Every Sideshow Bob Episode Of The Simpsons, Ranked Worst To Best
"Aaaah! Sideshow Bob!" Whenever Krusty the Clown's former sidekick "Rick rolls" Bart Simpson — showing up when least expected — the 10-year-old shrieks in terror. You can't blame the kid. Sideshow Bob has a vendetta against Bart. Bob constantly escapes from prison, attempts murder, and gets sent back to jail in an endless cycle.
Voiced by Kelsey Grammer, Sideshow Bob first appeared in 1990 during the first season of "The Simpsons." He's been a recurring bad guy (and occasional good guy) ever since. Whether he's eradicating television or holding office as mayor on two different continents, Sideshow Bob almost always has a scheme up his sleeves.
Throughout the nearly 750 episodes of "The Simpsons" that exist at the time of this writing, Sideshow Bob has been the focus of 16 of them. (He's shown up in silent or cameo appearances in a handful of additional episodes, but for brevity's sake, he's crucial to the main storyline of 16 of them.) How do Sideshow Bob's escapades stack up? How has the series' creative team adapted the character over the years? Let's take a trip through over three decades of animation history to discover every Sideshow Bob episode of "The Simpsons," ranked worst to best.
16. The Great Louse Detective (Season 14, Episode 6)
Most of Sideshow Bob's appearances follow the same basic structure: He escapes from jail, he plots to kill Bart, Bart outsmarts him, and Sideshow Bob goes back to jail. The repetitiveness is comical rather than lazy, with half the entertainment coming from knowing Bob will never succeed no matter how hard he tries — or will he?
This question is answered in the 2002 episode "The Great Louse Detective." Twelve years after Sideshow Bob's first appearance, the writers dare to answer what would happen if Sideshow Bob got his way. The efforts of an otherwise okay episode are eclipsed in its final moments when it breaks the story structure's cardinal rule.
Sideshow Bob does what many would consider "jumping the shark." He outwits Bart. He has the chance to kill his nemesis once and for all — and then chooses not to. It's a prime example of a TV story breaking its formula and never quite feeling the same thereafter (following in the footsteps of Phineas and Ferb discovering Perry's secret identity and Plankton finally stealing the Krabby Patty formula). The audience's intrigue lies in a question mark that's never answered. It feels off-kilter and devalues the structure when it's inevitably reinstated because the mystery is gone. Surprisingly, this isn't the only time the writers give Sideshow Bob his victory, but it is the first.
15. Gone Boy (Season 29, Episode 9)
Sideshow Bob's redemptive streak repeats with a second occurrence of letting Bart go when he has the opportunity to kill him. It's not that Sideshow Bob should kill Bart. It's that one of his funniest qualities is failing every time he tries to kill Bart. In this episode, seconds before a missile is about to blast Bart and Millhouse to smithereens, Sideshow Bob aborts the mission and sets the boys free.
The best part of this 2017 episode is when Bob believes Bart to already be dead. The news has reported the boy's alleged death. Bob laments that he wasn't the reason Bart died and goes to therapy to resolve these feelings. Later, despite Bob ultimately sparing Bart, we see a flash-forward to Bob's future. As an old man, he lives in a lighthouse and writes "Die Bart Die" in the sand every time the tide goes out. So even if he seems to have turned over a new leaf, viewers can rest easy knowing his change of heart apparently won't last.
14. Bobby, It's Cold Outside (Season 31, Episode 10)
The most recent major appearance of Sideshow Bob at the time of this writing might hint at the writers' future intentions with the character. Bob starts working as a seasonal Santa Claus at Santa's Village, an amusement park (which, according to its entrance sign, doubles as a "Bag-a-Reindeer" hunting range in the summer). When Bart encounters Bob as Santa, Bob promises he's not going to kill the boy. He's telling the truth. His job seems to have changed his heart.
This episode shines when it takes digs at holiday-themed pop culture. As Sideshow Bob watches "It's A Wonderful Life," and George Bailey yells at his daughter to stop endlessly tickling the ivories, Bob remarks, "That girl is pretty bad at the piano." Elsewhere, Bart proclaims, "I'm saving Christmas!" Bob retorts, "Every kid thinks they're doing that this time of year!" Meanwhile, at the Simpsons homestead, the family watches the "Fox News Yule Log," complete with the Bill of Rights and a photo of JFK, among other items, in flames.
The writers present a kinder Bob and dispose of the villainous personality the audience has known for decades. With this being the newest Sideshow Bob appearance to date, it's not a sure bet that his good side will prevail, but with two episodes in a row leaning that way, it's certainly a possibility.
13. The Man Who Grew Too Much (Season 25, Episode 13)
Sideshow Bob's appearance in this episode comes as a complete surprise, popping into the story seven minutes in. He's a paroled scientist at Monsarno Labs, volunteering his time to work with genetically modified foods. Bob's philanthropy is merely a cover for genetically modifying himself, ultimately attaining qualities of various creatures from the animal kingdom.
With the story leaning toward science, Lisa spends more time with Sideshow Bob than Bart. This difference brings a change of pace to the typical Sideshow Bob structure. Twenty-five seasons in, it's clear that the production crew isn't afraid to ask Kelsey Grammer to make ridiculous noises in his vocal performance. Having given himself a whale's sonar detection ability, Bob hilariously shrieks whale noises with abandon. Separate from the Bob storyline but providing plenty of laughs is a B plot, with Marge teaching a class about abstinence to teenagers. Her lessons go as gloriously tragic as you'd imagine.
12. Treehouse of Horror XXVI (Season 27, Episode 5)
Perhaps the only acceptable way for Sideshow Bob to ever win against Bart is in a "Treehouse of Horror" episode. These annual Halloween specials often show the characters in over-the-top stories with elements of sci-fi, horror, and fantasy. They don't follow the canon of the rest of the series and are often ridiculous by nature.
As is typical with these specials, "Treehouse of Horror XXVI" is split into three segments. The first, "Wanted: Dead, Then Alive," features Sideshow Bob killing Bart, then bringing him back to life, Frankenstein-style — only to kill him again. Bob repeats the process endlessly, forever wanting Bart dead but admitting the "spark" of their relationship is in the hunt. Sideshow Bob reflects on his quest of "24 years of trying to kill a 10-year-old child."
After killing Bart, Bob says, "I did what could not be done to Bugs Bunny by Elmer Fudd," acknowledging the trope of his character and inadvertently calling the bluff of his victory outside of any understood fantasy. The Elmer Fudd formula relies on his inability to kill Bugs. In the same way, if the writers were ever going to have Sideshow Bob kill Bart, a zany, non-sequitur "Treehouse of Horror" segment is the perfect platform to do so — even if it's unfortunate that the character breaks convention in the show's headcanon at various points.
11. Sideshow Bob's Last Gleaming (Season 7, Episode 9)
This spoof of movies like "Top Gun" is an on-the-nose, action-filled story of good guys vs. the baddie. In this case, though, that adversary isn't another nation. Sideshow Bob infiltrates an air show to declare he'll bomb the city if all television isn't canceled. (He's miffed that Krusty the Clown replaced him with a new assistant, Sideshow Mel.) The story has nods to Hollywood favorites throughout.
R. Lee Ermey from "Full Metal Jacket" guest stars in this episode as Colonel Hapablap, a no-nonsense soldier. Coincidentally, "Sideshow Bob's Last Gleaming" aired four days after the original "Toy Story" debuted in theaters in November 1995. Pixar's first movie features Ermey as the voice of Sarge, the leader of Andy's Green Army Man toys. It was quite a big week for Ermey to voice animated characters, huh?
In an eerie prediction of the future, the newscaster in this episode tells viewers that when television gets canceled, the audience can watch his "new program on PC World Nightly." The joke is a little more ambiguous than some of the other future events "The Simpsons" has allegedly predicted, but it's still spot-on in its assessment of the Internet overtaking television as the public's source of news. The episode concludes with a nonsensical, out-of-nowhere line from Grampa: "Come on, everybody! I'm gonna haul ass to Lollapalooza!" The family laughs and remarks, "Here we go again!"
10. Wedding For Disaster (Season 20, Episode 15)
It turns out that Marge and Homer never had a real wedding. They're fixing that, though, with a huge ceremony. However, it seems that mysterious someone with the initials "S.B." is trying to prevent the wedding from happening. Naturally, Sideshow Bob is the prime suspect. After all, Bart deduces, "He knows that if mom and dad never get married, I'll never be born!" It's a brilliant line from any of its equally comical angles.
"S.B." turns out to be Selma Bouvier, Marge's sister. Making Sideshow Bob a red herring is a refreshing change of pace that manages to keep the character authentic. Despite Bob not having as much screen time as in some of his other appearances, his presence is still essential to the story.
This episode also has its share of spiritual humor, both overt and subtle, that any viewer can appreciate regardless of their religious affiliation or lack thereof. The priest, for example, uses a smart device called a "Psalm Pilot." Elsewhere, when a scene cuts to a church service mid-sermon, the minister tells the crowd, "And so, in summary, there are only two real commandments."
9. Day of the Jackanapes (Season 12, Episode 13)
This madcap tale is Sideshow Bob's first appearance in four seasons, one of the longest stretches he's absent in the series. Upset that his show is being censored, Krusty the Clown decides to call it quits. "I think it's good for a show to go off the air before it becomes stale and repetitive," Marge remarks of the news (in the middle of the show's 12th season of its seemingly unending run on the air).
After escaping from prison yet again, Sideshow Bob becomes the PA announcer at Bart's school and intends to hypnotize Bart to kill Krusty during the clown's series finale. And what a finale it is! The writers ingeniously imagine what the show-within-a-show's last episode would be like if it were a real program. Among the best bits are "flashback clips" to Krusty's beginnings in the early days of television and Mr. Teeny the Monkey's inspired dance to the song "You Sexy Thing" by Hot Chocolate.
8. The Bob Next Door (Season 21, Episode 22)
This episode introduces an outlandishly funny plot point that ends up being a recurring joke in future episodes. In prison, Sideshow Bob switches faces with an inmate who's about to be released. Bob surgically removes his own face and replaces it with someone else's — a gag that's even better considering the inmate looks exactly like Bob, rendering the switcheroo altogether unnecessary.
Bob moves in as the Simpsons' new neighbor, and Bart is quick to catch on. Marge reassures him, "A lot of people sound like Sideshow Bob, like Frasier on 'Frasier.'" When the jig is up, a chase leads to an area of land where five different states converge. It's the New Jersey jurisdiction that takes Sideshow Bob back to the clink. "The Bob Next Door" is as solid an adventure as they come, with the face switch bringing a delightful new side to Sideshow Bob — as his skin constantly peels off his skull.
7. The Italian Bob (Season 17, Episode 8)
When the Simpsons take a trip to a village in Italy, they're shocked to discover Sideshow Bob is the mayor. We meet Sideshow Bob's new wife, Francesca, and toddler son, Gino. These new characters dimensionalize the longtime villain while retaining his essence as a bad guy 17 seasons into the series.
The episode fires on all cylinders from start to finish. As in any episode in which the family travels, Homer struggles to narrow his cultural divide. In a panicked moment, he shrieks in anguish, "Americano?! What the hell could that mean?" As Sideshow Bob considers uprooting his family, he spins a globe and blindly drops his finger on a random spot. It's Orlando, Florida. "Not in this lifetime!" he declares. Later, as the Simpsons fear Bob's wrath, they run into Krusty, who happens to be performing in an opera in Rome. They beg him not to let them be "the first Christians to die in the Colosseum."
The zingers keep coming, padded by the additions of Bob's new family. Though they don't stick around for every Sideshow Bob appearance from this point forward, they'll pop up now and then. Bob has taught Gino to hate Bart, teaching him a new word: "vendetta." The little tyke hysterically shouts it anytime he sees Bart. "Vendetta! Vendetta!" he yells in falsetto.
6. Sideshow Bob Roberts (Season 6, Episode 5)
After the host of a conservative radio show pressures Mayor Quimby to free Sideshow Bob from jail, Bob wins an election against Quimby. (Larry King serves as their debate moderator, naturally.) Soon, Bob is ousted when Bart and Lisa discover he counted dead people and pets as votes for himself.
While not containing any concrete predictions for the future, this episode oddly feels just as relevant today as it did when it aired in 1994. For starters, the script leans heavily on political humor with a level of universality that makes it just as relevant nearly 30 years later. Though our technology is different in the present day — we've mostly traded radio broadcasts for podcasts and influencers — the political pundits this episode parodies still influence voters in the modern age. In another example of the show predicting the future, one scene shows Homer reading an "Archie" comic book. He says to himself, "Stuck up Riverdale punks think they're too good for me," a phrase that takes on new meaning in an era when those same characters are "punkier" than ever in The CW's "Riverdale" drama series.
An especially quirky running gag in this episode involves Quimby vying for senior citizens' votes by promising them a "Matlock freeway," named after their favorite television show. When construction commences just outside the Simpsons' home, Homer panics. "It's the rapture!" he cries. "Quick! Get Bart out of the house before God comes!"
5. Black Widower (Season 3, Episode 21)
Sideshow Bob marries Aunt Selma in this early appearance that shows us his true villainy. For Bob, Selma is merely a means to an end — specifically, her end. Selma views their love as pure ("I need a man, and I cannot find one among the law-abiding"), but Bob tries to kill her by timing an explosion to coincide with Selma's habitual smoke break following every viewing of the TV show "MacGyver." (Whew, these storylines sound kinda wild out of context, eh?) Bart figures out the scheme before Bob does the deed, Selma is saved, and Bob goes back to jail.
As only the second episode in the series to feature Sideshow Bob in a starring role, the writers had a choice to make that would inform the character's presence going forward. Was Sideshow Bob's mustache-twirling nefariousness in his prior appearance a one-time thing, or could it serve as an entryway into the character going full-on villain? Of course, we all know the answer now, but at the time, the crew could have taken the character anywhere.
Anecdotally, this episode takes a jab at "Dinosaurs," the '90s live-action sitcom from the Jim Henson Company that featured the same family makeup as "The Simpsons." Each character's personality lined up almost identically to the famous family from Springfield. As Bart watches a TV show that's meant to resemble "Dinosaurs," he says, "It's like they saw our lives and put it right up onscreen."
4. Brother From Another Series (Season 8, Episode 16)
David Hyde Pierce (Kelsey Grammer's co-star from "Frasier") guest-stars as Sideshow Bob's brother, Cecil, in this story that gives insight into Bob's past. In a hysterical flashback, we learn that Cecil, not Bob, wanted to be Krusty the Clown's assistant. Cecil flopped his audition, while Bob unintentionally had Krusty in stitches with his genuinely outraged reaction to a pie in the face. The brothers' ongoing tension carries their relationship in this episode.
When two actors famously work together, and one of them later has a regular gig on a TV show, it's sometimes a tradition for the other actor to guest-star at some point. When John Stamos starred in his own sitcom, "Grandfathered," his former "Full House" co-stars Bob Saget and Dave Coulier guest-starred in separate episodes. Likewise, after Zac Efron and Ashley Tisdale filmed "High School Musical" together, Efron guest-starred on "The Suite Life of Zack and Cody" alongside series regular Tisdale.
Though "Frasier" was still in production when "The Simpsons" aired "Brother From Another Series," the tradition of two actors the audience knows from something else appearing together is nonetheless always a good time. Even though Bob is a stroke out of character, as he and Bart work together, he gets a pass for still being determinedly evil at heart, in this case, trying to thwart Cecil.
3. Funeral For a Fiend (Season 19, Episode 8)
At this point in the series (19 seasons in), Sideshow Bob has earned his legacy. In "Funeral For a Fiend," the writers craft a narrative worthy of that reputation with Sideshow Bob faking his own death. This episode is something of a celebration of the character, just as a real funeral would be. The story sees the return not only of Bob's brother, Cecil, but also of his wife, Francesca, and son, Gino. At the funeral, an armada of clowns endlessly piles out of one car. During the ceremony, Krusty sings a tribute to Bob that quickly strays into a melodic advertisement for a "Best of Krusty" DVD. Of course, it's all a ruse for Bob to execute one of his schemes. He winds up in jail yet again, this time with his family.
Aside from the pointed tributes to Sideshow Bob, the episode's first act involves the villain tricking the Simpsons into attending a Western-themed restaurant that doesn't actually exist. The baddie catches them by surprise when they enter the dining room, his reveal in each starring episode (and the Simpsons' subsequent cry of "Aaaah! Sideshow Bob!") having been established as something of a punchline. Even then, Homer still thinks the restaurant is real.
2. Cape Feare (Season 5, Episode 2)
Rich Moore directed this 1993 episode nearly two decades before helming "Zootopia" and both "Wreck-It Ralph" films for Disney. Adding to the talent roster, the episode aired during Conan O'Brien's tenure as "The Simpsons" producer. When Sideshow Bob escapes from prison and vows to kill Bart, the Simpsons move as part of the Witness Relocation Program. (Homer proudly wears a t-shirt that says "Witness Relocation Program.") Little do they know that Sideshow Bob has hitched a ride on the undercarriage of their car. Unfortunately for him, the family takes a few painful detours. ("Hey kids, wanna drive through that cactus patch?!")
Not only does this adventure feature Sideshow Bob in top form, but it also reveals the extremities of the villain's love of operetta. Bart bests Bob by begging him to sing the score from "H.M.S. Pinafore" by Gilbert and Sullivan, a perfect distraction.
"Cape Feare" opens with an amazing circus-themed couch gag. Later, as the kids watch Krusty's show, we see a hysterical clip from a hospital-themed "Itchy and Scratchy" sketch. Halfway through the episode, when the Simpsons relocate, the show resets and plays a redux of the series' theme song dubbed "The Thompsons," the family's new alias. These bits, paired with Homer's constant negligence of his son's heightened fear of Sideshow Bob attacking him at any moment ("BART, DO YOU WANT TO SEE MY NEW CHAINSAW AND HOCKEY MASK?!"), elevate the episode to hilarious heights.
1. Krusty Gets Busted (Season 1, Episode 12)
This 1990 misadventure was the first episode of "The Simpsons" to feature Sideshow Bob as a main player — and only the 12th episode ever of the series. Kelsey Grammer's debut as the voice of Sideshow Bob is also the villain's best appearance. Tired of being the brunt of Krusty the Clown's jokes, Sideshow Bob frames his boss with robbing Kwik-E-Mart. The crime and the ensuing mystery cement Bob's future as a recurring adversary for Bart, laying the foundation for his episodes' typical structure.
Amidst the turmoil, writers Jay Kogan and Wallace Wolodarsky pepper the script with hilarious dialogue. As Bart pulls the string of his Krusty toy, the clown doll shamelessly says, "Buy my cereal!" Later, Homer is held up at the scene of the Kwik-E-Mart crime, making him late for the family's visit with Marge's sisters to look at photos from their vacation. "You missed the entire slide show," Marge says when Homer finally arrives. "Oh, fantastic," Homer replies with sincerity.
Brad Bird directed "Krusty Gets Busted," infusing Sideshow Bob with the same dimensionality he later brought to "The Iron Giant," "The Incredibles," and "Ratatouille." As a subtle hint of Bird's involvement, Krusty's inmate number is A113. That's the number of the classroom where Bird and many other notable animation directors studied at the California Institute of the Arts. The number appears in every Pixar film.