Ashely Puckett

Ashely Puckett

Modified & Updated: 09 Sep 2023


Sideshow Bob, the iconic character from the long-running animated show “The Simpsons,” has captivated audiences with his distinctive voice, devious schemes, and hilarious antics. Voiced by Kelsey Grammer, this recurring character has become a fan favorite for both his comical misadventures and his villainous persona.

In this article, we will dive into 24 fascinating facts about Sideshow Bob that every fan should know. From his memorable appearances to his remarkable voice acting, we will explore the behind-the-scenes details that make Sideshow Bob an unforgettable character in the world of cartoons. So get ready to delve into the intriguing world of Sideshow Bob and discover some surprising tidbits about this beloved character.

Table of Contents

Sideshow Bob is a recurring character in “The Simpsons”.

Sideshow Bob, originally known as Robert Underdunk Terwilliger, is one of the most memorable and cunning characters in “The Simpsons”. He first appeared in the episode titled “The Telltale Head” in Season 1.

Sideshow Bob is voiced by Kelsey Grammer.

Kelsey Grammer, who is widely recognized for his role as Dr. Frasier Crane in the hit sitcom “Frasier”, provides the distinctive voice of Sideshow Bob. His voice acting talent brings the character to life and adds depth to his villainous persona.

Sideshow Bob’s original job was to be Krusty the Clown’s sidekick.

Prior to his turn as a criminal mastermind, Sideshow Bob was intended to be Krusty the Clown’s loyal and trusted sidekick. However, due to unforeseen circumstances, Bob’s character took a more treacherous path, becoming one of the Simpson family’s most formidable foes.

Sideshow Bob’s hair resembles a palm tree.

One of the most distinctive features of Sideshow Bob is his unique hairstyle. With a towering, curly red afro that resembles a palm tree, his hair is certainly an eye-catching attribute that sets him apart from other characters in the show.

Sideshow Bob’s biggest vendetta is against Bart Simpson.

Bart Simpson is the primary target of Sideshow Bob’s relentless vendetta. Bob blames Bart for foiling his evil plans and has made numerous attempts to exact revenge on the mischievous boy throughout the show’s long-running history.

Sideshow Bob is a master of deceit.

Sideshow Bob’s intelligence and cunning nature make him an expert manipulator and deceiver. He often employs elaborate schemes and disguises to get his way, making him a worthy adversary for the Simpson family.

Sideshow Bob has a recurring catchphrase.

Whenever Sideshow Bob is foiled or caught in a compromising situation, he often exclaims his trademark catchphrase, “I’ll get you, Bart Simpson!”. This iconic line has become synonymous with his character and is instantly recognizable to fans of the show.

Sideshow Bob has a love for classical music.

Despite his villainous nature, Sideshow Bob has a deep appreciation for classical music. He is frequently seen enjoying music by composers such as Ludwig van Beethoven and Richard Wagner, displaying a more refined side to his personality.

Sideshow Bob has a British accent.

Sideshow Bob’s voice actor, Kelsey Grammer, imbues the character with a distinctive British accent. This choice adds to his sophisticated and cultured persona, making him all the more menacing.

Sideshow Bob has his own family.

While often portrayed as a lone antagonist, Sideshow Bob actually has a family of his own. He has a wife named Francesca and a son named Gino, both of whom share his love for mischief and criminal activities.

Sideshow Bob has a complicated past.

Throughout the series, snippets of Sideshow Bob’s past are revealed, shedding light on his troubled upbringing and his journey to becoming the conniving character we know today. These glimpses into his past add depth and complexity to his persona.

Sideshow Bob has appeared in numerous episodes.

Sideshow Bob has made numerous appearances throughout the history of “The Simpsons”, cementing his status as one of the show’s most beloved and enduring characters. His episodes often revolve around his attempts to outsmart Bart Simpson and seek revenge.

Sideshow Bob is highly educated.

Beneath his villainous exterior, Sideshow Bob is highly educated and possesses a sharp intellect. He is shown to be well-read, often referencing classic literature and displaying a keen understanding of various subjects.

Sideshow Bob has an impressive singing voice.

In addition to his intelligence and sinister nature, Sideshow Bob has a surprisingly beautiful singing voice. He has showcased his vocal talent in several episodes, adding yet another layer to his multifaceted character.

Sideshow Bob has a love for theater.

With his theatrical background, Sideshow Bob has a deep appreciation for the arts, particularly the theater. He often references famous plays and uses his knowledge of the stage to enhance his schemes and plots.

Sideshow Bob is a fan-favorite character.

Sideshow Bob has garnered a dedicated fan following due to his compelling personality, memorable catchphrases, and intriguing storylines. His presence in “The Simpsons” has greatly contributed to the show’s enduring popularity.

Sideshow Bob has his own theme music.

Whenever Sideshow Bob makes an appearance, he is accompanied by his own distinctive theme music, which adds to his sense of menace and sets the tone for his villainous actions.

Sideshow Bob has a passion for crossword puzzles.

A lesser-known fact about Sideshow Bob is his love for crossword puzzles. In some episodes, he is depicted solving complex puzzles with ease, showcasing his sharp mind and attention to detail.

Sideshow Bob has been to prison multiple times.

Due to his numerous criminal activities, Sideshow Bob has spent a significant amount of time behind bars. However, he always finds a way to escape or manipulate his way out, ready to resume his pursuit of vengeance.

Sideshow Bob has a complicated relationship with his brother Cecil Terwilliger.

Sideshow Bob’s relationship with his brother Cecil Terwilliger is often filled with rivalry and animosity. The two have clashed on multiple occasions, showcasing their contrasting personalities and approaches to villainy.

Sideshow Bob’s character is inspired by other iconic villains.

The creators of “The Simpsons” drew inspiration from classic villains, such as Wile E. Coyote from Looney Tunes and Alfred Hitchcock’s psychological thriller characters, to develop the complex and captivating persona of Sideshow Bob.

Sideshow Bob has a fear of rakes.

In one of the show’s most memorable running gags, Sideshow Bob experiences an irrational fear of stepping on rakes. This recurring joke has become a fan favorite and is often humorously depicted throughout the series.

Sideshow Bob has a memorable appearance in the episode “Cape Feare”.

In the iconic episode “Cape Feare”, Sideshow Bob recreates a famous scene from the film “Cape Fear” as he stalks the Simpson family. This episode is widely regarded as one of the best in the series and showcases Sideshow Bob’s relentless pursuit of revenge.

Sideshow Bob is an enduring symbol of villainy in animated television.

With his distinctive persona, memorable catchphrases, and recurring presence in “The Simpsons”, Sideshow Bob has become an enduring symbol of villainy in animated television. His role as Bart Simpson’s arch-nemesis has solidified his place in pop culture history.


From his distinct voice to his devious plans, Sideshow Bob has become one of the most iconic characters in the world of cartoons. With his relentless pursuit of Bart Simpson, he has brought laughter and excitement to fans of The Simpsons for years. Whether you love to hate him or find yourself cheering for his dastardly schemes, Sideshow Bob continues to captivate audiences with his intelligence, wit, and sheer madness.

As one of the longest-running animated shows in history, The Simpsons has given us a plethora of unforgettable characters, and Sideshow Bob definitely stands out among them. With his complex backstory and unforgettable moments, he has become a fan favorite. So, the next time you tune in to The Simpsons, keep an eye out for Sideshow Bob, and remember these 24 fascinating facts about this mischievous character.


1. Who voices Sideshow Bob in The Simpsons?
Kelsey Grammer provides the voice for Sideshow Bob in The Simpsons.

2. What is Sideshow Bob’s real name?
Sideshow Bob’s real name is Robert Terwilliger Jr.

3. Why does Sideshow Bob hate Bart Simpson?
Sideshow Bob hates Bart Simpson because Bart has foiled his plans and sent him to jail multiple times.

4. How long has Sideshow Bob been a character in The Simpsons?
Sideshow Bob has been a recurring character in The Simpsons since the first season in 1990.

5. Has Sideshow Bob ever succeeded in killing Bart?
No, despite numerous attempts, Sideshow Bob has never succeeded in killing Bart Simpson.

6. Does Sideshow Bob have any siblings?
Yes, Sideshow Bob has a brother named Cecil.

7. What is Sideshow Bob’s occupation?
Sideshow Bob is a former sidekick of Krusty the Clown and a former mayor of Springfield.

8. Is Sideshow Bob considered a villain or anti-hero?
Sideshow Bob is generally considered a villain, although he has occasionally shown moments of redemption.

9. What are some of Sideshow Bob’s most memorable episodes?
Some of Sideshow Bob’s most memorable episodes include “Cape Feare,” “Sideshow Bob Roberts,” and “The Italian Bob.”

10. Will Sideshow Bob ever achieve his goal of killing Bart?
Since The Simpsons is an ongoing series, it is uncertain whether Sideshow Bob will ever achieve his goal of killing Bart.