Random Best Sideshow Bob Episodes Of 'The Simpsons' (15 items)

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  (#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.
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  (#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.
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  (#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.
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  (#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.
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  (#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.
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  (#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

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