As a lifelong fan of WWE, I have always been surprised by the lack of respect that the general public has for professional wrestling as a unique form of entertainment. If you need evidence of how entertaining this product can be, just look at the litany of cultural icons who have requested to make guest appearances. Grammy winning artists, box office superstars, and even some influential politicians have all stepped foot within the WWE's squared circle. While most celebrities say they enjoyed their experiences with the WWE, there are a handful that haven't. As such, this list will name 8 celebs who enjoyed their guest appearances in WWE, and 7 who might have not.
There doesn't seem to be any pattern for determining which celebs will enjoy their time in the ring, but you do get a sense that the ones who watched wrestling as kids/continue watching in adulthood were more accepting of the quirks of the wrestling industry. Some of the entries on this list were one-off performances, while other celebs have chosen to make their time with WWE significantly longer. If you can think of any memorable celebrity appearances which did not make our list, feel free to mention them in the comments.
15 Loved - Stephen Amell
With most celebrity appearances on WWE, one of the biggest issues that producers have to contend with is that the celebs are incapable of doing a lot of the athletic maneuvers that WWE superstars usually perform. This was not the case with Stephen Amell, as the Arrow star was clearly as athletic (if not more athletic) than his wrestling counterparts. Amell famously had an intense training regiment for his role as Oliver Queen, and this helped him to quickly acclimate to the squared circle. Not only was Amell well suited to professional wrestling, he also enjoyed his time with WWE. Amell watched wrestling as a child, and he admitted that he used to imagine himself as World Champion. Being able to perform with adept performers like Cody Rhodes (Stardust) and Neville certainly didn't hurt his experience either.
14 Regret - Floyd Mayweather
Boxing purists were up in arms in 2017 over the media circus surrounding the Conor McGregor-Floyd Mayweather super fight. The fight was certainly a spectacle, but some commentators speculated that this match would be more hype than substance, as the MMA fighter was clearly going to be overmatched by the undefeated Mayweather. This wasn't the first time that "Money" Mayweather was involved in this kind of spectacle, however, in WrestleMania XXIV, Mayweather signed on to be in a highly publicized match with "the World's Largest Athlete," the Big Show. Everyone expected Mayweather to win this scripted match, just like they expected him to win his legitimate contest against McGregor. People close to Mayweather have worried that these circus-like arrangements could somehow tarnish the legacy of Floyd the boxer.
13 Loved - Kevin Hart
If you need any evidence of Kevin Hart's love for the WWE, look no further than the various tribute videos that Hart has done for former wrestlers. In the Hall of Fame tribute videos for both Sting and Goldberg, Hart was prominently featured describing how these wrestlers changed his formative years growing up. Given how big a fan of WWE he is, it must have been pretty great for him to be featured as the guest star on Monday Night Raw. Even better than that, Hart has starred in two separate movies alongside Dwayne "The Rock" Johnson. Johnson, of course, got his start in WWE, so these two have more than their flourishing acting careers in common.
12 Regret - Chad Ochocinco
Even growing up, I never understood the hype surrounding Chad Johnson (Johnson officially changed his last name to Ochocinco). He was an extremely talented receiver, who had a penchant for flashy displays on the field, but didn't we already have that in the NFL with Terrell Owens? Ochocinco always seemed like he was desperate for attention, and one of his attempts to garnish some media highlights included a foray into the WWE. While this may have been fun for the Bengals wideout, his obsession with the media began to have a negative impact on his playing ability. The ultimate result of this was his utter failure to make an impact as a member of the New England Patriots (who were boasting perhaps the greatest quarterback of all time), and his ultimate dismissal from the league.
11 Loved - Jon Stewart
Just because his storyline drew the ire of many hardcore WWE fans, doesn't mean that Jon Stewart didn't enjoy his foray into the world of professional wrestling. At the recent Summerslam pay-per-view, John Cena was set to challenge Seth Rollins for the WWE Championship. This match was especially momentous because if Cena won, it would have been 16th World Championship, tying him with Ric Flair for the most all time. In such a big moment, WWE allowed Stewart to assist Seth Rollins (a man he had been feuding with for the past year) in defeating John Cena. The next week, Stewart explained that he helped Rollins because he did not want Cena to tie Ric Flair's record. This did not sit well with many WWE fans, but for a lifelong fan like Stewart, it was certainly a once in a lifetime moment.
10 Regret - Donald Trump
When I was thinking of celebrities who might regret making a WWE appearance, our next entry is one that easily jumped off the page. When Donald Trump signed on to be a significant part of the leadup to WrestleMania 23, I doubt he knew that in less than a decade he would become the 45th President of the United States. For someone who has had to combat rumors of his fitness for office, I doubt that videos of him tackling Vince McMahon helped his case very much. Trump and the McMahons have been friends for a number of years, and the two companies heavily collaborated on some of the early WrestleMania events (some were even held at Trump properties in New Jersey). After a tumultuous first year as President, Trump can use all the good PR he can get, and this doesn't include him mixing it up with WWE's finest in the Hall of Fame's celebrity wing.
9 Loved - Seth Green
A huge caveat of being a guest star for WWE, is that you don't know what kind of storyline or superstars they are going to pair you with when you make your appearance. You could say that veteran actor Seth Green hit the jackpot with his appearance, as he got to team with two surefire WWE Hall of Famers. Green not only got to appear with both John Cena and Triple H, he actually competed in a match alongside the two wrestling behemoths. Green has admitted to being a huge WWE fan in the past, so he probably would have been happy no matter who he was paired with. But starring alongside two of WWE's biggest stars had to have been icing on the cake for him.
8 Regret - Wiz Khalifa
Our next WWE appearance that a celebrity regrets is one that I was actually there for live. When Wiz agreed to perform at Monday Night Raw in his hometown of Pittsburgh, Pennsylvania, i imagine that he was expecting a pretty friendly audience. Instead, he was met with a chorus of boos, and an audience that was (at best) apathetic to his performance. Many WWE fans are inherently hostile to these guest appearances, and having to sit through 10 minutes of a non-wrestling entertainment didn't sit well with many of the Pittsburgh fans. Therefore, though he did enjoy a few funny segments with WWE (like the one featured above), I'm willing to guess that Wiz won't be looking to perform on Raw again anytime in the near future. The WWE crowd has become too fickle for these rushed celebrity appearances to work like they once did.
7 Loved - Shaquille O'Neal
An easy way to tell if a celebrity guest star actually enjoyed their time in WWE is if they schedule to make a subsequent appearance. Given the fact that NBA legend Shaquille O'Neal was in talks to compete in an actually match against the Big Show, I'd say the Shaqtus enjoyed his WrestleMania moment. At WrestleMania 32, Shaq was a surprise entrant in the Andre the Giant Memorial Battle Royal. Though he didn't win, Shaq did eliminate the Big Show, potentially setting up a match with the friendly giant at a subsequent PPV. Scheduling conflicts have kept this match from happening, but don't be surprised if we see these two giants go at it again in the near future. The Big Diesel's larger than life personality seems perfectly tailored for a WWE ring.
6 Regret - Mike Tyson
I debated on which side of this article to list Mike Tyson (of if I should list him at all), because Tyson's feelings about his WWE experience seem to change more often than the weather. As one of the greatest boxers of all time, and the "baddest man on the planet", Tyson was a huge get for the WWE in the '90s. Tyson perfectly fit with the Attitude Era, and his segments with Stone Cold Steve Austin and D-Generation X were pure magic. With that being said, Tyson has made some disparaging comments about his time with WWE. According to Tyson, several WWE superstars were rude to him backstage, and were jealous of the opportunities and TV time that he was getting. I have some doubts about the truthfulness of this, just for the simple fact that these Superstars would have had to be crazy to be rude to a guy like Tyson.
5 Loved - Ben Roethlisberger
I think that the majority of WWE fans would support me when I say that the majority of WWE celebrity appearances are pretty lame. They often seem rushed, and they rarely advance the storyline of the actual WWE superstars. One exception to this, and perhaps my favorite WWE celebrity appearance, was when Ben Roethlisberger and his offensive line appeared on Monday Night Raw in Pittsburgh. Roethlisberger has won two Super Bowls as the quarterback of the Steelers, so he's quite the fan favorite in Pittsburgh. Therefore, it was great for both Ben and the Pittsburgh fans when WWE scheduled him, and his beefy offensive line, to take down the Big Show. Roethlisberger clearly enjoyed the segment, and has been featured in the WWE crowd almost every time that they come to Pittsburgh.
4 Regret - David Hasselhoff
As fun as WWE appearances are for some celebrities, there are others who think that it is beneath them to spend time in a WWE ring. A perfect example of this is David Hasselhoff, an actor who became famous in the '80s on Knight Rider, and in the '90s on Baywatch. Hasselhoff has made a couple of appearances in WWE (usually accompanied by The Bella Twins), but it always seems like the appearances are specifically tailored to what Hasselhoff wants to do. The TV legend never goes outside of his comfort zone, and his appearances are always short and easy. There have been multiple reported incidents of Hasselhoff's diva attitude (pun intended), so it would not surprise me if he views his appearances in WWE as something of a burden.
3 Loved - Pete Rose
None of the other entries on this list would have been possible if it weren't for Pete Rose. Best known as baseball's all-time hits leader, Rose has been denied his spot in the Baseball Hall of Fame because he admitted to betting on games while he was an MLB manager. Due to his popularity among sports fans, however, Vince McMahon asked Rose to make a guest appearance on WWE. Rose was absolutely pummeled by Kane, and the rest is history. The Rose-Kane storyline became an annual sketch, and in 2004, Pete became the first celebrity member of the WWE Hall of Fame. For Rose, being elected to the wrestling Hall of Fame had to be bittersweet after he was denied his place in the Baseball HOF, but he has consistently stated that he felt honored to be included by the WWE.
2 Regret - Hugh Jackman
As someone who used to watch WWE, I bet that movie star Hugh Jackman actually enjoyed his brief stint with the WWE. Jackman finds himself on this portion of our list, however, because of the circumstances in which he found himself performing for WWE. Jackman was involved in a short storyline in 2011 with Dolph Ziggler and Zack Ryder as part of a marketing campaign for the film Real Steel. Therefore, Jackman's biggest regret about his time with WWE is probably that he spent that time advertising such a terrible movie. Real Steel has a pretty cool premise (a robot fighting league controlled by humans), but the plot never managed to get off the ground. For an action star like Jackman, this film has to be considered as one of his greatest failures, thus hanging a shadow over his time with WWE.
1 Loved - Arnold Schwarzenegger
For the celebrities who grew up with WWE, the greatest honor they could hope for with WWE would be a chance to hold up the company's illustrious World Title. I'm not sure how much professional wrestling Arnold Schwarzenegger got to watch while growing up in Austria, but you can't fake the joy on his face when he got a chance to hold WWE's biggest prize. If you need more evidence of the Terminator's affinity for the WWE, look no further than his friendship with WWE Superstar Triple H, which has spanned over two decades. Their careers have actually paralleled in many ways, with Schwarzenegger making the transition from action star to national politician, and Triple H making the transition from wrestling talent to WWE executive.
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