My Top Five Favorite Sideshow Bob Episodes

 

While Mr. Burns is undoubtedly the most evil character on "The Simpsons", the silver medal would definitely go to Robert "Sideshow Bob" Terwilliger (who has sinister theme music to boot). Throughout the show's run, Sideshow Bob's appearances are generally enjoyable episodes, thanks in part to the performance of his voice actor, Kelsey Grammer, who perfectly captures the eloquent psychopathy of the character. As Sideshow Bob stories tend to have higher stakes than a traditional episode (and more often than not involve him trying to kill Bart), I thought that for this Halloween, I'd share my thoughts on some of the character's best ventures. These are my top five favorite Sideshow Bob episodes (and keep in mind, there will be spoilers).

5. THE BOB NEXT DOOR (21.22)

PREMISE: Bart becomes convinced that their new neighbor is Sideshow Bob in disguise.
WHY IT MAKES THE LIST: This is a unique Sideshow Bob episode and it does a good job in making you wonder if the Simpsons' new neighbor, Walt Warren, really is Sideshow Bob and how he's pulling it off. Despite his voice being similar and Bart's attempts to prove it, seeing Sideshow Bob still locked away in prison seems to settle the matter. In the big reveal though, it turns out Walt was Bob's former cellmate and was set for early release, which prompted Bob to go all Nicolas Cage on him. Yes, this episode is inspired by the movie "Face/Off", and in turn, I think this episode may have inspired the Joker ripping his own face off in "Batman: Death of the Family". In any case, Bart not being fully convinced does lead to Bob being imprisoned again and getting his own face back; though apparently whoever grafted it back on didn't do a good job because there's a new running gag in subsequent Sideshow Bob episodes where Bob's face peels off and has to be pressed back on.

4. THE GREAT LOUSE DETECTIVE (14.6)

PREMISE: With Homer targeted for murder, Chief Wiggum recruits Sideshow Bob to help find the mystery assailant.
WHY IT MAKES THE LIST: While not the first Sideshow Bob episode where he's not featured as the main antagonist, this episode is unique in having Bob from the get-go be an ally to the Simpsons, albeit a reluctant one (he's offered his choice of role for the prison musical in exchange for his help). To keep Bob in check, he does have a collar around his leg that gives him a shock from a remote control, which makes up most of Bob's comedic moments in the episode. The really entertaining part though is the extended interaction between Homer and Bob, who tries to understand and endure the person he's charged with saving. As Bob was brought in so they could understand the mind of a killer, this does pay off with Bob putting together the clues and figuring out the killer's identity, effectively making him the hero of the episode (a rare occurrence to be sure). I won't reveal the killer's identity here, but it does tie in with another classic Simpsons episode.

3. FUNERAL FOR A FIEND (19.8)

PREMISE: Sideshow Bob's latest scheme leads to his apparent death at Bart's hand.
WHY IT MAKES THE LIST: While the episode feels like a typical Sideshow Bob story for the first half, the second half is what really stands out to me because I feel this was intended to be the character's final episode. Though Bob's death is obviously a ruse and part of his plan, if successful, it would have been his ultimate revenge against Bart. Before faking his death, Bob had been able to flip the script at his trial by painting himself as the victim of Bart's persecution, which was easy to do given Bart's penchant as a hellraiser. The episode also features the debut of Bob's parents, the return of his brother Cecil (voiced once again by David Hyde Pierce), as well as his wife Francesca and their son Gino. The whole family is part of the plan, which a keen eye will pick up this was hinted at earlier in the episode during Bob's big return moment; as such, it's fitting the whole family is locked away together by the end of the episode. Lisa putting the pieces of the Terwilligers' plan also felt like a callback to the first two Sideshow Bob episodes. With the nature of the plan, return of past characters and callbacks to previous episodes, I feel this is the pique Sideshow Bob story and would have served as a decent farewell to the character. I kind of wish it was too as I feel that Sideshow Bob episodes since this one (with the exception of "Bob Next Door") don't have the same magic as what came before. Honestly though, it also just feels odd how Bob has seemingly abandoned his family (particularly his wife and son) since this episode, apparently due to him being unable to let go of his obsession with Bart. Being a family man really added a new layer to the character in my opinion, and I do hope a future Sideshow Bob episodes allows us to check in on Francesca and Gino.

2. BLACK WIDOWER (3.21)

PREMISE: Selma reveals that she has a new boyfriend that she met through the prison pen-pal program, Sideshow Bob.
WHY IT MAKES THE LIST: For the direct sequel to "Krusty Gets Busted", Kelsey Grammer's debut episode as Sideshow Bob, it would have been easy for the creators to do a story right away where Bob goes after Bart for putting him in jail. Having Bob's second episode subvert expectations was a genius move, showing his relationship with Selma help reform him...or so it seemed. The first two acts of the episode do a good job showing what happened to Bob since his first episode and how well he can play a good guy and win everyone over. Well, everyone except Bart who never lets go of his mistrust of the man who framed his hero. That mistrust pays off though as Bart is able to piece together Bob's deadly intentions with Selma (which also shows Bart can be a deep thinker when he applies himself). If I had a small criticism though, it's that episode's third act makes it clear Bob intends to kill Selma where I think it would have helped keep that hidden until Bart realizes it, revealing all the clues in the episode's conclusion. And for what it's worth, I think Bob did initially have real feelings for Selma, but learning how much money she has in stocks seemed more appealing to him and started to plan. Framing Krusty for years of humiliation or plotting revenge on the one who put you in prison is one thing, but planning to kill someone he apparently loved for money showed how much of a sociopath the character truly was even in his earliest appearances.

And my number one Sideshow Bob episode is...

CAPE FEARE (5.2)

PREMISE: The Simpsons enter witness protection when Sideshow Bob threatens Bart's life.
WHY IT MAKES THE LIST: For his third ever appearance where he finally goes straight for revenge on Bart, "Cape Feare" highlights everything fans love about Sideshow Bob. There are three main aspects of Bob that make him such a memorable character and they're all present in this episode. The first is his menace, which is shown prominently in his psychological torture of Bart both before and after his release from prison. But that menace is rightly balanced with his moments of comedic ineptitude. While Sideshow Bob is not to be taken lightly, it's the times where he makes a fool of himself that make him relatable and not too cartoonishly evil. Whether it's asking for a do-over after thinking of a better comeback to a comment from Marge or suffering physical abuse like being stepped on by a parade of elephants and taking multiple rake handles to the face, this episode does a good job at making you laugh at someone who's literally planning to kill a child. Aside from bringing the fears and funnies though, the aspect of Sideshow Bob that's probably most important to him is his showmanship. Not only is Kelsey Grammer a great voice actor, but he's also a great singer as the episode puts on full display in the climax. In order to buy himself time, Bart asks Sideshow Bob to sing the entire score of "HMS Pinafore" for a last request. In the snippets they show of Bob's performance, you can tell Grammer really gave it his all. In summation, "Cape Feare" is probably the perfect Sideshow Bob episode, striking the right balance of chills and laughs with an exceptional performance from Kelsey Grammer.