Mixing celebrities and sports-entertainment is nothing new. Long before Cyndi Lauper accompanied Wendi Richter to the ring for a match on MTV, before Drew Carey got inducted into the WWE Hall of Fame, even before Robocop saved Sting from The Four Horsemen, pop culture stars like 1930's world champion boxer Primo Carnera were climbing into the squared circle.

The relationship between sports and entertainment and sports-entertainment is a natural one, but that doesn’t mean things always go smoothly. For every Bob Barker, there have been countless celebrities who have adapted to the ring with the ease of Mike Adamle forming a coherent sentence. And while no wrestling fan can forget the embarrassing turns of stars like Jay Leno and David Arquette, few remembers Ben Stiller’s run-in with Jeff Jarrett, Kurt Russell’s Nitro walk-on and 11 other uncomfortable celebrity cameos that WWEClassics.com is more than happy to bring to your attention.

Ben Stiller

Ben Stiller gets put in the dangerous Figure-Four Leglock by Jeff Jarrett.

If you wanted awkward, you certainly got it during Ben Stiller’s surprise appearance on a July 1999 episode of Raw. Stiller was in town to promote his movie, “Mystery Men,” when Intercontinental Champion Jeff Jarrett invited him into the ring. What happened next was, quite possibly, the most awkward interview in wrestling history.

Stiller was unable to keep his eyes off Jarrett’s manager — the stunning Debra — as he snuck in an extended plug for his new superhero flick. But when the actor went too far with his flattery for the blonde, Double J blindsided Stiller and twisted the tiny comic’s stems with the Figure-Four Leglock. Before he could snap Stiller and save the world from more “Meet the Parents” sequels, Jarrett was interrupted by D’Lo Brown, who nailed the Tennessean with a ring-rocking Sky High. — BOBBY MELOK

Kurt Russell & Courtney Cox

Courtney Cox & Kurt Russell give their thoughts on new WCW Champion David Arquette.

On May 1, 2000, David Arquette was in the midst of his baffling reign as WCW Champion. At the time, it seemed as though the only people who believed in him were his friends Diamond Dallas Page and Chris Kanyon. That was made especially clear when WCW cameras caught Arquette on the set of the movie “3000 Miles to Graceland,” where his then-wife, Courtney Cox, was pleading with him not to compete. During their spat, the film’s star, Kurt Russell, complete with Elvis sideburns, told Courtney to report to the set to film a “nude love scene,” before laughing at the fact that Arquette was WCW Champion.

The appearance on Nitro by the Hollywood mega-stars was pretty neat, but it was also a bit bizarre — kind of like the entire WCW Title reign of David Arquette. — KEVIN POWERS

Andy Warhol

At the height of the Rock ‘n’ Wrestling Connection’s mainstream appeal in the mid-80s, WWE and its monthly shows at Madison Square Garden had become such an integral part of the New York City scene that art world icon Andy Warhol considered himself a bona fide Hulkamaniac.

For archival proof, check out this stilted conversation between “Mean” Gene Okerlund and the man who turned Campbell soup cans into modern art. Comingling in Hulk Hogan’s locker room moments after The Hulkster dispatched “Rowdy” Roddy Piper at MTV’s landmark “The War to Settle the Score,” Warhol — looking like he was just stirred from a winter’s sleep — called WWE “the most exciting thing” he’d seen in his whole life. Had Warhol not passed away soon after, there’s a chance The Immortal One could’ve become his next great muse. — RYAN MURPHY

Macaulay Culkin

Macaulay Culkin helps out Hornswoggle with one of his classic pranks on Chavo Guerrero.

Twenty years removed from his hilarious turn as Kevin McAllister in the first two “Home Alone” flicks, former child star Macaulay Culkin proved he hadn’t lost any of his adolescent charm when he smashed Chavo Guerrero in the head with a paint can on Raw. Confused? Allow us to explain.

At the time, Chavito was on the losing end of an endless rivalry with Hornswoggle. On Aug. 17, 2009, the former Cruiserweight Champions were tangling in a Falls Count Anywhere Match that led Guerrero into the bowels of the arena. When Guerrero opened the wrong door, Culkin just so happened to blast his forehead with a can of Sherwin Williams that left a bruise that was uglier than Buzz’s girlfriend. At a time when Raw was regularly besieged by celebrity guest hosts, Mac’s cameo was completely random, completely unexplained and, yeah, we’ll admit it, completely awesome. — R.M.

The cast of "Planet of the Apes"

Chris Jericho monkeys around with creatures from "The Planet of the Apes."

Before the 2001 Mark Wahlberg-led remake “Planet of the Apes” won the Oscar for “best movie ever made,” the flick needed a little promotion. That’s why two of the simians from the Tim Burton movie were shoehorned into an August 2001 episode of Raw.

At the time, Chris Jericho and Stephanie McMahon were embroiled in a rivalry that mostly consisted of Y2J saying really offensive things to Mr. McMahon’s daughter in front of millions of people. That night, WWE’s first-ever Undisputed Champion pushed the boundaries of good taste by setting Stephanie up on a date with two of the monkeys from the action movie. If you’ve read Jericho’s second book, “Undisputed,” you’ll know that this segment was a brilliant bit of marketing on the Fozzy frontman’s part. If not, you’ll just be really confused. — R.M

Chuck Norris, Jean Claude Van Damme, Brett Hull & Herschel Walker

After a big win for Goldberg, Chuck Norris, Jean Claude Van Damme, Brett Hull & Herschel Walker share the moment of victory.

On Jan. 15, 1999, WCW Nitro cameras captured the once-in-a-lifetime meeting of action stars Chuck Norris and Jean-Claude Van Damme, NFL great Herschel Walker and NHL Hall of Famer Brett Hull as the foursome sat ringside, enjoying the evening with their families. It seemed like an especially cool sighting at first, but this was WCW, so things immediately got awkward.

After Goldberg defeated Scott Norton and then dismantled the lamer member of The New World Order, he celebrated his victory when the celebrity group entered the ring for no apparent reason. While Hull struggled to get through the ropes, Van Damme entered with fists raised — at no one. The four stars congratulated Goldberg and then left the ring with him. Nothing was promoted, Chuck Norris’ beard delivered not one roundhouse kick and, more than 10 years later, we still can’t make sense of it. — K.P.

Art Donovan

Art Donovan calls the action during the Razor Ramon vs. Bam Bam Bigelow match.

For the most part, pro football and WWE have had a great relationship. Whether it’s legends like Ernie Ladd and Wahoo McDaniel battling in the ring during the offseason, or current sensations like Clay Matthews guesting on Raw, most gridiron stars make an easy transition to the squared circle.

Except for Art Donovan. The Pro Football Hall of Famer joined Gorilla Monsoon and “Macho Man” Randy Savage to call the 1994 King of the Ring pay-per-view, but Donovan’s unfamiliarity with WWE led to commentary that was entertaining for all the wrong reasons. Watching the Superstars in awe, he constantly pestered his colleagues with questions like, “Who’s this?,” “Who are we talking about?” and, most famously, “How much does this guy weigh?” Donovan was meant to bring a little Baltimore charm to the broadcast. Instead, it was like watching sports-entertainment with your grandpa. — B.M.

MacGruber & Vicki St. Elmo

R-Truth makes an explosive exit thanks to Kristen Wiig & Macgruber.

The Meadowlands was temporarily transformed into Rockefeller Center when the cast of the “Saturday Night Live” sketch “MacGruber” guest hosted Raw. A movie based on the “MacGyver” parody was on its way, but it wasn’t fan favorite Will Forte or “Bridesmaids” star Kristen Wiig who performed hosting duties. Instead, they entered the arena in character as goofy government agent MacGruber and his plucky sidekick Vicki St. Elmo to confront the disgruntled Vladimir Kozlov.

The two comedians seemed out of place playing to the Izod Center crowd — a much larger venue than Studio 8H. After the bumbling MacGruber’s explosives accidentally detonated on an unsuspecting R-Truth, only a pair of Truth’s boots remained smoking on the entrance stage. The awkward gag resulted in a bout pitting Kozlov against MacGruber and “Khaluber” — The Great Khali in a ridiculous getup and mullet wig. Even the film’s co-star Ryan Phillippe made a last-minute appearance, leaving the audience wondering if they were a victim of cruel jokes or cruel intentions. — ZACH LINDER

Will Sasso

Will Sasso tries his luck against the legendary Bret Hart.

Comedian Will Sasso is a huge fan of sports-entertainment. His impressions of the squared circle’s biggest Superstars are impeccable. However, the funnyman’s antics tend to earn him a beating when he takes it too far.

Sasso angered Bret Hart during the “Hit Man’s” guest spot on "Mad TV" and ended up in The Sharpshooter. Looking for retribution, the comic showed up on Nitro and cost Hart the United States Title. So, the WWE Hall of Famer challenged Sasso to a match. Surprisingly, the rotund funnyman accepted and took a vicious beating in a one-sided affair that ended with Sasso once again tapping out to The Sharpshooter. — K.P.

Mary Tyler Moore

Mary Tyler Moore gives her thoughts on Rhythm & Blues.

One of the most iconic personalities in television history had her WWE moment in 1990 at WrestleMania VI in Toronto. Sitting at ringside, Mary Tyler Moore was “rewarded” for her support of Jake Roberts. After “The Snake” hit The Million Dollar Man with his patented DDT, he handed out the wealthy Superstar’s Ben Franklins to the folks in the front row — including Ms. Moore.

Additionally, Sean Mooney was able to garner an interview with MTM, who extolled the virtues of HTM, aka the Honky Tonk Man. We’re pretty sure Mary wasn’t familiar with the Elvis impersonator’s career, but she applauded the song the rockabilly singer debuted that night, “Hunka, Hunka, Hunka Honky Love.” — HOWARD FINKEL

Arli$$

HBO star Arli$$ sits in on commentary for Nitro.

If you were expecting Robert Wuhl — the actor who appeared in "Batman," "Bull Durham" and "Good Morning, Vietnam” — you might want to look elsewhere. On July 19, 1999, Wuhl appeared on Nitro in character as Arliss Michaels, the sports agent from the HBO series of the same name.

WCW stars appeared on the sitcom and now Arliss was coming to Nitro to “scout talent.” He joined Bobby Heenan and Scott Hudson — both refusing to acknowledge the goof — at the announce desk as Randy Savage took on Kidman. When Dennis Rodman attacked Savage, Arliss jumped into the middle of the fracas and tried to sign Rodman to his agency. Hilarity ensued. — K.P.

Elvira

Elvira joins the commentary team for WrestleMania 2 in Los Angeles.

Want to see something really scary? Check out quirky scream queen Elvira at WrestleMania 2 in 1986, where she joined Jesse “The Body” Ventura and Lord Alfred Hayes in the announce position for commentary so stilted you might think the “Mistress of the Dark” was quoting an Ed Wood flick.

A uniquely 1980s celebrity, Elvira had evolved from a Los Angeles TV horror host to cult celebrity with her unique blending of vampire chic and California Valley girl ditz. Her gift was her gab — not to mention her traffic stopping figure — but on The Grandest Stage of Them All, she struggled to get a word in edgewise alongside the loquacious “Body.” Apparently, it’s a lot easier for your star to shine when your cohosts are corpses. — H.F.

Terry Crews

The competitors of "Battle Dome" pick a fight with the stars of WCW.

In late 1999, “Battle Dome” debuted in syndication as an edgier version of “American Gladiators” for the new millennium. The competitive show featured a number of colorful personalities battling each other as well as regular Joe contestants in high concept challenges for championships and cash prizes.

On the Nov. 6, 2000, Nitro, “Battle Dome” stars like Michael O'Dell and Bubba King had front row seats for the broadcast where they got into a confrontation with WCW stars like Rick Steiner and Diamond Dallas Page. “Battle Dome” was actually pretty awesome, but there was little interest in a rivalry between the two waning organizations. By the time Steiner showed up on the “Battle Dome” show to battle T-Money — better known as actor Terry Crews — the two groups were well on their way to entertainment obscurity. — K.P.