Dr. Robert Underdunk "Bob" Terwilliger Jr., PhD, 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". A self-proclaimed genius and graduate of Yale University, Bob champions high culture and speaks with a transatlantic accent similar to the one Grammer uses as Dr. Frasier Crane in 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. After Bart exposes him, Bob begins seeking revenge, and the two become archenemies.
Bob's second major appearance came in season three's "Black Widower" by bringing him back into Bart's life with another murderous scheme, the writers established a pattern they likened to Wile E. Coyote's pursuit of the Road Runner. Thereafter, Bob serves as the series' recurring evil genius, repeatedly emerging from prison with elaborate revenge schemes that Bart and Lisa usually foil. Bart remains his principal target, although his schemes also threaten Krusty and, in "The Italian Bob" (season 17), the entire Simpson family. The Halloween story "Wanted: Dead, Then Alive", the first segment of "Treehouse of Horror XXVI" (season 27), imagines Bob finally killing Bart. Before the murder, he remarks that he has spent 24 years trying to kill a ten-year-old child; with Bart dead, he soon becomes bored and brings him back to life so that he can kill him repeatedly.
Sideshow Bob shares traits with Grammer's Crane and has been described as "Frasier pickled in arsenic." The resemblance extends to the casting: David Hyde Pierce and John Mahoney played Cecil and Robert Terwilliger Sr., Bob's brother and father, respectively, echoing their roles in Frasier. Grammer, who based Bob's voice on that of actor Ellis Rabb, has been praised for his portrayal of Bob. In 2006, Grammer won a Primetime Emmy Award for voicing Sideshow Bob.
By season 36, Sideshow Bob had appeared in dozens of episodes, including both speaking roles and silent cameos. "Treehouse of Horror XXXIV" centered a story on Bob during the 35th season, and he had another speaking appearance in "The Yellow Lotus" in the 36th season. Other episodes refer to Bob without featuring him, and his role goes beyond television into other Simpsons media. He appears in the Simpsons Comics and the 2007 video game The Simpsons Game; he also stars as the main antagonist in The Simpsons Ride at Universal Studios' theme parks. A lover of Gilbert and Sullivan operettas, Sideshow Bob is also known for his singing voice; several of Grammer's performances have been included in The Simpsons musical compilations.
Appearances
Seasons 1–8 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 appears among the town-square mob that confronts Bart Simpson after he returns the head. After Krusty subjects Bob to repeated abuse, including shooting him from a cannon, 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 removed from the show 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 take her stock-market money. Bob plans to kill Selma with a gas explosion triggered by her cigarette, but Bart again foils the plan, and Sideshow Bob returns to prison.
In "Cape Feare" (season 5, 1993), Bob targets Bart directly. 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 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. Police arrest him.
In "Sideshow Bob Roberts" (season 6, 1994), Bob is released again and runs for mayor of Springfield as the populist Republican Party candidate. He defeats Democratic Party incumbent Joe Quimby, winning in a landslide. 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. In "Sideshow Bob's Last Gleaming" (season 7, 1995), Bob escapes from prison and threatens to blow up Springfield with a nuclear bomb unless the city stops broadcasting all television shows. When the bomb proves to be a dud, Bob kidnaps Bart and takes to the air in the Wright brothers' plane, intending to kill himself, Bart, and Krusty. Krusty, Bob's intended target, is hiding inside a shack, improvising a performance on the Emergency Broadcast System. That attempt also fails, and Bob is captured.
Bob appears to have reformed and helps Bart and Lisa in "Brother from Another Series" (season 8, 1997). Reverend Lovejoy calls him a "model prisoner" and recommends him for the prison's work release program. Bob is reunited with his brother Cecil, now Springfield's chief hydrological and hydrodynamical engineer. Cecil resents Bob because Krusty chose Bob over him as sidekick. Seeking to frame his brother, Cecil sabotages the Springfield Dam in an attempt to flood the town. Bob, Bart, and Lisa stop Cecil and save the town, but both brothers are sent to prison despite Bob's innocence.
Seasons 12–19 Bob returns in "Day of the Jackanapes" (season 12, 2001), once again setting his sights on Krusty. While in prison, he learns that Krusty has erased all the early shows featuring Sideshow Bob. Annoyed by the network executives, Krusty announces his retirement. Once at large, Bob develops a plot to kill Krusty using Bart as a suicide bomber during Krusty's retirement special. Just as Bob is about to kill Bart and Krusty, he hears Krusty publicly accept responsibility for turning him into a criminal and express regret for mistreating him as a sidekick. Krusty's conciliatory song disarms Bob, who abandons the murder plot and reconciles with his former employer, though his part in the scheme still sends him back to prison. Bob again helps the Simpsons in "The Great Louse Detective" (season 14, 2002), when Springfield police enlist the jailed Bob to investigate an attempt on Homer Simpson's life. During the adventure, Bob resolves to kill Bart without delay. After the culprit is revealed to be Frank Grimes's son, Bob again turns his attention to murdering Bart. However, Bob finds he is "accustomed to his [Bart's] face" and cannot do it.
By "The Italian Bob" (season 17, 2005), Bob has fashioned a new life in Italy. He is now mayor of the Tuscan village of Salsiccia,: Ranked-list entry: the Simpsons came across Bob as the happy mayor of a small village, until Lisa divulged that Bob was an attempted-murderer. husband to Francesca, and father to Gino. The Simpson family, in Italy to retrieve a car for Mr. Burns, encounters him by chance. Bob welcomes them on the condition that they not reveal his criminal past; a drunken Lisa nevertheless calls Bob a wanted killer and exposes his prison uniform, turning the villagers against him. Bob then resolves to kill the entire Simpson family rather than Bart alone. When Francesca and Gino catch up with Bob, they join his vendetta. Bob's father, Robert Terwilliger Sr., and mother, Dame Judith Underdunk, join the vendetta in "Funeral for a Fiend" (season 19, 2007). Cecil also joins the plot. Bob initially attempts to kill the Simpson family again, but his plan fails. Having staged his own death during his trial, Bob locks Bart in the coffin and attempts to cremate him at the otherwise empty funeral home, to the maniacal laughter of the assembled Terwilligers. Lisa and the rest of the Simpson family foil the plot, and the Terwilligers are arrested.
Seasons 20–26 In "Sex, Pies and Idiot Scrapes" (season 20, 2008), Bob is listed among the criminals sought by Homer and Ned Flanders as bounty hunters, although he is still in prison; he escapes at the end of the episode. In "Wedding for Disaster" (season 20, 2009), a keychain bearing the initials “S” and “B” leads Bart and Lisa to suspect that Bob has kidnapped Homer to stop him from marrying Marge again. Krusty, however, confirms that Bob was with him all day. The children eventually discover the true culprits, Patty and Selma. Bob also appears in a visual joke in "Coming to Homerica", the 21st episode of the season: the Simpson family enters the Cheers bar dressed as the show's cast, followed by Sideshow Bob dressed as Frasier Crane. In "O Brother, Where Bart Thou?" (season 21, 2009), Bob and Cecil make a silent cameo, flying kites in Bart's dream sequence as he longs for a younger brother.
Later that season, Bob resumes his attempts to kill Bart in "The Bob Next Door". 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 plans to use multiple state lines to evade prosecution for killing Bart, but he is foiled again and taken away by state police. Bob next appears in "At Long Last Leave" (season 23, 2012), the 500th episode of The Simpsons. He attends a town meeting to decide if the Simpson family should be banished from Springfield and joins many residents in supporting the proposal. He makes a silent appearance in "Moonshine River" (season 24, 2012), where he runs across the train tracks trying to kill Bart and is struck by a train.
In "The Man Who Grew Too Much" (season 25, 2014), Bob has become chief scientist at Monsarno, a chemical engineering company, after serving as a test subject and publishing the results of experiments performed on him. He and Lisa bond over their interest in Walt Whitman, but Bob reveals that he has modified his own genes to acquire several superhuman abilities. He plans to use DNA from historical figures' relics in the Springfield Museum to transform himself into a superhuman dictator. After a family repeatedly asks him to take another photograph, Bob chases down Bart and Lisa in a murderous rage. Before he can kill them, teenagers from Marge's abstinence class attack him. Lisa quotes Whitman during the fight; confronted with what he has become, Bob jumps off the Springfield Dam. The final shot reveals Bob alive underwater, breathing through the gills he engineered. The A.V. Club found the experimentation too cartoonish even for The Simpsons, while TV Fanatic called the transformation "silly even for him".
Bob is back in prison in "Clown in the Dumps" (season 26, 2014). He offers his condolences to Krusty following the death of Krusty's father, Rabbi Krustofsky. Several episodes later, in "Blazed and Confused" (season 26, 2014), Bob meets Bart's former teacher Mr. Lassen. Now a prison guard after losing his teaching job through Bart's actions at a "Blazing Guy" festival, Lassen offers to free Bob if they team up and take turns gutting Bart. Bob declines.
Seasons 27–36