Among its ever-growing cast of characters, The Simpsons has boasted a number of memorable villains across its many seasons, be they guest stars or supporting cast. But perhaps no villain has become more beloved than Robert Terwilliger, known to many fans as Sideshow Bob.

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Driven by revenge to kill Bart after he exposed him for framing Krusty the Clown, Sideshow Bob is megalomaniacal and murderous yet also erudite with a taste for the finer things, which somewhat links his voice actor Kelsey Grammer's most renowned role of Frasier Crane. The combination of these factors has led to Sideshow Bob having some very memorable lines.

Sideshow Bob's Real Arch Nemesis

"Rakes, My Arch Enemy."

Sideshow Bob gets hit by a rake

A frequent running gag revolving around Sideshow Bob is a simple yet comically slapstick gag of accidentally stepping onto a rake and getting smacked in the face with it. This is followed by an inaudible grumble from Bob. The moment has become something of an iconic Simpsons recurring moment and has been made into many a GIF.

So understandably, Sideshow Bob has a seething hatred for the garden tool, openly calling them his arch-nemesis. Bart replies with "I thought I was your archenemy." Bob then hilariously retorts with "I have a life outside of you, Bart."

Admitting His Expertise

"Lisa, You Don't Spend Ten Years As A Homicidal Maniac Without Learning A Few Things About Dynamite."

Sideshow Bob holds up Lisa and Bart in The Simpsons

Sideshow Bob is one of the most overpowered characters in The Simpsons due to the number of abilities and tricks up his sleeve, as well as being clever and highly intellectual. One of these abilities is, in true stereotypical cartoon villain fashion, excellent knowledge of dynamite.

The fact that Lisa even questioned the murderous villain on his dynamite knowledge is amusing. And of course, Sideshow Bob's own admittance to being "a homicidal maniac" always lands well with both fans and casual watchers alike.

Bob Flatters Selma

"Although Kissing You Would Be Like Kissing Some Divine Ashtray, That's Not What I Had In Mind."

Sideshow Bob massages Selma's feet in The Simpsons

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 prison pen pal scheme and fell in love — or so Selma believed.

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Selma introduces Bob to the Simpsons over dinner. Before he proposes to her, Bob asks if he could do something "shocking" in front of her family, which Selma assumes making out. Bob then faux-affectionately compares kissing Selma to a "divine ashtray." The effect is both oddly romantic and hilariously disgusting.

All Villains Need The Perfect Dialogue

"Wait! I've Got A Good One Now. Marge, Say 'Stay Away From My Son' Again."

Sideshow Bob in Cape Feare - The Simpsons

The season 5 episode "Cape Feare" is considered one of the darkest episodes of The SimpsonsA parody of the thriller starring Robert de Niro, the Simpsons are placed under federal protection, relocated, and given new identities after Sideshow Bob is released from prison. But that does not stop Bob from almost succeeding in murdering Bart.

Yet true to The Simpsons, the episode isn't short of humor, such as when Bob actually asks Marge to repeat her fearful line after coming up with a good nefarious response of his own. It hilariously undercuts the tone and highlights Bob as a supervillain at heart.

Literary References

"The Greatest Murder Since Snape Killed Dumbledore."

Sideshow Bob, Lisa and Bart from The Simpsons

Theatrical at heart, Sideshow Bob takes great pride in being a criminal mastermind and thus prefers to fulfill intelligent and well-planned schemes. One such scheme was to kill Bart in the Five Corners, a point where five US states meet.

As a result, Bob gloatingly calls it "the greatest murder since Snape killed Dumbledore," which is a reference, of course, to Harry PotterBart then complains "I haven't got to that part yet!" Bob then looks at him in disbelief and comments, "It's a four-year-old book." It's a great quote for pop culture fans and made even funnier for how Bart wasn't aware of a fact that even non-Potterheads know.

Sibling Rivalry

"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 Utterly, Utterly Hopeless!"

Sideshow Bob and his brother Cecil in The Simpsons

One of the best Sideshow Bob episodes according to IMDb introduces 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 is clear sibling rivalry at hand when Cecil reveals himself to be the villain because Bob unintentionally stole his dream career of being Krusty's sidekick. But this appears to not be one-sided. When Lisa futilely admits defeat at Cecil's hands, Bob explodes in the following hilarious rant.

Self-Aware Irony

"By The Way, I'm Aware Of The Irony Of Appearing On TV In Order To Decry It, So Don't Bother Pointing That Out."

Sideshow Bob on a giant TV from The Simpsons

One great thing about The Simpsons is its self-awareness in certain situations, and there is one moment in one of Sideshow Bob's schemes that is a really side-splitting example.

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One of his non-murderous schemes involved trying to abolish television shows in Springfield. He announces his criminal plan at 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 cannot help but chuckle at the irony. The irony is then fully and hilariously confirmed by Bob at the end of his monologue.

Bob Runs 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."

Sideshow Bob and Mayor Quimby run for mayor from The Simpsons

Politics are frequently made fun of in The Simpsons and Sideshow Bob's bid to run for mayor is no exception. Despite the fact that he is a convicted criminal, Sideshow Bob won the election, partially thanks to Quimby's poor performance.

The Sideshow Bob still won despite having casually and openly admitted to his multiple convictions is baffling, yet 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 Save For The Crude Glissandros Of This Primitive Wind Instrument."

Krusty and Sideshow Bob in The Simpsons

One thing that 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 introduced in "Krusty Gets Busted," the iconic episode that started his quest for revenge against Bart.

This quote is Sideshow Bob's first-ever line, both on the television after Krusty is sent to prison, and in the series overall. It is an immediate introduction to his theatrical, high-class, and well-spoken personality.

Sideshow Bob's Signature Catchphrase

"Hello, Bart."

Sideshow Bob and Bart in The Simpsons Treehouse of Horror XXVI

It is a well-known fact that all main Simpsons characters have a catchphrase. And without question, Sideshow Bob's catchphrase is "Hello, Bart."

How two simple words can send shivers up the spines of many a viewer is a fantastic achievement. It truly cements just how perfect Grammer is at voicing the evil yet erudite former television star, making what should be a feared character a beloved one.

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