and the ability to go from calm and collected to stark raving mad all within the same second make Sideshow Bob one of the best recurring characters on the show."<ref>{{Cite web |url=http://www.tvsquad.com/2006/06/20/the-five-great-simpsons-guest-stars/ |title=The Five: Great Simpsons guest stars |author=Finley, Adam |publisher=TV Squad |date=June 20, 2006 |access-date=January 3, 2009}}</ref>

Kelsey Grammer has consistently received praise for his voicework, and has been described as "brilliant",<ref>{{Cite news |title=300 reasons to love The Simpsons |work=[[The Courier-Mail]] |date=April 24, 2003 |author=McCollum, Charlie}}</ref> "inimitable"<ref>{{Cite news |title=Woo hoo!&nbsp;– Even past its prime 'The Simpsons' is still prime comedy |work=[[Chicago Tribune]] |author=Keveney, Bill |date=January 24, 2000}}</ref> and "a feast of mid-Atlantic anglophilia".{{sfn|Turner|2004|pp=129–131}} In 2006, Grammer won the [[Primetime Emmy Award]] for [[Primetime Emmy Award for Outstanding Voice-Over Performance|Outstanding Voice-Over Performance]] for his role in "[[The Italian Bob]]"; he had previously won four awards in the [[Primetime Emmy Award for Outstanding Lead Actor - Comedy Series|Outstanding Lead Actor in a Comedy Series]] category for his portrayal of the title role on ''Frasier''.<ref>{{cite news |url=https://www.cbc.ca/news/entertainment/grammer-nets-early-emmy-for-simpsons-villain-portrayal-1.574779 |title=Grammer nets early Emmy for Simpsons villain portrayal |access-date=October 12, 2007 |date=July 20, 2006 |publisher=[[Canadian Broadcasting Corporation|CBC Arts]] |url-status=live |archive-url=https://web.archive.org/web/20070828235309/http://www.cbc.ca/arts/story/2006/07/20/grammer-emmy-sideshowbob.html <!--Added by H3llBot--> |archive-date=August 28, 2007}}</ref> In 2008, Grammer was included in ''[[Entertainment Weekly]]''{{'}}s list of the sixteen best ''Simpsons'' guest stars; Hyde Pierce was also included in that list.<ref>{{cite magazine |title=Springfield of Dreams: 16 Great 'Simpsons' Guest Voices |magazine=Entertainment Weekly |date=May 11, 2008 |author=Wook, Kim |url=http://www.ew.com/ew/article/0,,20049408_14,00.html |access-date=May 11, 2008 |archive-date=October 12, 2013 |archive-url=https://web.archive.org/web/20131012030137/http://www.ew.com/ew/article/0,,20049408_14,00.html |url-status=dead }}</ref> Ken Tucker of ''Entertainment Weekly'' wrote that "Kelsey Grammer's grand voice-performance as Sideshow Bob is Frasier pickled in arsenic."<ref name="Arsenic">{{Cite magazine |title=The Family Dynamic&nbsp;– At 300 episodes and counting, the Simpsons&nbsp;– TV's answer to the great American novel&nbsp;– continues to be a show about everything |date=February 7, 2003 |author=Tucker, Ken |magazine=Entertainment Weekly |issue=694 |pages=28–43}}</ref> In her book ''[[My Life as a 10-Year-Old Boy]]'', [[Nancy Cartwright]] (who performs the voice of Bart Simpson) wrote that "Kelsey Grammer scores big-time by injecting caustic, bitter, contemptuous and deliciously vile energy into his rendition of Sideshow Bob. Springfield just wouldn't be the same without him."<ref name="Cartwright">{{cite book |last=Cartwright |first=Nancy |title=My Life as a 10-Year-Old Boy |year=2000 |publisher=[[Hyperion (publisher)|Hyperion]] |location=New York City |page=[https://archive.org/details/mylifeastenyearo00nanc/page/264 264] |isbn=978-0-7868-8600-5|title-link=My Life as a 10-Year-Old Boy }}</ref>

Most of the episodes featuring Bob have been well received by fans and critics. "[[Cape Feare]]" is generally regarded as one of the best episodes of ''The Simpsons''<ref name="groening">Groening, Matt. (2004). Commentary for "Cape Feare", in ''The Simpsons: The Complete Fifth Season'' [DVD]. 20th Century Fox.</ref> and placed third on ''Entertainment Weekly''{{'}}s 2003 list of the show's top 25 episodes.<ref name="EW">{{cite magazine |url=http://www.ew.com/ew/article/0,,417748~3~0~25bestand1,00.html |title=The Family Dynamic |access-date=October 12, 2007 |date=January 29, 2003 |magazine=Entertainment Weekly |archive-date=October 18, 2014 |archive-url=https://web.archive.org/web/20141018160211/http://www.ew.com/ew/article/0,,417748~3~0~25bestand1,00.html |url-status=dead }}</ref> IGN considers it the best episode of the fifth season.<ref name="IGN2">{{cite web|url=http://tv.ign.com/articles/731/731095p1.html |title=The Simpsons: 17 Seasons, 17 Episodes |author1=Goldman, Eric |author2=Dan Iverson, Brian Zoromski |website=IGN |date=September 8, 2006 |access-date=October 12, 2007 |url-status=dead |archive-url=https://web.archive.org/web/20070302212129/http://tv.ign.com/articles/731/731095p1.html |archive-date=March 2, 2007 }}</ref> In 2007, ''[[Vanity Fair (magazine)|Vanity Fair]]'' called it the show's fourth-best episode, because of its "masterful integration of filmic parody and a recurring character".<ref>{{cite news|author=Orvted|first=John|date=July 5, 2007|title=Springfield's Best|work=[[Vanity Fair (magazine)|Vanity Fair]]|url=https://www.vanityfair.com/news/2007/08/top10simpsons200708?currentPage=2|access-date=October 12, 2007}}</ref> [[Ben Rayner]] of the ''[[Toronto Star]]'' listed "Cape Feare", "Sideshow Bob's Last Gleaming" and "Brother From Another Series" among the best episodes of the series, writing "forget ''Frasier'', these are Kelsey Grammer's best roles."<ref name="Star2">{{cite news |url=https://www.thestar.com/entertainment/article/215831 |title=Eye on Springfield |author-link=Ben Rayner |author=Rayner, Ben |work=Toronto Star |access-date=October 13, 2007 |date=May 20, 2007 |archive-url=https://web.archive.org/web/20070615013522/http://www.thestar.com/entertainment/article/215831 |archive-date=June 15, 2007 |url-status=dead }}</ref> "[[The Italian Bob]]" and its writer [[John Frink]] won a [[Writers Guild of America Award]] in 2007 in the animation category.<ref>{{cite news |title=2007 Awards Winners |publisher=wga.org |url=http://www.wga.org/awards/awardssub.aspx?id=1517 |access-date=October 13, 2007 |archive-url=https://web.archive.org/web/20110221170524/http://www.wga.org/awards/awardssub.aspx?id=1517 |archive-date=February 21, 2011 }}</ref> In December 2009, Robert Canning of IGN ranked the ten episodes to feature Bob that had aired at the time. The first five Bob episodes took up the top five, with "Cape Feare" being ranked first. "The Italian Bob" was ranked tenth, with the explanation that "All the things we love about a Sideshow Bob episode—the vengeance, the familiar settings and characters, the elaborate scheming—were missing from this half-hour. Without it, Bob wasn't nearly as entertaining, and the episode didn't result in a whole lot of laughs." He noted that only "The Italian Bob" and the ninth ranked "Funeral for a Fiend" were "the only ones I'd consider clunkers. The remaining episodes are all quite fun."<ref>{{cite web |url=http://tv.ign.com/articles/105/1051182p1.html |author=Canning, Robert |date=December 2, 2009 |website=IGN |access-date=May 19, 2010 |title=The Simpsons: Top 10 Sideshow Bob Episodes}}</ref>

The character's line in "[[Sideshow Bob Roberts]]", "Attempted murder? Now honestly, what is that? Do they give a Nobel prize for attempted chemistry?", briefly became an [[Internet meme]] after a similar defense of President [[Donald Trump]] was repeated after the [[Trump–Ukraine scandal]].<ref>{{cite news | url=https://www.washingtonpost.com/outlook/2019/11/14/one-defenses-trump-is-literally-tv-sitcom-joke/ | title=One of the defenses of Trump is — literally — a TV-cartoon joke | first=Bill | last=Oakley | date=2019-11-14 | newspaper=[[The Washington Post]]}}</ref>

===Analysis===
In ''[[Planet Simpson]]'', author [[Chris Turner (author)|Chris Turner]] writes that Bob is built into a highbrow snob and conservative [[Republican Party (United States)|Republican]] so that the writers can continually use him as a strawman and pincushion. He represents [[high culture]] while Krusty represents [[low culture]], and Bart, stuck in between, always wins out.{{sfn|Turner|2004|pp=129–131}} In the book ''[[Leaving Springfield]]'', David L. G. Arnold comments that Bart is a product of a "mass-culture upbringing" and thus is Bob's enemy.<ref>[[#Arnold|Arnold]], pp. 2–3.</ref> Frustrated by his early role as the target of "Krusty's cheap gags", Bob frames Krusty and takes over the show. He changes the content of that show to present readings of classic literature and segments examining the emotional lives of pre-teens. He believes that by exposing the kids to high culture he will improve their lives.<ref name="p12"/> Arnold writes that "Bob's own conscience and morality are clearly unaffected by the high culture he represents." He also tries to "manipulate the tastes of the masses" by becoming a criminal mastermind.<ref name="p12">[[#Arnold|Arnold]], pp. 12–13.</ref> Arnold believes that this is most apparent in "[[Sideshow Bob Roberts]]", wherein he rigs the election to become the mayor of Springfield. When accused of election fraud, he rants, "Your guilty consciences may force you to vote Democratic, but secretly you yearn for a cold-hearted Republican who'll cut taxes, brutalize criminals, and rule you like a king! That's why I did this, to protect you from yourselves!" He considers himself a member of the social elite, and happily uses [[Machiavelli]]an methods to acquire and maintain power.<ref>[[#Arnold|Arnold]], p. 17.</ref>

Bob's intelligence serves him in many ways. During the episode "Cape Feare", for example, the parole board asks Bob why he has a tattoo that says "Die, Bart, Die". Bob replies that it is German for "The, Bart, The"; members of the board are impressed by his reasoning.<ref name=A16/> Believing that "nobody who speaks German could be an evil man", they release him.<ref name="Feare"/> However, his love of high culture is sometimes used against him. In the same episode, Bob agrees to perform the operetta ''[[H.M.S. Pinafore]]'' in its entirety as a last request for Bart. The tactic stalls Bob long enough for the police to arrest him.<ref name=A16>[[#Arnold|Arnold]], p. 16.</ref>

==Notes==
{{notelist}}

==References==
{{reflist}}

==Bibliography==
{{refbegin}}
*{{cite book |last=Arnold |first=David L. G. |editor=John Alberti|year=2003 |title=Leaving Springfield: The Simpsons and the Possibility of Oppositional Culture |location=Detroit |publisher=[[Wayne State University Press]] |chapter=Use a Pen, Sideshow Bob: The Simpsons and the Threat of High Culture |isbn=978-0-8143-2849-1|ref=Arnold|title-link=Leaving Springfield }}
*{{cite book |last=Groening |first=Matt |author-link=Matt Groening |editor1-first=Ray |editor1-last=Richmond |editor1-link=Ray Richmond |editor2-first=Antonia |editor2-last=Coffman |title=The Simpsons: A Complete Guide to Our Favorite Family |edition=1st |year=1997 |location=New York |publisher=[[HarperPerennial]] |lccn=98141857 |ol=433519M |oclc=37796735 |isbn=978-0-06-095252-5 |ref={{harvid|Richmond & Coffman|1997}}|title-link=The Simpsons episode guides#The Simpsons: A Complete Guide to Our Favorite Family }}
*{{cite book |last=Turner |first=Chris |author-link=Chris Turner (author) |title=Planet Simpson: How a Cartoon Masterpiece Documented an Era and Defined a Generation |others=Foreword by [[Douglas Coupland]]. |edition=1st |year=2004 |location=Toronto |publisher=[[Random House Canada]] |oclc=55682258 |isbn=978-0-679-31318-2|title-link=Planet Simpson }}
*{{cite book |last=Groening |first=Matt |author-link=Matt Groening |title=Simpsons World: The Ultimate Episode Guide: Seasons 1–20 |title-link=Simpsons World: The Ultimate Episode Guide: Seasons 1–20 |date=2010-10-28 |publisher=[[HarperCollins]] |isbn=9780061711282 |editor1-last=Richmond |editor1-first=Ray |editor1-link=Ray Richmond |edition=1st |editor2-last=Gimple |editor2-first=Scott M. |editor2-link=Scott M. Gimple |editor-last3=McCann |editor-first3=Jessie L. |editor-last4=Seghers |editor-first4=Christine |editor-last5=Bates |editor-first5=James W.}}
{{refend}}

{{Simpsons Sideshow Bob}}
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