Dr. Robert Underdunk "Bob" Terwilliger, PhD, better known as Sideshow Bob, is the secondary 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 who adopts a transatlantic accent similar to the one Grammer uses in his portrayal of 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 season three's "Black Widower"; the writers echoed the premise of Wile E. Coyote chasing the Road Runner by having Bob unexpectedly insert himself into Bart's life, threatening to disrupt it and ultimately murder him. Starting with that appearance, Bob has assumed the role on The Simpsons of an 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. His plans often involve death and destruction, usually targeted at Bart or, less often, Krusty, though he starts targeting the entire Simpson family in season 17. In 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, but he becomes bored with Bart dead, so he brings him back to life so that he can kill Bart repeatedly.

Despite his villainous deeds, Sideshow Bob shares some personality traits of Grammer's character Frasier Crane, and he has been described as "Frasier pickled in 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, Grammer won a Primetime Emmy Award for voicing Sideshow Bob.

As of season 36, Sideshow Bob has appeared in more than 40 episodes, made speaking appearances in 25 of these, and been featured as the main character in 15. The most recent of these main-character appearances, "Treehouse of Horror XXXIV", aired during the 35th season, and his most recent speaking appearance was in "The Yellow Lotus" in the 36th season. 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 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

On The Simpsons

The character of Sideshow Bob began his career as the non-speaking sidekick who communicated only with a slide whistle on Krusty the Clown's television show. Bob first appears in "The Telltale Head" (season 1, 1990). In the episode, Krusty offers a free slide whistle to anyone who identifies the person who stole the head of Jebediah Springfield's statue, and Bob joins the town mob when it is discovered that Bart Simpson took it. However, after repeated instances of abuse, including being shot from a cannon and hit constantly with pies, the Yale-educated Bob becomes angry with Krusty and resentful of the clown's success. In "Krusty Gets Busted" (season 1, 1990), Bob disguises himself as Krusty and frames 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.

"Black Widower" (season 3, 1992) is Bob's first major appearance after framing Krusty. In the episode, he is released from prison and 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. After being paroled from prison in "Cape Feare" (season 5, 1993), Bob targets Bart directly, threatening him repeatedly and forcing 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. 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 has drifted all the way back to Springfield.

Bob is released from prison once again in "Sideshow Bob Roberts" (season 6, 1994) and runs for mayor of Springfield as the 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 discover from Waylon Smithers that Bob rigged the election by using the names of deceased people. Bob is put on trial and claims to be innocent, but is tricked by Bart and Lisa into revealing his guilt, leading to another incarceration. Sideshow Bob escapes from prison for the first time in "Sideshow Bob's Last Gleaming" (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 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.

In the following season, Bob takes advantage of the prison's work release program and appears to be genuinely redeemed. "Brother from Another Series" (season 8, 1997) reveals that Bob only became Krusty's sidekick after his younger brother Cecil failed an audition ten years prior, because Krusty considered Bob to be a perfect comic foil. 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's chief hydrological and hydrodynamical engineer. However, the scheming Cecil, still smarting over his failed audition for Krusty, tries to frame Bob by sabotaging the Springfield Dam so that it bursts and floods Springfield. Bob, Bart, and Lisa together stop Cecil and save the town, and both brothers, despite Bob's genuine innocence, are sent to prison.

Bob returns in "Day of the Jackanapes" (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 network executives. Bob is released from prison and develops a plot to kill Krusty using Bart as a suicide bomber during Krusty's retirement special. Everything goes just as Bob planned, and just when Bob is about to succeed in murdering both his enemies, he overhears Krusty publicly holding himself responsible for turning Bob into a criminal, expressing his regret for mistreating Bob during his years as Sideshow. To make amends, Krusty sings a song to Bob, and being touched by this, Bob decides to abort his murder plan and reconciles with Krusty, although he is returned to prison for the murder plot. Bob's aid is sought by Springfield police in "The Great Louse Detective" (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 advised to kill Bart without hesitation rather than allow himself to be tricked into delaying or otherwise bungling his plans. When the mystery is solved (the culprit was Frank Grimes's son), he returns intending to murder Bart. However, Bob finds he is "accustomed to his [Bart's] face" and cannot do it.

In "The Italian Bob" (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 married a local woman named Francesca, with whom he has a son named 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 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 goal from killing Bart to killing the whole Simpson family. Upon catching up to Bob, his wife and son join him in declaring a vendetta against the entire Simpson family. The Terwilliger family appears together in "Funeral for a Fiend" (season 19, 2007), in which Bob's father, Robert Terwilliger Sr., and mother, Dame Judith Onderdonk, make their first appearances. Cecil also appears a second time on the show. Bob initially attempts to kill the Simpson family again, but his plan fails. Bob fakes his own death during his trial, locks Bart in the coffin, and attempts to cremate him 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.

In "Sex, Pies and Idiot Scrapes" (season 20, 2008), Bob is one of the wanted criminals whom Homer and Ned Flanders pursue in their work as bounty hunters, despite his already being in prison; he escapes at the end of the episode. In "Wedding for Disaster" (season 20, 2009), Bart and Lisa initially suspect Bob of kidnapping Homer to prevent him from attending his second wedding with Marge because they find a keychain bearing 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. Bob also appears in "Coming to Homerica", the 21st episode of season 20, in a joke in which the Simpson family enters the Cheers bar dressed as the Cheers cast and Sideshow Bob enters dressed as Frasier Crane.

In "O Brother, Where Bart Thou?" (season 21, 2009), Bob makes a non-speaking cameo appearance in Bart's dream sequence while the latter becomes desperate to have a younger brother. Cecil appears for the third time in The Simpsons alongside Bob; the brothers are flying kites together. Bob reappears in the episode "The Bob Next Door" (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 identity in his latest attempt to kill Bart, planning to use multiple state lines to evade prosecution, but he is foiled again and taken away by state police.

Bob 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 is one of many who express their desire for it to happen. He makes a silent appearance in "Moonshine River" (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" (season 25, 2014), he is revealed to be a chief scientist for a genetic engineering company named Monsarno, having received the position after he was selected as a 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 various historical figures' relics, which are stored in the Springfield Museum, to make himself a superhuman dictator. After being tempted into a murderous rage, he chases down Bart and Lisa and is about to kill them, but he is provoked into a fight, 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 gills he gave himself allow him to live.

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

In "Treehouse of Horror XXVI" (season 27, 2015), in the first segment called "Wanted: Dead, Then Alive", Bob uses Milhouse's phone to trap Bart in the band classroom and successfully kills him. At 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 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" (season 27, 2016), grunting in annoyance as he wipes Bart's graffiti off Hettie Mae Boggs' promo poster on the wall along with Snake Jailbird and other inmates.

Bob returns in "Treehouse of Horror XXVII" (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, 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" (season 28, 2016), Sideshow Bob appears in the background during the airport check-in scene in Cuba. Bob also makes a non-speaking cameo appearance in "The Nightmare After Krustmas" (season 28, 2016); as Krusty nearly drowns in a frozen lake, Bob stands among the crowd holding a sign that reads "Die Clown". He has a major role in "Gone Boy" (season 29, 2017), when he tries to locate Bart after he goes missing and is presumed dead. Bob finds Bart and prepares to kill him and Milhouse, but saves them at the last minute after recalling the prison therapist's lessons about moving on from his desire to kill Bart. The epilogue features an older Bob, now known as Elder Bob, being a lighthouse keeper and still regretting not having killed Bart.

In "The Fat Blue Line" (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" (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. In "I, Carumbus" (season 32, 2020), Bob makes a brief appearance as a Roman gladiator and is sliced in half by Obeseus (Homer). Later in the season in "Manger Things" (season 32, 2021), he appears on a Christmas card on which he is seen holding a wrapped-up Bart, with the text above him reading "Just what you've always wanted". Bob returns in a non-speaking cameo in "Meat Is Murder" (season 33, 2022), where he is seen signing the chests of citizens like Milhouse's father Kirk Van Houten at the celebration of Krusty Burger's 50th anniversary, a callback to the "Die Bart, Die" scene from "Cape Feare".

In the "Treehouse of Horror XXXIV" segment "Ei8ht" (season 35, 2023), in an alternative ending to "Cape Feare", Bob realizes that Bart is delaying his own death by making Bob sing Pinafore and, as a result, kills him, traumatizing Lisa. Thirty years later, the Springfield police ask 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 him. Lisa reveals 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 the season 36 episode "The Yellow Lotus", Bob has a supporting role, as he is shown to be married and in the same resort as the Simpsons. In the episode, Bob mentions that he has been diagnosed as a sociopath "with a slight touch of the narcissist" and is taking medication. When Marge tells Bob's wife about his previous deeds, she throws him off a cliff, only for Bob to survive and talk with Sideshow Mel.

Other media

Outside the television series, Bob is the main character of the 2024 Disney+ animated short film The Most Wonderful Time of the Year. Kelsey Grammer recorded several Sideshow Bob lines for The Simpsons Movie, but the scene was cut; the deleted scene shows him among the angry mob, intent on killing Bart until he learns that the mob is apparently after only Homer, prompting him to leave in disappointment. Sideshow Bob has appeared in Simpsons Comics, and 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" was later included on the album Go Simpsonic with The Simpsons, and the song "The Very Reason That I Live" from "The Great Louse Detective" was included on The Simpsons: Testify. A previously unaired song, "Hullaba Lula", originally written for "Day of the Jackanapes", was also included on that compilation. 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.

In The Simpsons Game, released in November 2007, Bob has a cameo appearance. Sideshow Bob appears in the 1991 The Simpsons Arcade Game in the fifth level, where he is pulling a cart containing a roast chicken health pickup. Bob was also included as a level boss in the 1991 video game Bart vs. the Space Mutants. 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.

In The Simpsons: Tapped Out, a city-building game released in February 2012, Sideshow Bob appears as a bonus character. Bob pops up every couple of hours, 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. This game event was split into three 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

Sideshow Bob first appeared in "The Telltale Head", the eighth episode of season 1. His design was relatively simple compared with the designs of later incarnations, and his hairstyle was rounded. However, towards the end of the episode, he appears again in a panning shot of a crowd, this time with his familiar hairstyle. His second appearance, and first major one, was 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 the character of Sideshow Bob sleeker and more refined to fit Grammer's voice technique. Following the redesign, animators tried to redraw his scenes in "The Telltale Head", but had insufficient time before the show was produced.

Bob has no lines of dialogue during the first half of "Krusty Gets Busted"; the character communicates only through 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. 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. 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".

Sideshow Bob's full name is Robert Underdunk Terwilliger. His last name is stated in "Black Widower", while his middle name is stated in "Sideshow Bob Roberts". 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 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 opponents they perceive as intellectually inferior. For "Black Widower", director David Silverman updated the character model to reflect Brad Bird's animation style. 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. 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". Bill Oakley and Josh Weinstein, the showrunners 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. Weinstein describes Bob's dialogue as difficult to write, due to his unique and refined style of speaking. Despite these challenges, the creators of The Simpsons usually look forward to "Sideshow Bob episodes"; the writers consider them enjoyable to write, and former director Dominic Polcino describes them as "a treat" to work on.

Kelsey Grammer initially expected Sideshow Bob to be a one-time role and calls him "the most popular character I've ever played". Grammer usually joins the show's "table readings" (wherein cast members read each script together for the first time), and former executive producer David Mirkin described working with Grammer as very pleasant, due to 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."

The show's writers admire Grammer's singing voice and try to include a song for each appearance. 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." Clausen composed Sideshow Bob's theme, which is played whenever Bob gets out of prison or is about to commit a sinister action and which was first used in "Cape Feare". It is based on Bernard Herrmann's score for the film Cape Fear. The musical score for "Cape Feare" earned Clausen an Emmy Award nomination for Outstanding Dramatic Underscore – Series in 1994.

Bob's prisoner number is often 24601, which is Jean Valjean's prisoner number in Les Misérables. Another of Bob's trademarks 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 iterations of the same joke in quick succession. The sequence has become known as the "rake joke" and was described by Entertainment Weekly as showing "genius in its repetitive stupidity".

Family

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 the brother of Grammer's character on Frasier. Cecil is voiced by David Hyde Pierce, who portrayed Frasier Crane's brother 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?" Several of Frasier 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. Many of the interactions between Bob and Cecil were based on those of Niles and Frasier. 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. 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 highbrow as Bob. 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 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".

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.

Kelsey Grammer's voice work has consistently received praise and has been described as "brilliant", "inimitable" 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 Weeklys 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."

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 and was placed third on Entertainment Weeklys 2003 list of the show's top 25 episodes. IGN considers it the best episode of the fifth season. In 2007, Vanity Fair called it the show's fourth-best episode because of its "masterful integration of filmic parody and a recurring character". 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, calling them Grammer's best roles. "The Italian Bob" and its writer John Frink won a Writers Guild of America Award in 2007 in the animation category. In December 2009, Robert Canning of IGN ranked the ten Bob episodes that had aired by then. Bob's first five episodes occupied the top five positions, with "Cape Feare" 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 "The Italian Bob" and the ninth-ranked "Funeral for a Fiend" were "the only ones I'd consider clunkers. These remaining episodes are all quite fun".

The character's line in "Sideshow Bob Roberts", "Attempted murder? Now honestly, what is that? Do they give a Nobel Prize for attempted chemistry?" was invoked in 2019 in what commentators called the "Sideshow Bob defense" of President Donald Trump during the Trump–Ukraine scandal.

Analysis

In Planet Simpson, author Chris Turner writes that Bob is written as a highbrow snob and conservative Republican so that the writers can continually use him as a straw man and pincushion. He represents high culture while Krusty represents low culture, and Bart, stuck in between, always wins out. 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 content of that show to present readings of classic literature and segments examining the emotional lives of preteens. He believes that by exposing the kids 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." He also tries to "manipulate the tastes of the masses" by becoming a criminal mastermind. 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 Machiavellian methods to acquire and maintain power.

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. Believing that "nobody who speaks German could be an evil man", they release him. 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 to fulfill Bart's last request. The tactic stalls Bob long enough for the police to arrest him.

References

Bibliography