Top 10 Embarrassing Celebrity Wrestling Moments
Ben Stiller's Figure-Four
10. Battle Dome’s Terry Crews Invades WCW Nitro
In late 2000, the cast of the syndicated show “Battle Dome,” led by Terry Crews aka “T-Money,” crossed into WCW Nitro. The two groups exchanged insults and brawled both in and out of the ring in a storyline that struggled to build interest. Their clumsy brawls and awkward confrontations came off as forced and failed to engage fans. The rivalry eventually saw WCW wrestlers and Battle Dome cast members fighting ringside, but the crossover flopped and is remembered as an uneasy mix of real athletic competition and scripted wrestling drama.
9. Will Sasso’s Sharpshooter Humbling
Comedian and wrestling fan Will Sasso attempted to step into the ring with WWE legend Bret Hart. After antagonizing Hart on television, Sasso accepted a match challenge but was utterly dominated. Hart repeatedly locked him in the Sharpshooter submission hold, forcing Sasso to repeatedly tap out. The segment emphasized Sasso’s lack of wrestling skills and stood out as an awkward celebrity appearance that ended with the comic being embarrassed in the ring.
8. MacGruber’s Explosive Mishap
When the “Saturday Night Live” character MacGruber and his sidekick Vicki St. Elmo guest-hosted Raw, their over-the-top comedic antics seemed more suited to a small studio than a huge arena. The segment concluded with an explosive accident that seemingly “blew up” wrestler R-Truth, leaving only his boots behind. The sketch devolved into an odd, unconvincing storyline involving the Great Khali in a ridiculous costume. The whole cameo confused fans and highlighted the trouble of mixing comedy characters with sports entertainment.
7. Art Donovan’s Confused Commentary
Hall of Fame football player Art Donovan was brought in to add Baltimore charm to the 1994 King of the Ring commentary team. However, his unfamiliarity with wrestling terminology and wrestlers led to constant interruptions with simplistic questions like “Who’s this guy?” and “What’s going on here?” His awkward and baffled commentary amused some but mostly made the broadcast painful to watch, turning a serious event into a confusing spectacle.
6. The Weird WCW Ringside with Chuck Norris and Friends
In January 1999, action stars Chuck Norris and Jean-Claude Van Damme appeared ringside on WCW Nitro alongside NFL star Herschel Walker and NHL legend Brett Hull. Rather than boost the show, their awkward, uncoordinated ringside presence, where Van Damme mimed fighting no one in particular, felt forced and out of place. The celebrities’ lack of real involvement and the unexplainable entrance left fans scratching their heads and added to WCW’s reputation for strange celebrity moments.
5. Macaulay Culkin’s Random Paint Can Assault
Former child star Macaulay Culkin shocked WWE audiences by appearing unannounced during a Raw Falls Count Anywhere match in 2009. In a completely unconnected segment, he hit wrestler Chavo Guerrero over the head with a paint can. The random nature of the attack, with no storyline setup or follow-up explanation, made the cameo feel jarringly out of place—but undeniably memorable for its sheer randomness.
4. Chris Jericho’s Date with “Planet of the Apes”
To promote the 2001 Tim Burton remake of “Planet of the Apes,” WWE’s Chris Jericho set up Stephanie McMahon on a comical date with two actors in ape costumes. Though meant to be humorous marketing, the odd scene bordered on bizarre and left many wrestling fans puzzled. It was an awkward mix of movie promotion and wrestling storyline that didn’t land as intended, contributing to Jericho’s controversial and often irreverent wrestling persona.
3. Ben Stiller’s Painfully Awkward Figure-Four
Ben Stiller’s 1999 WWE Raw cameo quickly turned into one of the most uncomfortable celebrity moments in wrestling history. Invited to the ring by Jeff Jarrett for a promo plug of Stiller’s movie “Mystery Men,” the actor was distracted and clearly out of his element. After an awkward interview, Stiller was blindsided and trapped in the punishing Figure-Four Leglock, highlighting his wrestling inexperience and the segment’s overall cringeworthy tone.
2. Kurt Russell & Courtney Cox Mock David Arquette
At the height of David Arquette’s controversial WCW World Championship reign, his then-wife Courtney Cox and movie co-star Kurt Russell appeared on Nitro to mock his title run. The out-of-place Hollywood walk-on poked fun at Arquette, exacerbating fans’ disbelief over his holding the belt. The segment embodied the absurdity of that era in WCW, turning what could have been a celebrity endorsement into an embarrassing public roast.
1. Elvira’s Cringe Commentary at WrestleMania 2
At WrestleMania 2 in 1986, cult horror icon Elvira joined the commentary team alongside beloved announcers Jesse Ventura and Lord Alfred Hayes. Unfortunately, her quirky “Mistress of the Dark” persona clashed with the smooth delivery of seasoned commentators. Her awkward, stilted attempts at commentary were met with silence and confusion, making her the subject of one of wrestling’s most cringe-worthy celebrity moments on its grandest stage.
