Sideshow Bob

Appearances

On The Simpsons

Sideshow Bob first appears in "The Telltale Head" (season 1, 1990) as a non-speaking sidekick who communicates only through a slide whistle on Krusty the Clown's television show. After the head is stolen from Jebediah Springfield's statue, Krusty encourages his viewers to identify the thief. Bob joins the town mob after the townspeople discover that Bart Simpson took it. After Krusty subjects Bob to repeated abuse, including shooting him from a cannon and pelting him with pies, the Yale-educated Bob grows angry with his employer and resentful of the clown's success.

In "Krusty Gets Busted" (season 1, 1990), Bob turns on Krusty, disguising himself as the clown and framing 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.

In "Black Widower" (season 3, 1992), Bob, prisoner number 24601, is released from prison. He marries Bart's aunt Selma Bouvier as part of a scheme to inherit money she has 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.

In "Cape Feare" (season 5, 1993), Bob targets Bart himself for the first time. After being paroled, he threatens Bart repeatedly and forces the Simpsons into hiding as part of the Witness Relocation Program. Bob follows them to their hideout, a houseboat on Terror Lake, and, after subduing the family, prepares to kill Bart. Bob grants Bart one final request, and Bart asks to hear him sing the entire score of H.M.S. Pinafore. Bob finishes singing and nearly kills Bart, but the delay allows the houseboat to drift back to Springfield, where police arrest him for the third time.

In "Sideshow Bob Roberts" (season 6, 1994), Bob is released again and runs for mayor of Springfield as the populist Republican Party candidate (having previously identified himself as "a lifelong Republican" in "Black Widower"). He defeats Democratic Party incumbent Joe Quimby in a landslide, but Bart and Lisa learn from Waylon Smithers that Bob rigged the election by using the names of deceased people. At trial, Bob claims innocence, but Bart and Lisa trick him into revealing his guilt, sending him back to prison.

Other media

Outside the television series, Bob appears with Disney villains in the 2024 Disney+ animated short film The Most Wonderful Time of the Year.

Kelsey Grammer recorded several Sideshow Bob lines for a scene ultimately cut from The Simpsons Movie. In the deleted scene, Bob joins an angry mob intent on killing Bart, then leaves in disappointment after learning that it is apparently targeting only Homer. Sideshow Bob has also appeared in Simpsons Comics.

Several of Kelsey Grammer's singing performances have been included in The Simpsons CD compilations. His performance of H.M.S. Pinafore in "Cape Feare" later appeared on the album Go Simpsonic with The Simpsons, and the song "The Very Reason That I Live" from "The Great Louse Detective" appeared on The Simpsons: Testify. A previously unaired song, "Hullaba Lula", originally written for "Day of the Jackanapes", also appeared on The Simpsons: Testify. The producers modeled the song after "Zip-a-Dee-Doo-Dah", but removed it from the episode after failing to secure the necessary rights.

Sideshow Bob appears in the 1991 The Simpsons Arcade Game, where he is one of the Springfield characters who walk past the players. Bob is also named among the antagonists in the 1991 video game Bart vs. the Space Mutants. In The Simpsons Game, released in November 2007, Bob has a cameo appearance. Bob has a larger 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.

In The Simpsons: Tapped Out, a city-building game released in February 2012, Sideshow Bob appears as a bonus character. Bob pops up every so often, giving players 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 Krustyland, where players get to pop balloons for a chance to win donuts and Krusty tickets. The Terwilligers content update for The Simpsons: Tapped Out was released on April 14, 2015, and contained several references to episodes of The Simpsons featuring Sideshow Bob. The event was split into three acts and ended May 26, 2015. New characters, skins, and costumes included Sideshow Bob, Cecil Terwilliger, Gino Terwilliger, Francesca Terwilliger, Dr. Robert Terwilliger Sr., Dame Judith Underdunk, Captain Bob, and Opera Krusty. Most of the event action took place at Monsarno Research and Outdoor Opera Stage.

Character

Creation

Sideshow Bob first appeared in "The Telltale Head", the eighth episode of season 1. His original design was simpler than later versions and featured a rounded hairstyle. Toward the end of the episode, however, he reappears in a panning shot of a crowd with his now-familiar newer hairstyle. His second appearance—and his first major one—came in season 1's twelfth episode, "Krusty Gets Busted", written by Jay Kogen and Wallace Wolodarsky. Bob's design was updated for "Krusty Gets Busted"; as the episode's animation style evolved, director Brad Bird made Bob sleeker to fit Grammer's vocal performance. Following the redesign, animators tried to redraw his scenes in "The Telltale Head" but lacked time before production ended. Director David Silverman also updated the character model for "Black Widower" to reflect Brad Bird's animation style. Bird particularly enjoyed animating Bob and Krusty, whom he found "really absurd and strangely real". He asked to provide key drawings for selected scenes in their episodes.

Bob does not speak during the first half of "Krusty Gets Busted"; he communicates only through a slide whistle. The whistle was intended to make him seem simplistic so that his sophisticated vocabulary would surprise viewers when he finally spoke. 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.

Grammer was then playing Frasier Crane on Cheers, where Simpsons co-developer Sam Simon had heard him sing. Simon advocated casting him as Bob.

According to Grammer, Simon telephoned to ask him to sing Cole Porter's "Ev'ry Time We Say Goodbye", explaining, "we want him [Sideshow Bob] to speak finally".

For Bob's voice, Grammer performed an impression of theater actor and director Ellis Rabb.

Grammer had once worked for Rabb, whose "lamenting tones became [the] foundation for Sideshow Bob". His work included painting Rabb's apartment and hanging wallpaper; he listened to the actor's stories. He recalled thinking, "I'm gonna use him someday". Bob's taste for Cole Porter in the script reminded Grammer of Rabb.

Sideshow Bob's full name is Robert Underdunk Terwilliger Jr., PhD. His surname is revealed in "Black Widower", and his middle name in "Sideshow Bob Roberts". In 2024, Bill Oakley said that he and Josh Weinstein had written the middle name as "Onderdonk", rather than "Underdunk". He traced it to Henry Onderdonk, whose name they had found in a hymnal at high school. Larry Carroll of MTV Movie News reported that Bob's surname came from Dr. Terwilliker, a megalomaniacal piano teacher in the film The 5,000 Fingers of Dr. T., co-written by Dr. Seuss. The Oregonian has also associated the name with Southwest Terwilliger Boulevard in Portland, Oregon.

Development

For season three's "Black Widower", the writers echoed the premise of Wile E. Coyote chasing the Road Runner from Looney Tunes cartoons by having Bob unexpectedly reenter Bart's life through his marriage to Selma, whom he plans to murder. Executive producer Al Jean has compared Bob's character to that of Wile E. Coyote, noting that both are intelligent yet always foiled by opponents they perceive as intellectually inferior. Oakley and Weinstein chose a mayoral campaign instead of another murder plot for "Sideshow Bob Roberts" (1994).

Bill Oakley and Josh Weinstein, the showrunners for the seventh and eighth seasons, believed that each season should include a Sideshow Bob episode. By season seven, however, four Bob-centered episodes had already aired, and the writers struggled to find new uses for him. Weinstein described Bob's refined dialogue as difficult to write. Despite the challenge, the staff relished "Sideshow Bob episodes", and former director Dominic Polcino described them as "a treat" to work on. In 2014, Jean said he would approve another Bob episode only if the writers found a good new use for him, to avoid overusing the character.

Oakley recalled that the writers expected Bob's apparent reform in "Brother from Another Series" (1997) to be temporary: "we figured that would revert back". A rule for earlier episodes featuring Bob called for a recap of his evil deeds; this was dropped after season eight's "Brother from Another Series" when the chronology became too lengthy. The writers also initially required Bob to return to prison at the end of each episode, although they abandoned this pattern in later episodes such as "The Great Louse Detective" and "The Italian Bob". In 2020, Jean said he liked the idea of Bob exiled to a lighthouse, "thinking about the life that he wasted".

For "Treehouse of Horror XXVI" (2015), Jean used the noncanonical Halloween format to let Bob kill Bart without removing him from the regular series. He welcomed the outcome, recalling his childhood wish that the Coyote would catch the Road Runner. The story then explored how Bob would feel after achieving his life's ambition. For "Treehouse of Horror XXXIV" (2023), co-showrunner Brian Kelley said the writers first imagined Bob in an alternate future. Writer Jessica Conrad then proposed storytelling and visuals inspired by David Fincher's films.

Kelsey Grammer initially expected Sideshow Bob to be a one-time role but has called him "the most popular character I've ever played". Grammer usually joins the show's "table readings" (where cast members read each script together for the first time), and former executive producer David Mirkin has described Grammer as very pleasant to work with because of his lively sense of humor. Mirkin says that Grammer is capable of perfect readings but notes that the actor dislikes performing Sideshow Bob's evil laugh. 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." Writer George Meyer said that writing for Grammer was "great", adding, "He can give the kind of purple, florid, melodramatic speeches that most of the characters would never give. And he can sing."

Family

The episode "Brother from Another Series" introduces Bob's brother Cecil. Assigned to write an episode featuring Sideshow Bob, Ken Keeler drew on Frasier and modeled Cecil on the brother of Grammer's character. Cecil is voiced by David Hyde Pierce, who portrayed Frasier Crane's brother Niles. Many of the interactions between Bob and Cecil were based on those of Niles and Frasier. 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?"

Several of Frasier's producers were asked to review the original script and provide feedback. Their only concern was a brief scene in which Cecil addresses a visible character as "Maris". Because Maris Crane is an unseen character in Frasier, they asked for the scene to be removed. The artists drew Cecil 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.

Cecil returns in season 19's "Funeral for a Fiend", which introduces the brothers' previously unseen father, Dr. Robert Terwilliger, played by John Mahoney. Mahoney portrayed Martin Crane, the father of Grammer's and Pierce's characters in Frasier. In Frasier, Mahoney's "down-to-earth, average guy" served as a foil to Grammer's and Hyde Pierce's "uppity snobs"; Robert Terwilliger Sr. is as highbrow as Bob. Robert Terwilliger Sr.'s wife, Bob's mother, is Dame Judith Underdunk, "the finest classical actress of her generation." She sports the same curly, spiked hair as her two sons. Bob also has an ex-wife named Francesca (voiced by Maria Grazia Cucinotta) and a son named Gino, both of whom were introduced in the season 17 episode "The Italian Bob" and returned for "Funeral for a Fiend".

Cucinotta also voiced Francesca in Italian.

Blake Taylor of /Film wrote that introducing a wife and son gave Bob greater depth while keeping him a villain. Gino shares his father's appearance, manner of speaking, and cruelty, while Francesca joins them in their hostility to the Simpsons. Literary scholar Maria Elisa Montironi reads the father–son resemblance as a parallel with Shakespeare's Coriolanus. She notes that Gino's angry pursuit of a butterfly recalls young Marcius, whose violence is taken as evidence of his father's temperament.

Reception

The character of Sideshow Bob and Grammer's voice work 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." Also that year, Wizard magazine rated Bob as the 66th-greatest villain of all time. Adam Finley of TV Squad praised Bob's baritone voice, Shakespearean delivery, and ability to go from calm to "stark raving mad" within a second, calling him one of the show's best recurring characters.

In a 2020 retrospective, The Independent called Bob "the perfect Simpsons antagonist". It wrote that his vocabulary and love of Gilbert and Sullivan let the show's writers "indulge their artier inclinations", while his villainy was tempered by "vaudevillian buffoonishness". Reviewing "Black Widower", The A.V. Club wrote that Grammer "manages to make a prissy elitist scary" and praised the "musicality" and "poetry" of his performance. A 2014 A.V. Club review likewise found that Grammer could still make Bob "vitally funny and menacing" 24 years after the character's debut.

Kelsey Grammer's voice work has consistently received praise; Sideshow Bob has been described as "brilliant", "inimitable", "stentorian", and "a feast of mid-Atlantic anglophilia". In 2006, Grammer won the Primetime Emmy Award for Outstanding Voice-Over Performance for his recurring role as Sideshow Bob. He had previously won four awards in the Outstanding Lead Actor in a Comedy Series category for his portrayal of the title role on Frasier. In 2007, Grammer was included in Entertainment Weekly's list of the sixteen best Simpsons guest stars; Hyde Pierce was also included in that list. Ken Tucker of Entertainment Weekly wrote that "Kelsey Grammer's grand voice-performance as Sideshow Bob is Frasier pickled in arsenic." 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."

Erik Adams of The A.V. Club credited Grammer with developing Bob beyond his obsession with killing Bart. Reviewing "Sideshow Bob Roberts", he called Bob a "full-fledged character" whose desire for control extended to humanity as a whole. "Brother from Another Series" reverses Bob's usual relationship with Bart: Bob is innocent and tries to save Springfield while Bart stalks him. Fellow A.V. Club reviewer Gwen Ihnat called the episode a "turning point" in their relationship and suggested that the two were more alike than they thought. Writing for The A.V. Club, Nathan Rabin described Bob as a snob driven by "over-class rage", but argued that he was right to want better television that respected children's intelligence. The joke, in Rabin's view, is that Bob will frame and murder people to achieve those aims. He praised Grammer for bringing out the "aristocratic rage" beneath Bob's good manners.

Analysis

In Planet Simpson, author Chris Turner writes that portraying Bob as a highbrow snob and conservative Republican allows the writers to use him repeatedly as a straw man and pincushion. Bob represents high culture, while Krusty represents low culture; Bart occupies the middle ground and always prevails. 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. Frustrated by his early role as the target of "Krusty's cheap gags", Bob frames Krusty and takes over the show. He changes the show's content to present readings of classic literature and segments examining the emotional lives of preteens. He believes that by exposing children to high culture, he will improve their lives. Arnold writes that "Bob's own conscience and morality are clearly unaffected by the high culture he represents." Through his criminal schemes, he also tries to "manipulate the tastes of the masses".

Arnold considers this manipulation most apparent in "Sideshow Bob Roberts", in which Bob rigs the election to become 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!" Bob considers himself part of the social elite and uses Machiavellian methods to gain and retain power.

Writing about the film parody "Cape Feare" and Anne Washburn's Mr. Burns, a Post-Electric Play, a play based on the episode, Hans Vermy sees Bob's conflict with Bart as a rivalry between theater and television. He describes Bob as a frustrated artist whose formal speech and taste for theatrical tragedy and comedy contrast with his supporting role on Krusty's show. Bart represents both television's audience and its "champion". Bob wants Krusty's place in the spotlight, and Bart becomes a substitute target for his resentment. Vermy reads their conflict as a "competition between media: fatal contests for applause and audience".

Bob's intelligence serves him in many ways. In "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. Believing that "nobody who speaks German could be an evil man", they release him. His love of high culture can also work against him. In the same episode, Bob agrees to perform the operetta H.M.S. Pinafore in its entirety to fulfill Bart's last request. The performance delays Bob long enough for the police to arrest him.