-
(#1) Cape Feare
- Oct 07 1993
Sideshow Bob conjures Max Cady in this Cape Fear-inspired tale which finds Bart kidnaped by his greatest nemesis. Trapped on a houseboat, Bart uses his last request – for Sideshow Bob to regale him with a performance of the music from H.M.S. Pinafore – to buy some time. This episode is full of pop culture references while creating countless quotable moments amid a sea of suspense.
Fun fact: This episode was initially banned in Germany because it depicted a character in full SS gear.
-
(#2) Sideshow Bob's Last Gleaming
Enraged by the power TV shows like the Krusty the Klown Show have over viewers, Sideshow Bob escapes from prison, obtains a nuclear weapon, and demands that all broadcasts stop. Krusty defies the order, but Bob's bomb turns out to be a dud. Bob manages to kidnap Bart and embark on a kamikaze mission in an old Wright brothers plane which fails and Bob is arrested. It turns out, Krusty took one for the TV team and knocked it out of the park!
Fun fact: An alien briefly appears chilling out inside hangar 18, a nod to the famous Roswell crash in '47.
Original Airing: November 26, 1995
Season: The Simpsons - Season 7
Episode Number: 9 -
(#3) Brother from Another Series
- Feb 23 1997
This episode's title is inspired by the reunion of Kelsey Grammer (the voice of Sideshow Bob) and David Hyde Pierce (the voice of Cecil) who appeared as Frasier and Niles Crane, respectfully, on Frasier. Under the care of Cecil, Sideshow Bob appears to be a changed man, but Bart remains skeptical especially after finding a briefcase full of cash among Bob's possessions. In a surprising twist, it seems that Cecil is the evil brother – at least for a moment – before Bob gets himself in trouble for vowing revenge against Cecil.
Fun fact: The episode's title references the 1984 sci-fi drama The Brother From Another Planet while the episode itself includes a heavy dose of Fraiser references.
-
(#4) Sideshow Bob Roberts
- Oct 09 1994
Sideshow Bob has once again found his way out of prison and this time he wields his celebrity status to become the Mayor of Springfield. His new position makes it easy to upend the lives of the Simpsons, but Bart and Lisa – with a little help from Smithers – trick Bob into confessing to election fraud. It's All the President's Men meets A Few Good Men with a dash of Citizen Kane for good measure.
Fun fact: This episode marks the first appearance of Springfield’s Republican Party Headquarters. Perhaps non-ironically, it’s an old and scary castle.
-
(#5) Krusty Gets Busted
- Apr 29 1990
This is the episode that started Sideshow Bob's long quest for revenge against Bart Simpson who discovered that it was Bob, not Krusty, who robbed the Kwik-E-Mart. Kelsey Grammer made his first guest appearance with this episode, though the original script called for James Earl Jones to voice Bob.
Fun fact: This is the episode that spawned Bart's famous "I didn't do it" line, although it was Krusty who first said it.
-
(#6) Black Widower
- Apr 09 1992
Sideshow Bob and Bart's aunt Selma have struck up a romance. While everyone believes that Bob has changed his evil ways, Bart remains skeptical. Good thing for Bart as he foils a Bob's plot to kill Selma and take all her money. Of course, the episode ends with Bob swearing revenge on Bart. Psycho is referenced several times in the score and plot adding to the entertaining episode.
Fun fact: This episode marks the beginning of Patty and Selma's long love affair of all things MacGyver.
-
(#7) Day of the Jackanapes
- Feb 18 2001
Angered by Krusty's admission that he taped Judge Judy episodes over Krusty the Klown Show episodes featuring Sideshow Bob, Krusty's former sidekick vows revenge. Bob escapes from prison and finds work at Springfield Elementary where he hypnotizes Bart to carry out his bidding. Meanwhile, Krusty's new sidekick, Mr. Teeny, foils Bob's plan and, against all odds, Bob and Krusty reconcile. Too bad for Bob, the Springfield police weren't quite as forgiving.
Fun fact: This episode's plot parodies the 1962 political classic thriller The Manchurian Candidate.
-
(#8) The Great Louse Detective
- Dec 15 2002
Sideshow Bob acts as a guardian angel of sorts to Homer, who is being hunted by an unknown would-be-killer. After numerous attempts on Homer's life, Frank Grimes Jr – the son of Frank Grimes – is revealed to be Homer's enemy, as Grimes, Jr. blames Homer for his father's death. Once Homer is safe, Bob tries to kill Bart, but is unexpectedly stopped by his own conscience. It's a nice story that highlights the softer side of Sideshow Bob.
Fun fact: The plot takes its cues from The Silence of the Lambs, while the episode's title is a nod to the 1986 Disney film The Great Mouse Detective.
-
(#9) Treehouse of Horror XXVI
Sure, Treehouse of Horror episodes are traditionally non-canon, but this one still counts. Sideshow Bob finally gets revenge against Bart in the episode's first segment, "Wanted: Dead Than Alive." After finally killing Bart, Bob learns that hunting the perennial ten-year-old was the only thing that ever brought him joy. Bart gets reanimated and then seeks revenge on Bob completing the cycle of destiny. Even if Sideshow Bob is a villain, it was still somewhat satisfying to see him finally kill Bart, even if it didn't last.
Fun fact: This horror segment was inspired by the 1985 horror-comedy The Re-Animator, which, in turn, was inspired by one of H.P. Lovecraft's short stories.
Original Airing: October 25, 2015
Season: The Simpsons - Season 27
Episode Number: 5 -
(#10) The Italian Bob
- Dec 11 2005
The Simpsons travel to Italy to find that Sideshow Bob – now married with a son – has become the mayor of a small Tuscan village. No one in Italy knows about Bob's criminal past until Lisa, drunk on wine, reveals his secret. Bob gets fired as mayor and he and his family vow revenge on the Simpsons. Luckily, Krusty is performing in Italy and he sneaks the Simpsons back to Springfield.
Fun fact: This episode earned an Emmy Award for Outstanding Voice-Over Performance for Kelsey Grammer.
-
(#11) Funeral for a Friend
- Mar 20 1989
Sideshow Bob has reinvented himself yet again, this time as Wes Doobner, the owner of Wes Doobner's World Famous Family Style Rib Huts, a restaurant that lures the Simpson family into a devious trap that leads to Bob's arrest. Bob's trial is revealed to be yet another plot against the Simpsons and Lisa cracks the case before any member of her family is injured. John Mahoney voices Bob and Cecil's father, Dr. Robert Terwilliger, Sr., adding to more Frasier-inspired fun.
Fun fact: While the title was taken from an Elton John song of the same name, it could also be a reference to the Superman story arc where he was defeated by Doomsday.
-
(#12) Gone Boy
After falling in a manhole, Bart discovers an underground military bunker. Sideshow Bob – who is on a prison work assignment collecting trash – and others search for Bart, but the local news soon reports that Bart has passed. Eventually, Milhouse leads Sideshow Bob and after pushing Milhouse down the bunker, he ties them both to a deactivated missile. As he's about the press the lift-off button, Bob has a change of heart and later, back in prison, he engages in therapy. The episode also features a Christmas couch gag that is worth tuning in for.
Fun fact: A title twist spoofing the 2017 movie Gone Girl, this was also the first flash-forward Sideshow Bob episode.
Original Airing: December 10, 2017
Season: The Simpsons - Season 29
Episode Number: 9 -
(#13) The Man Who Grew Too Much
Lisa teams up with Sideshow Bob, now a scientist, to study the potential benefits of genetically modified foods. The pair bond over intellectual ideas and a shared love of literature, but Bob's hiding a secret: he's obtained a variety of special qualities because of genetically modified foods. Bob, of course, goes into a murderous rage, but Lisa, who is now joined by Bart, talks him down. While Bart is often duped by Sideshow Bob, it's fun to see Lisa with him for a change.
Fun fact: This episode was dedicated to Edna Krabappel's voiceover actress, Marcia Wallace.
Original Airing: March 9, 2014
Season: The Simpsons - Season 25
Episode Number: 13 -
(#14) The Bob Next Door
- May 16 2010
When the Simpsons get a new neighbor who sounds just like Sideshow Bob, Bart is suspicious. It turns out that he had good reason to be as Bob switched faces with his cellmate, Walt Warren, who was getting released from prison. It's almost too late when the real Walt reveals Bob's ruse, but Chief Wiggum and the other police officers save Bart in the nick of time. This episode features a fun reference to Kelsey Grammer's unique voice with Marge pointing out that Frasier on Cheers, Frasier on Frasier or Lt. Cmdr. Tom Dodge in Down Periscope all have voices just like Sideshow Bob.
Fun fact: This episode finally reveals Police Chief Clancy Wiggum's real age, which is 43. Hard to believe?
-
(#15) Bobby: It's Cold Outside
In one of the newer Bob-centered episodes, Sideshow Bob has a new job as a mall Santa, and his dedication to his newfound craft prevents him from causing Bart any harm. Bob and Bart end up joining forces to figure out who stole Lenny's Christmas gifts and discover that Mr. Burns and Smithers were behind the heist. Bob's performance as Santa warms Mr. Burn's heart and the presents are ultimately returned. Kelsey Grammer gets a chance to sing several times in the episode adding to the entertainment.
Fun fact: This episode is a direct sequel to "Gone Boy", making it one of only a handful of two-part episodes.
Original Airing: December 15, 2019
Season: The Simpsons - Season 31
Episode Number: 10
New Random Displays Display All By Ranking
About This Tool
Sideshow Bob is a fictional supporting character in the famous animated series The Simpsons. He was voiced by Casey Graham and made his first brief appearance in the first episode of the first season. According to the setting, Sideshow Bob graduated from Yale University, is also a Republican and champion of high culture, self-proclaimed as a genius.
Throughout the episodes, Sideshow Bob, the juggler, has never given up on revenge. As for the cause of the conflict, you will understand after watching this episode. The random tool lists 15 of the best episodes of The Simpsons about Sideshow Bob.
Our data comes from Ranker, If you want to participate in the ranking of items displayed on this page, please click here.