In the colorful world of professional wrestling, unexpected crossovers often create unforgettable moments. One such instance was the appearances of Paul Reubens, famously known as Pee-wee Herman. But how did this childlike character find himself sharing the spotlight with WWE stars? Explore this unlikely crossover and uncover Pee-wee Herman’s hidden influence on many within the wrestling world.
Pee-wee Herman’s WWE moments, from fist-bumping The Rock at WrestleMania XVII to being lifted by Big Show on Raw in 2010, marked an unexpected crossover into professional wrestling. Photo Credit: WWE. Artwork by Pro Wrestling Stories.
From Comedy to Controversy: The Rise of Pee-wee Herman
Pee-wee Herman, created by Paul Reubens, rose to fame with his red bow tie, gray suit, and infectious laugh, becoming a cultural icon before facing controversy in the 1990s. Photo Credit: Everett Collection.
Paul Reubens created the character of Pee-wee Herman, a childlike figure known for his distinctive red bow tie, gray suit, and infectious laugh.
Pee-wee became a cultural phenomenon in the 1980s and 1990s, starring in movies and his own TV show, “Pee-wee’s Playhouse.”
Reubens’ journey to stardom began in the late 1970s when he joined the Los Angeles-based improvisational comedy team The Groundlings. The character quickly gained popularity, leading to a stage show, “The Pee-wee Herman Show,” which ran for five sold-out months.
The success of the stage show caught the attention of Warner Bros., resulting in Pee-wee’s big-screen debut in “Pee-wee’s Big Adventure” released in 1985 and directed by Tim Burton. The film was a critical and commercial success, grossing $40 million and cementing Pee-wee’s place in pop culture.
However, Reubens faced a significant setback in 1991 when he was arrested for indecent exposure in an adult theater. This incident led to the cancellation of “Pee-wee’s Playhouse” and put Reubens’ career on hold for nearly two decades.
A New Stage: Pee-wee Herman’s Surprise WWE Cameo
Pee-wee Herman’s unexpected WWE debut on Monday Night Raw on November 1st, 2010, featured a memorable showdown with The Miz. Photo Credit: WWE.
In 2010, Reubens revived his beloved character, bringing “The Pee-wee Herman Show” back to Broadway. As part of this comeback, Reubens ventured into the world of professional wrestling.
On November 1st, 2010, Pee-wee Herman made his WWE debut on Monday Night Raw. This episode was part of the 2010 Slammy Awards edition, blending the worlds of children’s entertainment and sports entertainment.
The segment began with Pee-wee Herman in the ring, introducing himself as the guest host for the night. He announced that the secret word of the night was “ring,” and whenever someone said it, everyone should scream – a classic callback to his TV show, “Pee-wee’s Playhouse.”
The Miz and Alex Riley then came out to confront Pee-wee, leading to a verbal exchange. The Miz insulted Pee-wee’s outfit and mannerisms, which Pee-wee countered with his classic “I know you are, but what am I?” routine.
The Miz reluctantly participated, much to the audience’s delight.
The interaction then escalated when the 7-foot-tall Big Show (Paul Wight) entered the scene. In a comedic twist, Big Show was dressed similarly to Pee-wee Herman and was introduced as Pee-wee’s cousin, “Big Wee.”
A highlight of this segment came when Big Show effortlessly picked up and cradled Pee-wee, creating a stark visual contrast that drew laughter and cheers from the audience. The segment concluded with The Miz challenging Big Show to a match later that night.
This appearance was well-received and later earned Pee-wee Herman (Paul Reubens) a Slammy Award for “Guest Star Shining Moment of the Year.”
You can watch this memorable segment below:
Behind the Scenes: The Personal Significance of Pee-wee Herman’s WWE Segment for The Miz
Pee-wee Herman’s backstage moment with The Miz during their WWE Raw segment holds personal significance for The Miz, who recalls it as his father’s favorite moment of his WWE career. Photo Credit: WWE.
The segment, particularly the interaction with The Miz, became a memorable moment in The Miz’s career for a very personal reason.
“It’s not main-eventing WrestleMania, it’s not winning the WWE championship—not once, but twice. It’s me getting in the ring and having a verbal argument with Pee-wee Herman.”
Interestingly, the segment almost didn’t happen as planned. The Miz revealed, “Earlier that day, his publicist said that he wouldn’t come out as Pee-wee and that Paul would be himself. I was like, ‘I can’t believe this.’
“So I found him and asked, ‘Can we please do Pee-wee?’ And he said, ‘Of course.’ Then I was all fired up.”
On Instagram, The Miz elaborated on his personal connection to Reubens:
“As a kid I was a huge fan. I saw all the movies, TV shows, I had the Pee Wee Herman PJ onesie that I wore to sleep every night. I became a bigger fan when I met Paul.”
Pee-wee’s WrestleMania Moment Shared with Legends
Pee-wee Herman (Paul Reubens) shares a fist bump with Dwayne “The Rock” backstage at WrestleMania XXVII on April 3, 2011. Photo Credit: WWE.
Following his successful Raw appearance, Pee-wee Herman was invited to attend WrestleMania XXVII on April 3rd, 2011, at the Georgia Dome in Atlanta. This event, often referred to as the “Showcase of the Immortals,” is WWE’s biggest annual spectacle, drawing fans from around the world.
In this appearance, Pee-wee Herman initially admitted to being John Cena’s biggest fan, which was significant given the brewing rivalry between Cena and The Rock at the time.
However, in a comedic turn of events, The Rock managed to sway Pee-wee’s allegiance to become a member of “Team Bring It.”
The segment showcased Pee-wee’s comedic talents as he performed impressions of John Cena and The Rock and mimicked their catchphrases.
This WrestleMania appearance solidified Pee-wee’s place in WWE lore. It showed that his Raw segment wasn’t just a one-off gimmick, but part of a larger integration into the WWE world.
The fact that he was included in a segment with The Rock, one of WWE’s biggest stars, and Mean Gene Okerlund, a beloved figure in wrestling history, highlighted the value WWE placed on Pee-wee’s presence.
This appearance at WrestleMania XXVII came as WWE was setting the stage for the following year’s WrestleMania 28, which would feature a highly anticipated match between The Rock and John Cena. Pee-wee’s comedic switch from Team Cena to Team Bring It added a lighthearted element to this building rivalry.
While Pee-wee’s influence on the eventual outcome of the Rock vs. Cena match remains a playful mystery, his appearance at WrestleMania XXVII stands as a unique moment where the worlds of children’s entertainment and professional wrestling collided on WWE’s grandest stage.
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Pee-wee Herman’s Legacy in WWE
Pee-wee Herman (Paul Reubens) shares a comedic moment with Mark Henry backstage during Monday Night Raw on November 1st, 2010. Photo Credit: WWE.
Paul Reubens’ appearances in WWE, though brief, left a lasting impression. His willingness to fully embrace his Pee-wee persona in a pro wrestling context demonstrated the character’s versatility and Reubens’ commitment to entertainment.
WWE, upon learning of Reubens’ passing in 2023, issued a statement acknowledging his contributions:
“WWE is saddened to learn that Paul Reubens has passed away. Reubens was a beloved entertainer and brought his iconic character Pee-wee Herman to WWE. In that role, he shared the screen with Superstars such as The Rock, The Miz, and Big Show.”
WWE’s official statement further elaborated:
Reubens first appeared in WWE on Monday Night Raw’s November 1, 2010 edition, where he had hilarious interactions with Miz and Big Show.
“His memorable performance earned him a Slammy Award for Guest Star Shining Moment of the Year.
“He was also in attendance as Pee-wee at WrestleMania XXVII, where he appeared in a segment with The Rock and “Mean” Gene Okerlund and admitted to being John Cena’s No. 1 fan.”
How the Wrestling World Reacted to Pee-wee Herman’s Death
Pee-wee Herman’s in-ring moment with Big Show on WWE Raw in 2010. Following Paul Reubens’ passing, WWE stars shared heartfelt tributes. Photo Credit: WWE.
Paul Reubens’ impact on the wrestling community was evident in the reactions from various WWE personalities following his passing.
Corey Graves, WWE commentator, shared on Twitter, “Every year, my friend Paul would bombard me with texts, emails, and occasionally videos wishing me a ‘Happy Birthday.’ His Christmas cards were legendary. I grew up a fan of Pee Wee. I was lucky to become friends with Paul Reubens. May the laughter he gave us all live on forever.”
Adam Copeland, known as Edge in WWE, also expressed his fondness for Reubens, saying, “Every birthday. Every Christmas. Cards. Gifs. Emails. Laughs. Supplied by Paul Reubens. He was a very, very special human being. Who brought untold joy to millions. For decades. Thank you, friend. I’ll miss you.”
The Miz echoed these sentiments, reflecting on Reubens’ kindness and humor. He shared, “Every birthday I would get dozens of funny birthday memes that would make me smile. My birthday is in a couple months and I will truly miss those texts. Thank you for always making me laugh. You will be missed, Paul Reubens. RIP.”
Pee-wee Herman’s Influence on Future WWE Guest Stars
Pee-wee Herman (Paul Reubens) shares a backstage moment with The Miz and The Big Show during his WWE Monday Night Raw appearance on November 1, 2010. Photo Credit: WWE.
Pee-wee’s successful integration into WWE programming paved the way for more diverse guest appearances. It showed that characters from children’s entertainment could effectively engage with the WWE audience, bridging generational gaps.
Following Pee-wee’s appearances, WWE continued to bring in guests from various entertainment backgrounds. This included other comedians, actors, musicians, and even sports figures from outside wrestling. Each of these guests, in their own way, followed the path that Pee-wee helped establish.
It’s interesting to note that Paul Reubens’ influence went beyond his own appearances. Pop artist Poppy, who has made multiple appearances in WWE NXT, mentioned Pee-wee as an inspiration for her work with WWE.
“That was one of my longtime dreams,” she shared. “I wanted to work with WWE and got the idea after I saw Paul Reubens, Pee-Wee Herman, make an appearance on WWE back in the day.”
Reflecting on Paul Reuben’s Impact in Pro Wrestling and Pop Culture
Remembering Pee-wee Herman (Paul Reubens), who embraced the world of sports entertainment with humor and heart. Photo Credit: WWE.
Paul Reubens’ appearances as Pee-wee Herman in WWE may have been brief, but they left a lasting mark on both wrestling and pop culture. His willingness to embrace the wild world of sports entertainment proved that WWE could be a playground for all kinds of characters—no matter how unlikely the crossover.
Pee-wee Herman’s presence in WWE opened the door for future celebrity appearances, showing that with the right mix of humor and heart, even the most unexpected guest could make an impact. Whether it was sharing the ring with The Miz and Big Show or joining “Team Bring It” and fist-bumping The Rock, Pee-wee’s foray into wrestling remains a beloved and unique moment in WWE history.
Reubens’ time in WWE reminds us that wrestling, at its best, is all about bringing people together—no matter where they come from or what stage they’re used to.
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Marc Madison is a long-time contributor for Pro Wrestling Stories as well as editor-in-chief for the website Pro Wrestling Post. He can be reached on Twitter @TheMarcMadison.
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