The Simpsons is among the longest running American sitcoms in history. Clocking in at 750 episodes—with no sign of slowing down—the cartoon must remain inventive to keep viewers engaged.
One way to do that? Anthology episodes that follow certain themes, characters, or storylines—such as the "Treehouse of Horror" episodes, the "Clip Show" compilations, or the episodes that center on Sideshow Bob (a.k.a. Robert Underdunk Terwilliger).
A well-spoken genius villain whose ego always lets him down, Sideshow Bob also happens to be Bart's archenemy. A homicidal maniac with a passion for art, Sideshow Bob boasts wild red hair and curiously speaks with a Transatlantic accent.
We first met Sideshow Bob in "The Telltale Head" (Season 1 Episode 8), but his first spotlight appearance came in "Krusty Gets Busted" (season 1 Episode 12). Since then, he's appeared in over 40 episodes.
Here are my picks for the best episodes of The Simpsons featuring Sideshow Bob and why they're so good!
8. The Great Louse Detective (Season 14 Episode 6)
In "The Great Louse Detective," Sideshow Bob is hired to investigate the failed murder of Homer Simpson, parodying Jonathan Demme's classic film The Silence of the Lambs.
With Sideshow Bob being an avid singer who would fit better in an opera house than a Springfield prison, we even get one of his little musical treats at the end of this episode.
It's far from the first time The Simpsons moved the focus of a Sideshow Bob episode away from Bart, but this episode occurs at the tail end of The Simpsons's heyday (in what many consider to be the last season that remains watchable by the skin of the show's teeth).
Sideshow Bob is the protagonist in a handful of episodes after season 14, but by that point his purpose is a little worn out.
7. Day of the Jackanapes (Season 12 Episode 13)
If there's one thing The Simpsons has never been short on, it's guest appearances. Gary Coleman cameoed in seven episodes (plus the love-it-or-hate-it movie spin-off) before his untimely death in 2010, and one of those episodes was "Day of the Jackanapes."
Krusty the Clown is always getting his show canceled for one reason or another. This time, it's due to the heavy competition from another new game show called Me Wantee!
Announcing his retirement, Krusty admits to taping over all of his old episodes featuring Sideshow Bob, which—unsurprisingly—sends Bob into a murderous rage.
Next to Bart, it's Krusty who's continually the victim to Sideshow Bob's schemes, which makes sense since Robert Terwilliger got his nickname from being Krusty's original sideman.
6. Brother From Another Series (Season 8 Episode 16)
You might recognize Sideshow Bob's voice from the hit 90s sitcom Frasier, which starred Kelsey Grammer.
The Simpsons loves to make pop culture references, and in "Brother From Another Series" we get a direct nod to Grammer's most famous role—through the title card that reads: "FRASIER IS A HIT SHOW ON THE NBC TELEVISION NETWORK."
Of course, there's also the general reference that Sideshow Bob's uptight sophistication is itself a parody of the Frasier character!
This episode inverts the usual Sideshow Bob narrative, as this time around he actually saves Bart. But from whom? It turns out that Bob has a younger brother, Cecil—and who else to voice him except Frasier's own brother, played by David Hyde Pierce.
5. Sideshow Bob Roberts (Season 6 Episode 5)
Nothing is safe from the mockery of The Simpsons, including its own broadcasting company Fox Network. In "Sideshow Bob Roberts," the Republican party is the butt of the sitcom's main jokes.
In Springfield, the right-wingers are made up of the obese and anti-politically correct radio host Birch Barlow, Richard "Rich Texan," Mr. Burns, Dracula, and their latest recruit, Sideshow Bob. Basically, all the terrible people in the town.
But don't worry! In order to remain neutral, the episode throws in a few punches at the Democrats, too.
Recently released from prison, Sideshow Bob runs for Mayor and wins. And, as usual, his plot is foiled by Bart and Lisa, who land him on trial for electoral fraud.
4. Sideshow Bob's Last Gleaming (Season 7 Episode 9)
Is there no one else around to stop Sideshow Bob from killing people besides the two Simpson kids?
Well, in "Sideshow Bob's Last Gleaming," Bob doesn't just target Bart—he targets all of Springfield. (We've lost count of how many times Springfield has been on the brink of destruction.)
In this episode, the town's residents are innocently enjoying an air show when Sideshow Bob appears on the big screen to threaten nuclear destruction.
Even though he was once a clown's sidekick, Sideshow Bob's signature trait is his upper-class, snobby taste in art and culture. So, now he seeks to get even by forcing Springfield to tune out TV's "mindless drivel."
3. Black Widower (Season 3 Episode 21)
Marge's hateful, chain-smoking, MacGyver-obsessed sister Selma seems like the last person Sideshow Bob would go for. And, as it turns out, that's completely right!
He's only using her to get out of prison and inherit her stock market fortunes—after killing her, of course. Luckily, Bart's skepticism at Sideshow Bob's reformation is what saves the day.
"Black Widower" is one of the earlier episodes to revolve around Sideshow Bob, and as is usually the case with The Simpsons, "earlier episode" typically means "better."
2. Cape Feare (Season 5 Episode 2)
You'd be hard-pressed to find an episode of The Simpsons that doesn't reference a movie. But some references are more heavy-handed than others, like when an entire episode spoofs a film.
Such is the case with "Cape Feare," which spoofs both the 1962 and 1991 versions of the psychological thriller Cape Fear.
The Simpsons's use of other movies as templates can sometimes feel lazy, but in "Cape Feare," it's done as a clever parody with the perfect balance of original scenes and movie nods. (This is also the episode that coined Sideshow Bob's iconic "Die Bart, Die" line.)
Robert De Niro laughing in the cinema with his cigar and Hawaiian shirt is echoed by Sideshow Bob, whose name is likely what inspired the link to Cape Fear. (However, once we've wound up on the boat, The Simpsons gives us a musical grand finale instead.)
1. Krusty Gets Busted (Season 1, Episode 12)
Ah, here's the episode that started it all. "Krusty Gets Busted" is the penultimate episode of season one, so a lot was riding on it to earn the green light for a second season. The fact that we got 33 more seasons (so far) says everything about how good it is!
Sideshow Bob's first dedicated episode sees him in his original, shirtless, pie-covered form, getting fired out of a cannon, which adds to his teeming resentment for Krusty.
But when Krusty is sent to jail for robbing the Kwik-E-Mart, Sideshow Bob takes over the kids show and revamps it with classic literature and nutritional education.
"Krusty Gets Busted" also set the foundation for Sideshow Bob's vendetta against Bart, who discovers that Krusty was actually framed by Sideshow Bob. (All with the help of Lisa, back when they were a cute detective duo and not feuding sibling rivals!)
For all these reasons, "Krusty Gets Busted" will always be our favorite episode of The Simpsons to feature Sideshow Bob.