‘The Simpsons:’ The 12 Best Exploits of Sideshow Bob

This fall, he will reportedly kill Bart Simpson

Sideshow Bob on 'The Simpsons'

Almost 25 years ago, Sideshow Bob, Krusty the Clown’s reluctant sidekick decided to get revenge on his boss by framing him for an armed robbery.

Central to foiling his plot was one Bart Simpson, who put Sideshow Bob in jail instead.

Bob vowed revenge.


Last week, THE SIMPSONS producer Al Jean announced at the ATX Festival in Austin, Texas that Sideshow Bob will get that revenge in the 27th season’s Treehouse of Horror Halloween episode.

On many occasions, Sideshow Bob (voiced by Kelsey Grammer) would attempt to exact his revenge through murder, only to be foiled time and again.

Take a look back at 25 years of scheming and see how one of TV’s favorite recurring characters was born.

1.  BLACK WIDOWER (Season 3)
Bart: “Aunt Selma has one hour to live!”
Homer: “Hey, down in front!”

Sideshow Bob’s first appearance since framing Krusty came when he joined a prison dating service, meeting Selma Bouvier, one half of Marge’s unbearable sister team. In an attempt to inherit money she made in stocks, he tries to blow her up using natural gas, since she lost her sense of smell after a rocket flew up her nose as a child. Bart prevented the explosion and sent Bob back to prison.

Black Widower



2.  CAPE FEARE  (Season 5)
Homer Simpson: “Oh my God! Someone’s trying to kill me!! Oh, wait, it’s for Bart.” 

In the Simpsons’ spoof of horror films (especially CAPE FEAR), Bart receives a number of threatening letters written in blood (and one written in pen from Homer in response to Bart tattooing “Wide Load” on his butt). Bob tricks the prison parole board using higher cultured persona and is released. The Simpsons then join the witness protection program. Sideshow Bob follows them to their new houseboat and, as Bob attempts to kill Bart as the boat sails downriver, Bart asks that Bob sing the entire HMS Pinafore. The delay allows the police to find the boat and Bob ends up back in jail.


Sideshow Bob: No children have ever meddled with the Republican Party and lived to tell about it!

Sideshow Bob (aka Robert Terwilliger) is released from prison again, only to run for Mayor of Springfield as a Republican, defeating Democrat Joe Quimby. Despite a “Killing Bart Policy,” he makes life tough for the Simpsons, proposing the demolition of their house to build an expressway and sending Bart back to Kindergarten. In a hat tip to All the President’s Men, Bart and Lisa discover Bob rigged the election, which lands him in jail for the fourth time.

Bob Roberts

Mayor Quimby: “This town will not negotiate with terrorists. Is there a town nearby that will?”

Sideshow Bob kills TV in Springfield, threatening to blow up the city with a nuclear bomb unless all TV transmissions are stopped. Krusty hijacks the emergency broadcast system signal from a shack and after discovering the nuke is a dud, attempts to kamikaze Krusty’s shack with the Wright Brothers’ plane. The plane isn’t fast or heavy enough to make a dent, and Bob is captured.


Sideshow Bob: “Oh, I see. When it’s one of *my* schemes you can’t foil it fast enough, but when *Cecil* tries to kill you, ‘it’s hopeless, utterly, utterly hopeless.'”

This episode features Cecil, Bob’s brother (voiced by David Hyde Pierce of FRASIER). Bob joins a prison Christian outreach program and is released after being declared reformed by Reverend Lovejoy. He is discharged to the care of Cecil, who is running the construction of a dam. While trying to find dirt on Bob, Bart and Lisa discover Cecil is planning to sabotage the dam. And the three (yes, Bob, too) foil Cecil. Bob is sent back to prison with Cecil because, despite his innocence and a confession from Cecil, Chief Wiggum insists he was involved.

With Cecil



Sideshow Bob: The rake, my archenemy!
Bart: I thought I was your archenemy!
Sideshow Bob: I have a life outside of you, Bart

Bob discovers Krusty erased all the early shows featuring Sideshow Bob while Krusty declares retirement from television. Bob plans to kill Krusty at his retirement special using Bart in a suicide bomber vest. Bob overhears Krusty’s apology to Bob for turning him into a criminal and decides not to go through with the plan. Bob is sent to prison for attempted murder as Krusty thanks him again for the ratings boost.


Bart & Lisa: AAAHH!! Sideshow Bob!
Sideshow Bob: Oh, come now, we have been through so much together. Just call me Bob.
Bart & Lisa: AAAHH!! Bob!

Someone attempts to kill Homer, and despite the complaints of Bart and Lisa, Bob is released from prison to help find the would-be killer. Bob is hooked up to a electric shock device which allows the family to shock Bob anytime. Bob saves Homer’s life and then tries to murder Bart, but can’t bring himself to do it.

8.  THE ITALIAN BOB (Season 17)
Homer: Why can’t you people learn to speak my language? I learned to eat your food!

The Simpsons go off to Italy to retrieve a car for Mr. Burns. While there they run into Bob who has become the mayor of a small Italian town, and now ahs a wife and child. He allows them to stay on the condition that they don’t inform the people he used to be a criminal, so of course they do. Lisa gets drunk, outs Bob and after his citizens turn on him, both Bob and his wife swear a vendetta against the Simpsons.


9.  FUNERAL FOR A FIEND (Season 19)
Kent Brockman: “America has a tradition of turning outlaws into legends after their deaths: Billie the Kid. Bonnie and Clyde. Jesus Christ.”

Bob tricks the Simpsons into a fake rib joint, ties them up and attempts to blow them up using an overheating laptop and TNT. Lisa tricks Bob into picking up his laptop to check Shakespeare lines on Wikipedia and the computer explodes in his hands. Bob’s mother and father attend Bob’s funeral after he fakes his own death during the trial. He locks Bart in the coffin and attempts to cremate him while his family (including Cecil) looks on. The Simpsons blind Bob with unclaimed ashes and save Bart. The entire Terwilliger family, including his Italian wife and child are thrown in jail for 87 years.

Homer: “Reverend Lovejoy, you deliver pizza now? But we didn’t order any pizza. You forgot the pizza anyway. Marge, the pizza place screwed up again!”
Bob is suspected of kidnapping Homer to prevent him from attending his third wedding with Marge after they find a key with the initials “SB.” Since Bob has a solid alibi, he, Bart, and Lisa discover the real Homernapper, Selma Bouvier.

11.  THE BOB NEXT DOOR (Season 21)
Marge: “A lot of people sound like Sideshow Bob. Like Frasier on Cheers.”
Homer: “Or Frasier on Fraiser.”
Marge: “Or Lt. Cmdr. Tom Dodge in Down Periscope.”

Prison budget cuts find Springfield releasing all minor offenders, so Bob assumes the face and identity of his prison cellmate and moves next door to the Simpson family. He uses this position to kill Bart legally over state lines, but is taken in by State Police. He regains his face in a brief appearance in a later episode.


12.  THE MAN WHO GREW TOO MUCH (Season 25)
Lenny: I don’t get it. There are taboos about premarital sex in the Middle East, and you don’t see those people getting all violent.

Bob is the chief scientist for a genetic engineering company after having been a test subject, publishing the result of the experiments. Soon we find out Bob has altered himself to give himself superhuman abilities in a quest to make himself the ultimate dictator. After discovering the monster he’s become he attempts suicide from jumping off the Springfield Dam, but survives because of the gills he gave himself.




THE SIMPSONS airs Sundays at 8:00 PM on Fox.


Blake Stilwell

Blake Stilwell

Blake Stilwell is a writer and adventurer who loves television, film, and international relations. He is a former military combat photojournalist who has worked for ABC News, NBC Olympics, and HBO. Based in New York, often found elsewhere.
Blake Stilwell