In Simpsons Season 27 Sideshow Bob Finally Kills Bart

Plus: Sideshow Bob Trivia

After over 25 years of obsessive conniving and failed assassination attempts, original Simpsons’ baddie Sideshow Bob will finally kill Bart. This is not a late April Fools’ Day prank or an internet hoax. Series producers revealed the news during their ATX Festival panel in Austin, Texas, on Saturday.

According to a report in Entertainment Weekly: Executive producer Al Jean said he always wanted to see the Coyote get the Road Runner in the classic Looney Tunes cartoons. “I hated frustration comedy so we’ll scratch that itch,” Jean told EW. So Bob will finally somehow actually execute Bart—and then won’t know what to do with himself after his life’s mission has been accomplished.



Sideshow Bob, born Robert “Bob” Underdunk Terwilliger, Jr., (voiced by Kelsey Grammer), known for his outlandish red afro and humongous feet, has a long and sordid history with the Simpson clan; it all started back in Season 1 when Bart foiled his plans to frame Krusty for armed robbery. After a brief stint in prison, Bart unraveled another one of Bob’s dastardly plots (in Season 3) when he prevented the con from blowing up his Aunt Selma. Returned to prison for a second time, Bob became obsessed with murdering Bart Simpson.

Since then, Bob has perused the Simpsons when they entered the Witness Protection Program (in a brilliant nod to 1991’s Cape Fear), rigged an election to become Mayor of Springfield, attempted to blow up the entire town, went straight before being pulled back into a life of crime by his brother, became Mayor of a town in Italy, faked his death, underwent painful plastic surgery, and used GMO’s to alter his DNA—all in an attempt to kill a specific spiky-haired 10-year-old.


Simpsons Renewed Through Season 28

So if Bart’s getting killed in Season 27, and The Simpsons has been renewed through Season 28, does that mean our favorite yellow family will be one member lighter as it moves forward? Of course not! I mean, can you imagine? It wouldn’t be the first time producers have offed a character (most shockingly, Maude Flanders) but who really believes they’re going to assassinate a child (not to mention the most popular character besides Homer, hands down)? So what then? Dream sequence? Parallel universe? The deed undone through time travel? Even better: Treehouse of Horror XXVII!

Once a year, The Simpsons breaks format for a 3-part Halloween episodes where the legal and physical laws that govern Springfield hold no sway. So whatever happens to Bart in October, we can rest assured he’ll be back with slingshot in his pocket in November.


At the ATX Fest, Al Jean revealed that Bob will kill Bart, and then suddenly not know what to do with himself now that his life’s goal has been actualized. I can see this set-up leading into several great horror parodies; for example: A devastated Bob buries Bart in “sour ground” ala Louis Creed from Pet Sematary. Or what about: Bob injecting Bart’s severed head with a syringe filled with a neon chemical cocktail like Herbert West in Stuart Gordon’s Re-Animator (1985). They could even keep it classic with a reimagining of Shelley’s Frankenstein, or Bob could enter into a good old fashioned deal with the Devil. Hey Simpsons writers: Feel free to use any of these ideas—I promise not to sue you!

Sideshow Bob Trivia.


Did you know:

  • The script for “Krusty Gets Busted” called for Sideshow Bob to be voiced by James Earl Jones (Mr. Darth Vader himself) but producers went with Kelsey Grammer instead. Since Bob didn’t speak for the first half of the episode (merely tooting a slide-whistle) it was a shock to finally hear Grammer’s sophisticated baritone.
  • Despite the common fan belief that Bob is named after Terwilliger Blvd. in Portland, Oregon, he’s actually named after the character Dr. Terwilliger from the movie The 5,000 Fingers of Dr. T.
  • Despite being written as a one-time character, Sideshow Bob has been featured heavily in 10 episodes of The Simpsons.
  • Kelsey Grammer calls Sideshow Bob “”the most popular character I’ve ever played.”
  • Grammer recorded Sideshow Bob dialogue for The Simpson’s Movie, but his scene was cut and never animated.
  • In many ways, Sideshow Bob is modeled after Hannibal Lecter: He’s the kind of villain who can recite Shakespeare while stabbing you in the face!
  • In 2006, Sideshow Bob ranked 2nd on’s “Top 25 Simpsons Peripheral Characters” list.
  • Sideshow Bob is the most tattooed character in the Simpson’s universe, sporting the following ink: “Die Bart, Die” on his chest, Bart’s decapitated head on a skateboard with a speech-bubble saying, “Ouch, Man!” on his back, “LUV” on his right knuckles & “HāT” on his left knuckles, a skull & crossbones on his upper left arm, and a knife on his upper right arm.
  • Producers always strive to give Bob a song to sing. Check out his wicked Pagliacci below.

How would you like to see Sideshow Bob finally get his revenge on Bart? Sound off in the Comments section!

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  • Matthew Myers
    11 June 2015 at 11:22 pm - Reply

    Great article! I have been waiting to see this for a long time.