The Hilarious Evolution of Paul Reubens: Unveiling His Top 10 Funniest Cameo Roles

The comedic world suffered a great loss with the passing of Paul Reubens at the age of 70. Remembering his incredible talent, let's take a look back at some of his most hilarious comedic cameos. While he is best known for his iconic character, Pee-Wee Herman, Reubens brought his one-of-a-kind sensibility to every project fortunate enough to have him. Apart from his own notable works like Pee-Wee's Big Adventure and Pee-Wee's Playhouse, Reubens also made memorable appearances in various films and sitcoms. Whether it was a brief role in a film or a single episode appearance on a sitcom, Reubens had a knack for stealing the show and leaving a lasting impression. His exceptional talent was always evident, as he left an indelible mark wherever he went. Here, we celebrate Paul Reubens' ten most comedic and unforgettable cameo performances.

10 Penguin's Father in Batman Returns

In 1992, Reubens reunited with his Pee-Wee's Big Adventure director, Tim Burton, for a brief appearance in Batman Returns. Portraying the wealthy father of the monstrous Penguin, Reubens effectively conveys a darkly humorous critique of the ultra-wealthy, without uttering a single line. Through his performance, the audience is truly convinced that his character is so snobbishly superior that he would abandon his own son to live amongst circus penguins. This portrayal successfully establishes the movie's peculiar, gothic atmosphere, which pervades throughout.

9 Prof. Parenthesis in Phineas and Ferb

In the latter part of his career, Reubens showcased his vocal prowess in numerous animated projects, notably as Jokey Smurf in the live-action Smurf movies. However, it was his unforgettable guest appearance on Phineas and Ferb as the diabolical flea scientist, Prof. Parenthesis, that truly stands out. Parenthesis, with his adorable charm characteristic of Phineas and Ferb characters, reaches new heights thanks to Reubens' exceptional performance. Throughout the episode, one recurring gag revolves around Parenthesis' mispronunciation of words, and Reubens masterfully delivers these lines, skillfully emphasizing the most peculiar syllables.

8 Pee-Wee Herman in Comedy Bang! Bang!

7 Sir Terrence Bernadino in Reno 911!: Miami

In 2013, Reubens brought back the beloved character Pee-Wee Herman for a Halloween episode of the talk show parody Comedy Bang! Bang!. Pee-Wee arrived dressed as a cowboy and even brought his delicious homemade ranch double-baked potatoes for the host, Scott Aukerman. It was a delight to witness Reubens embody the Pee-Wee character once again after all these years. Although Pee-Wee would later make a triumphant return to the big screen in Pee-Wee's Big Holiday, it was heartwarming to see the character make smaller appearances on shows like Comedy Bang! Bang! before that.

In both the Reno 911: Miami movie and its preceding series, Terry, portrayed by Nick Swardson, consistently makes outlandish claims about his life, particularly his affluent father, Sir Terrence Bernadino. The rest of the Reno 911 gang understandably doubts Terry's assertions. However, towards the end of the film, a surprising twist reveals that Terry had been telling the truth all along and that his father is played by the talented Paul Reubens. This revelation serves as a satisfying punchline to a long-running joke, with Reubens delivering a standout performance that ties together all of Terry's seemingly unbelievable tales and legitimizes them.

6 Lawyer in Portlandia

When Fred Armisen and Carrie Brownstien's "eccentric individuals" find themselves apprehended and facing trial, they are fittingly assigned an unconventional attorney, portrayed by Reubens, to represent them. The comical sketches featured in Portlandia possess an absurd and zany quality that aligns perfectly with Reubens' talents, making him an ideal fit for any type of character within this realm. His defense speech for these offbeat characters is not only uproarious but also serves as a brilliant embodiment of Paul Reubens' core values. Throughout his career, he consistently championed the cause of those on the fringes and embraced the spirit of whimsical misfit characters. Through this particular speech, he effectively expresses this sentiment in an exaggerated, comedic manner.

5 FBI Agent in Matilda

Reubens's appearance in Danny DeVito's Matilda is brief, but his impact is immense. Departing from his usual comical persona, Reubens mesmerizes as a rigid FBI agent who lacks a sense of humor. However, he is no match for the brilliant young Matilda, who manages to outsmart him effortlessly. This performance showcases Reubens's remarkable versatility, as his character is a complete departure from the beloved Pee-Wee Herman. Despite not altering his physical appearance, Reubens completely immerses himself in the role, convincingly portraying the serious and unwittingly laughable character.

4 Lock in The Nightmare Before Christmas

The Nightmare Before Christmas has the unique distinction of becoming a timeless classic for not one, but two highly celebrated holidays. What sets this stop-motion masterpiece directed by Henry Selick apart is its ability to captivate audiences during both Halloween and Christmas seasons. Notably, Reubens ingrains his indelible mark as the voice behind the mischievous Lock, one of the children entrusted with the task of kidnapping Santa Claus. Displaying his youthful exuberance, Reubens breathes life into the character and even lends his vocals to the iconic song, "Kidnap the Sandy Claws." This song stands as a pinnacle moment within the film, and in true testament to its enduring popularity, Reubens often graced the stage alongside Danny Elfman to perform it live, once the film had secured its status as a beloved classic.

3 Pee-Wee/Desk Clerk in Cheech and Chong's Next Movie

Prior to his iconic film, Pee-Wee's Big Adventure, Reubens showcased his Pee-Wee character in his stand-up and sketch comedy performances. This caught the attention of numerous influential comedians at the time, including the famous stoner duo Cheech and Chong, who eagerly incorporated Reubens and his character into their own movie, Cheech and Chong's Next Movie. Remarkably, Pee-Wee stood out amidst the absurdity of this comedy, demonstrating his universal appeal. This film appearance served as a stepping stone for Pee-Wee, leading to his own successful film series, a Broadway show, and a television program. What sets Pee-Wee apart is his ability to captivate audiences, whether it be in a risqué Cheech and Chong production or in a wholesome, family-friendly adventure.

2 Paul in What We Do in the Shadows

In the episode titled "The Trial" of the vampire reunion series "What We Do in the Shadows," a number of renowned actors, who previously portrayed iconic vampires, make cameo appearances as jury members for the main characters. In this uproarious sitcom, Reubens delivers a standout performance, essentially reprising his role from the television show Buffy the Vampire Slayer. He fully commits to the role, demonstrating his unwavering dedication even in the most absurd of characters. What initially could have been a mere nostalgic reference transforms into a side-splitting joke, thanks to the collective effort and impeccable comedic timing of the entire cast, with Reubens particularly shining.

1 Gerhardt Hapsburg in 30 Rock

Reubens’ appearance in season one of 30 Rock is a standout moment in both the show and his career. Playing the role of Gerhardt Messerschmit Rammstein Von Hap, a spoiled brat and prince of Austria, Reubens showcases his exceptional talent for character work and physical comedy. His comedic chemistry with Jane Krakowski's character, Jenna Maroney, is undeniable, and despite only appearing in one episode, Gerhardt has become a fan favorite. This particular episode is where 30 Rock truly hits its comedic stride, demonstrating the impact that Paul Reubens' talent can make.