Among its ever-growing cast of characters, The simpsons boasted a number of memorable villains over its many seasons, from guest stars to supporting cast. But perhaps no villain has become more beloved than Robert Terwilliger, known to many fans as Sideshow Bob.
Driven by vengeance to kill Bart after exposing him for framing Krusty the Clown, Sideshow Bob is megalomaniac and murderous but also erudite with a taste for the finer things, which somewhat ties Frasier Crane’s most famous role to his voice actor Kelsey Grammer. The combination of these factors led to Sideshow Bob having some very memorable lines.
Sideshow Bob’s Real Nemesis
“The rakes, my sworn enemy.”
A frequent running gag revolving around Sideshow Bob is a simple but comedic gag to accidentally step on a rake and get slammed in the face with. This is followed by an inaudible growl from Bob. The moment has become something iconic The Simpsons recurring moment and has been turned into numerous GIFs.
So it’s understandable that Sideshow Bob has a bubbling hatred for the garden tool, openly calling them his nemesis. Bart responds with “I thought I was your nemesis.” Bob then hilariously retorts with “I have a life outside of you, Bart.”
Admit your expertise
“Lisa, you don’t go ten years as a homicidal maniac without learning a few things about dynamite.”
Sideshow Bob is one of the most powerful characters in The simpsons due to the number of abilities and tricks up his sleeve, in addition to being intelligent and highly intellectual. One of those abilities is, in the style of stereotypical cartoon villains, an excellent knowledge of dynamite.
The fact that Lisa even asked the murderous villain about his knowledge of dynamite is funny. And of course, Sideshow Bob’s own admission of being “a murderous maniac” always falls well with fans and casual observers.
Bob flatters Selma
“Although kissing you would be like kissing a divine ashtray, that’s not what I had in mind.”
Marge’s older sister Selma has had her fair share of husbands, but her first and perhaps most memorable is Sideshow Bob. The two met through a pen pal scheme in prison and fell in love — or so Selma believed.
Selma introduces Bob to the Simpsons over dinner. Before proposing to her, Bob asks if he could do something “shocking” in front of his family, which Selma assumes is doing. Bob then falsely affectionately compares kissing Selma to a “divine ashtray”. The effect is both weirdly romantic and hilariously gross.
All villains need the perfect dialogue
“Wait! I got a good one now. Marge, say ‘Get away from my son’ again.”
Season 5 episode “Cape Feare” is considered one of the darkest episodes of The simpsons. A parody of the thriller starring Robert de Niro, the Simpsons are taken into federal custody, relocated, and given new identities after Sideshow Bob is released from prison. But that doesn’t stop Bob from almost succeeding in murdering Bart.
Yet true to The simpsons, the episode isn’t lacking in humor, such as when Bob actually asks Marge to repeat his creepy phrase after she comes up with her own nefarious response. It hilariously undermines the tone and highlights Bob as a supervillain at heart.
Literary references
“The biggest murder since Snape killed Dumbledore.”
Theatrical at heart, Sideshow Bob takes great pride in being a criminal mastermind and therefore prefers to carry out clever and well-planned plans. One such scheme was to kill Bart in the Five Corners, a point where five US states meet.
As a result, Bob gleefully calls it “the biggest murder since Snape killed Dumbledore”, which is, of course, referring to Harry Potter. Bart then complains “I haven’t gotten to that part yet!” Bob then looks at it in disbelief and comments, “It’s a four-year-old book.” This is a great quote for pop culture fans and makes it even funnier that Bart was unaware of a fact that even non-Potterheads know.
sibling rivalry
“Oh, I see! When it’s one of my schemes, you can’t outwit it fast enough! But when Cecil tries to kill you, it’s totally, totally hopeless!”
One of the best episodes of Sideshow Bob according to IMDb features his younger brother, Cecil. What makes the already brilliant chemistry between the two brothers even better is that Cecil is voiced by David Hyde Pierce, who plays Frasier’s younger brother, Niles.
There’s clearly sibling rivalry at hand when Cecil turns out to be the villain because Bob unwittingly stole his dream career of being Krusty’s sidekick. But this does not seem one-sided. When Lisa unsuccessfully admits defeat at the hands of Cecil, Bob explodes into the next hilarious rant.
self-aware irony
“By the way, I’m aware of the irony of appearing on TV to decry it, so don’t bother pointing it out.”
A great thing about The simpsons is his self-awareness in certain situations, and there’s a moment in one of Sideshow Bob’s schemes that’s a really confusing example.
One of his non-murderous schemes was to try to abolish television broadcasts in Springfield. He announces his criminal plan during an air show on, very ironically, a large television screen. The entire speech is pure melodramatic evil delivered in classic Sideshow Bob fashion, but fans can’t help but laugh at the irony. The irony is then fully and hilariously confirmed by Bob at the end of his monologue.
Bob is running for mayor
“Mayor Quimby even released Sideshow Bob – a man twice convicted of attempted murder. Can you trust a man like Mayor Quimby? Vote Sideshow Bob for mayor.”
We often make fun of politics in The simpsons and Sideshow Bob’s bid to run for mayor is no exception. Despite being a convicted felon, Sideshow Bob won the election, in part due to Quimby’s poor performance.
The Sideshow Bob still won despite casually and openly admitting his multiple beliefs is disconcerting, but a real stab at how corrupt politics can be. Mayor Quimby may not be the cleanest politician, but even he is a better choice than someone with murderous intentions.
Sideshow Bob’s first words
“My young friends. For years I have been silent except for the coarse glissandros of this primitive wind instrument.”
One thing most people don’t know about Sideshow Bob is that before he became a notorious criminal, he worked for Krusty the Clown. Not much is seen of Bob’s TV career, but he is featured in “Krusty Gets Busted,” the iconic episode that began his quest for revenge against Bart.
This quote is Sideshow Bob’s very first line, both on TV after Krusty is sent to prison, and throughout the series. It’s an immediate introduction to his theatrical, high-class, well-spoken personality.
Sideshow Bob’s tagline
“Hello Bart.”
It’s a well-known fact that every main character in The Simpsons has a catchphrase. And without a doubt, Sideshow Bob’s catchphrase is “Hello, Bart.”
How two simple words can send shivers down the spines of many viewers is a fantastic achievement. It really cements just how perfect Grammer is at voicing the evil yet erudite former TV star, making what should be a feared character a beloved one.
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