Jon Stewart, Stephen Amell and the Anatomy of Ideal WWE Celebrity Crossovers

In Jon Stewart and Stephen Amell, SummerSlam welcomes a wisecracker and a dapper hero from outside the WWE world, two men who have successfully made the jump from celebrity to squared-circle participant. 

WWE's longstanding love of celebrities has seen the company welcome everyone from Muhammad Ali to Hugh Jackman to the ring. The results have varied. At times, everything clicks, and the actor, athlete or musician brings buzz and elevates the product.

When it doesn't work, though, the stench of failure wafts through the screen.

What made Muhammad Ali the right fit and Jeremy Piven a flop? Reflecting on past hits and misses reveals the formula for successful celebrity WWE stints: a mix of fandom, the right role and relevance.

Stewart nails all three requirements. He clearly appreciates being asked to step between the ropes. WWE is putting him in a position to succeed.

And unlike so many guest stars who have appeared on Raw, his celebrity is not marginal.

Name Power

Infusing celebrities into the WWE product is largely about attracting added eyes. It's a way to garner more mainstream attention and hopefully entice some curious new fans.

WrestleMania was built around that concept. Vince McMahon brought in Mr. T, Cyndi Lauper, Liberace, The Rockettes and New York Yankees manager Billy Martin to signal just how big a show the first edition of that event was.

A big key to making that marriage of wrestling and celebrity work in 1983 was timing.

Bringing in Lauper today wouldn't mean much. A Mr. T match in the 2000s would have had little impact. At the time, though, Lauper and Mr. T were red hot. And so WWE benefited from the buzz they created.

The same was true for Mike Tyson at WrestleMania XIV.

Tyson isn't just known to boxing fans; he's a transcendent star. In 1998, his name had plenty of weight. In part, that was thanks to his accomplishments in the boxing ring. Controversy made him a celebrity beyond that, though.

When Tyson knocked out Shawn Michaels at WrestleMania, it was less than a year after Tyson bit off a chunk of Evander Holyfield's ear. 

Compare the level of his fame then to some of WWE's D-list invitees and the contrast is stark. The Real Housewives of Atlanta star NeNe Leakes, for example, is the kind of celebrity who made a good number of fans ask, "Wait, who is that?"

WWE invited Grumpy Cat, Hoda Kotb and Mark Feuerstein to Raw as well. Their appearances won't make any "best of Raw" collection; they were largely forgettable. Bringing in someone at this level of renown makes it feel like the company is trying to cash in on something that's already died down and/or wasn't that big in the first place.

This is Amell's biggest flaw as a WWE performer. He's simply not a huge name. Arrow is popular, but Amell isn't Mr. T in the '80s. What makes up for that is that he reaches WWE's key demographic: young males.

On the other hand, there is such little overlap between Leakes' fanbase and the WWE faithful. 

A Fan of the Business

It's not just enough to be well-known in order to be fit for the WWE ring, though. There has to be mutual interest. The best celebrities approach their roles on WWE TV earnestly and passionately, partly because they are fans who are thrilled to be there.

Ali respected the craft and even modeled his persona after Gorgeous George. 

He was a big fan of George's. He watched how the heel would rile up the crowd and looked to emulate much of his style. As John Capouya recalled in Gorgeous George: The Outrageous Bad-Boy Wrestler Who Created American Pop Culture, the legendary heavyweight said of the flamboyant heel, "I saw 15,000 people comin' to see this man get beat. And his talking did it. I said, 'This is a good idea!'"

Angelo Dundee talked about The Human Orchid's influence on Ali in bonus footage from ESPN's Muhammad and Larry:

And so it's no surprise that when WWE invited Ali to clash with Gorilla Monsoon in 1976, the spot was a hit. Ali approached this endeavor seriously.

Years later, in a much less physical role, Stewart had the same mindset.

The former host of The Daily Show is a vocal fan of WWE. He has mentioned storylines and shocking developments from that world on his show, even when the audience went silent afterward.

His appreciation for what the WWE Superstars do was clear when he was a part of the action earlier this year. After Seth Rollins had popped up on his show, Stewart confronted him on Raw.

Stewart's performance was powerful. He took this opportunity seriously and seemed to pour the same amount of heart into it as he did his own show.

There was no tongue-in-cheek element to any of it. There was no snickering on stage. 

Amell followed Stewart's lead when he brawled with Stardust and later went to Triple H to demand a match at SummerSlam.

Former WWE writer Alex Greenfield pointed out why Amell succeeded that night:

The opposite was true when Sean Hayes, of Will & Grace fame, guest-starred on Raw to promote the new Three Stooges movie. The segment didn't work because it felt like a cheap shill, and the WWE fanbase didn't care about Hayes or his costars.

It certainly didn't help that Hayes clearly doesn't think much of WWE. When he appeared on Conan to talk about his experience, he mocked it, sarcastically calling it "quality television." 

Both Amell and Stewart don't share this dismissive attitude. They have made it clear that they admire the wrestling craft as fans. It's then up to the writing team to find them an entry point into the WWE landscape. 

Finding the Right Part on the Stage

A celebrity's level of involvement and physical gifts have to match.

David Arquette would have been fine as a ring announcer, referee or someone's manager. He never should have been in the ring, and he most certainly never should have won the WCW world title.

Credit: WWE.com

Fans still cringe at the thought of him holding up the gold because his presence disrupted the logic of the wrestling world. No matter how one scripts it, a skinny non-wrestler should not be getting over any of the gladiators of the ring.

WWE seems to understand that with both Stewart and Amell. 

Stewart's role will be telling jokes and interacting with wrestlers backstage, as it should. Amell, who is much more athletic and more believable as a competitor, will get into the ring, but with a caveat.

WWE wisely is having Neville share the in-ring load with him as well. To have Amell wrestle a singles match or win a championship a la Arquette would be taking things too far.

Credit: WWE.com

Amell is athletic enough and looks the part to the point that it's believable that he could hang in the ring with Neville's help. That hasn't been the case for past celebrities. 

It made sense for a Tyson right hand to knock The Heartbreak Kid flat on his back. The boxer is one of the most feared competitors to ever put on a pair of gloves. Jon Heder, on the other hand, shouldn't have been allowed in the ring, even if it was just briefly.

And WCW jumped the shark by having Jay Leno not only compete at Road Wild 1998 but headline it and get the deciding pin.

Avoiding that kind of misguided choice gives celebrities a chance to succeed. Stewart's not going to throw any forearms at SummerSlam or hoist up the Intercontinental Championship by the end of the night; he's just going to provide comic relief and, hopefully for WWE, increased viewership.