One of the fun aspects of the professional wrestling business is when celebrities get involved. When someone like Lawrence Taylor put the work into their appearance, fans get a memorable experience for all the right reasons. Even if he or she wasn’t necessarily a fan – if they put the work into their appearance, it shows.

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It shows even more when they don’t put the work in at all. While not every appearance can be great, if WWE fans aren’t enamored with you, one of two things might have happened. One, sadly, whatever your schtick was, it just didn’t connect with the fans. But even worse, downright egregious, is that you showed up woefully underprepared.
10
The Cast Of Hot Tub Time Machine
An Excuse For Divas Gone Wild
- The cult comedy was released in 2010.
- The Divas title debuted in 2008 and lasted until 2016.
- The cast joined the March 29, 2010, edition of Raw.
Recent years have proved wrestling fans want to see female wrestlers working serious matches inside the squared circle, regardless of how pretty they are.
Which is why silly marketing stunts like the ladies hanging out in the Hot Tub Time Machine to promote the eponymous movie with that cast haven’t aged well.
9
Dennis Miller’s Comedy Didn’t Connect With WWE Fans
It’s A Taste The WWE Fans Didn’t Acquire
- Miller became famous as the host of Weekend Update on SNL.
- The acerbic comedian was Guest Host on the December 14, 2009 Slammy Awards edition of Raw.
- Miller grew up in the land of Bruno Sammartino, Pittsburgh, Pennsylvania.
For fans of Dennis Miller, he is one of the funniest men alive. If you’re not a fan, he seems like a guy who is too smart for his own good. That kind of bravado would generally fit right in with wrestling (see Andy Kaufman, for example).

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When Miller came to Raw for the 2009 Slammy Awards, none of his jokes hit at all – even for his own fanbase. Just like on Monday Night Football, the acerbic comic seemed out of place on Monday Night Raw.
8
Jewel & Ty Murray Bring Bull Riding To Raw
Dreams Thankfully Didn’t Last Long For The Country Couple
- Jewel became a household name with her 1995 album, Pieces Of You.
- Murray was part of the 2009 season of Dancing With The Stars.
- The couple hosted the February 22, 2010, edition of Raw.
While Raw is always a good place for promoting your projects, sometimes creating a brand synergy is a true chore. A chore that is evident watching the show. Bull rider Ty Murray and then-wife, singer Jewel, arrived on Monday Night for what else – a Diva Mechanical Bull Riding Contest!
During this era, anytime a singer came to Raw, they had to endure a few quick bars from Jillian Hall, which meant a soul-shrieking rendition of “You Were Meant For Me.”
Gorilla Monsoon & Randy Savage Were Audibly Annoyed
- Donovan guest-commentated on the 1994 King Of The Ring.
- First ever Colt to enter the Pro Football Hall Of Fame in 1968.
- The main event is the much-maligned Lawler Vs. Piper dream match.
In the old days, one way to try and drum up ticket sales when WWE, or any other territory, came to town would be to feature a local star. For the 1994 King Of The Ring, the WWE came to Baltimore and enlisted the help of local sports legend, Art Donovan.
But while Art knew a heluvalot about his chosen sport, he didn’t know anything about WWE. Thus, the third man in the booth sounded less than stellar and not even ‘Macho Man’ Randy Savage and Gorilla Monsoon could pull him through.
6
Maria Menounos
She Just Failed To Bring It At WrestleMania 28
- Maria and her husband, Keven Undergaro, produced X-Pac’s podcast.
- She co-hosted Raw in 2009.
- Menounos inducted her friend, Bob Backlund, into the 2013 WWE Hall Of Fame.
Plenty of celebrities have worked major matches at WrestleMania. You can add Maria Menounos to that list as well. The unabashed Superfan came to the 28th Showcase Of The Immortals ready to throw down, alongside Kelly Kelly against Beth Phoenix and Eve Torres.

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The babyfaces were outgunned before the bell even rang. The match was practically the squash that it sounded like on paper. But give the reporter credit, as she muscled through with several broken ribs.
5
Lavar Ball & Sons Could Only Toss Slip-Ups
Even The Miz Couldn’t Corral Him In
- Lavar is a former football player and all of his sons played in the NBA.
- LaVar Ball was totally unscripted and unprofessional.
- The Balls were on the June 26, 2017 edition of Raw.
When your entire business is built upon blurring the lines between work and shoot, you’re occasionally bound to get folks on your TV that legitimately think all of wrestling is a shoot. There’s not much else of an explanation as to why LaVar Ball and his sons came to Raw without a clue as to what to say or do.
Ball swore up a storm and ripped his shirt off, wanting to do battle with The Miz. The A-Lister, who is usually over-prepared for celebrity moments, was almost as in much shock as the fans watching the debacle.
4
Reverend Al Sharpton Was Woefully Out Of Place
Part Of The Bottom Of The Guest Host Era
- Al Sharpton came to prominence as a Civil Rights activist in New York.
- Sharpton was once Funk Legend James Brown’s manager.
- Rev. Sharpton guest hosted Raw in September 2009.
There perhaps couldn’t have been a more mismatched pairing than Civil Rights Activists Reverend Al Sharpton and Monday Night Raw. He came to Raw to help promote his Education Reform Tour, a noble reason.
But for whatever reason, the WWE fans booed Reverend Al out of the building and not even the combined efforts of Chris Jericho and MVP dueling on the mic could get Al over.
3
Mr. T Really Loves His Mother
The 80’s Icon Got A Hall Of Fame Cutoff
- Mr. T was an integral part of the early days of the Rock N’ Wrestling Connection.
- He was one of the few celebrities to wrestle on both WrestleMania and Starrcade.
- Mr. T made amends with Roddy Piper at WrestleMania 30.
Mr. T wasn’t just a major part of the Rock ‘n’ Wrestling Connection, he was a huge part of Eighties Pop Culture in general. He was so popular that he once wrote a song espousing the love he had for his mother and how all good children should respect their mothers.
It’s an odd but fun song when you pair it with Mr. T’s unending Hall Of Fame speech where he did the same thing. He’d probably still be going today if Kane didn’t arrive to give him the hook.
2
Bob Uecker Meant To Embarrass Himself
The Beloved Baseball Zero Got Choked Out
- Mr. Baseball is one of the longest-running MLB broadcasters in history.
- Bob Uecker was part of WrestleManias 3 and 4.
- Eucker was inducted into the 2010 WWE Hall Of Fame.
Bob Uecker is one of the most beloved sports broadcasters and occasional comedic actors on the planet. His entire schtick was built upon being the butt of a joke. Which puts his appearances at both WrestleManias 3 and 4 in some of the most memorable in WWE history.

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He spent most of WrestleMania 4 searching for Vanna White and getting choked out by Andre The Giant. One year earlier, he was getting ribbed incessantly by Jesse Ventura.
1
Jeremy Piven Couldn’t Get A Clue
He Thought WWE’s SummerSlam Was Called “Summerfest”
- Piven had a career resurgence playing Ari Gold on HBO’s Entourage.
- Ken Jeung showed up on the same episode and got beat up by John Cena.
- Piven hosted the August 4, 2009, edition of Raw.
In the most under prepared moment in celebrity promotion history, Jeremy Piven showed up on Raw to promote his then-upcoming movie, The Goods, but to also promote that year’s SummerSlam. Certainly someone in WWE told him the name of the show before he got to the ring, but he still called it “Summerfest.”
Instantly un-endearing himself to the WWE fanbase, but over the years T-Shirts celebrating the major gaff have popped up for fans to wear ironically.
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