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When Starrcast II -- the four-day wrestling convention that coincides with All Elite Wrestling's pay-per-view debut of Double or Nothing on May 25 -- was looking for a headlining act, founder Conrad Thompson knew he needed a name big enough to match the glitz and glamour of the event's location in Las Vegas. 

"Well, I wanted to turn the volume up, and we are here at Caesar's Palace, and there is no bigger name in the history of wrestling than Ric Flair," Thompson told CBS Sports. "So, the 'The Roast of Ric Flair' is happening."

On Friday, May 24 at 9 p.m. ET from the Pro Wrestling Tees Theater inside Caesar's Palace (and live streaming at STARRCASTonFITE.com), "The Roast of Ric Flair" will unite some of the biggest names in pro wrestling and stand-up comedy, along with a few surprise guests to boot.  

If you're wondering whether Flair is ready for the type of no-holds-barred comedy that he will be victim of, the 70-year-old icon and 16-time world champion told CBS Sports he is both prepared and excited. He also was quick to point out how familiar he is with Sin City, the site of some of the most memorable outside-the-ring escapades of his legendary 40-year pro wrestling career. 

"I've got a lot of history with Caesar's Palace. Oh God, it was a regular stop in the 80s and 90s," Flair said. "I'm lucky to be here and every day is a blessing. But one of those reasons is Las Vegas. I've had a couple of drinks in that town!"

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Thompson's initial idea to roast Flair came in September 2018 ahead of the inaugural Starrcast, originally expected to be a one-and-done event in Chicago during the independent wrestling smash PPV All In weekend. Flair, however, was pre-booked for an event in Atlanta, so Thompson subbed in his podcast partner and longtime WWE creative member Bruce Prichard for what amounted to a successful practice run.

The Prichard roast included appearances by comedians like Ron Funches, Shuli Egar ("Howard Stern Show") and James Mattern, along with well-known wrestling names like Eric Bischoff, Sean Waltman and Jeff Jarrett. Many of the same names will return this year for Flair, including Funches, the host and roast master who wore a Flair-inspired robe during his recent Comedy Central special (which featured a cameo from Flair). 

"There is going to be a handful of wrestling people there, but Ric sort of transcends pop culture, so we are going to have more mainstream roasters from outside the wrestling sector," Thompson said. "The comedians are itching for the chance to carve up not just Ric but our dais as well. We are excited to have some fun, but some of these guys, they are not going for laughs. They are going for gasps."

The format will be very similar to popular roasts seen on Comedy Central and will feature what Thompson calls "a who's who of stand-up comedians" like Dan Soder ("Billions"), Taylor Williamson ("America's Got Talent"), Mike Lawrence (Comedy Central's "Roast Battle") and Dan St. Germain. 

"We will also have a whole host of wrestling names, whether it's people from Ric's past like Ricky Steamboat, probably his favorite opponent, or Jim Ross, who called some of his more iconic matches," Thompson said. "And a whole bunch of surprises. Whether you are a wrestling fan or not, there will be names you will recognize because everyone wants to come out and pay tribute to one of the greatest of all time."


A mortgage adviser and pro wrestling superfan by day, Thompson saw his chance friendship with Flair quickly turn into a podcasting co-host gig and eventually a spot in the family after he married Flair's oldest daughter Megan last year. 

In between, Thompson embarked on a meteoric rise within the crowded pro wrestling podcast space that saw him separate himself above the fold through wildly popular spinoff shows he created alongside well-known wrestling personalities Prichard ("Something to Wrestle With"), Bischoff ("83 Weeks") and Tony Schiavone ("What Happened When?"). That empire has grown to a fourth show expected to launch in the coming weeks titled "Grilling JR" with WWE Hall of Fame broadcaster and recent AEW signee Ross. 

"Conrad is probably one of the most innovative people I've ever met in my life," Flair said. "He has been so successful actually starting at the lowest position possible in a [mortgage] company that he now owns. To be able to come out and start a whole new empire, he has revolutionized the podcast world already."

Flair has been so open about the wild and extravagant life in his younger days, with much of his exploits achieving mythical status, that he doesn't expect there to be any stories shared at the roast that embarrass him. Thompson, for fear of such an event, did ask Flair ahead of time whether any topics were off limits, to which Flair laughed and replied, "Would it matter?"

The truth is, when it comes to the cutthroat format of a roast, nothing typically is out of bounds. From Flair's standpoint, the only thing he is worried about is how many stories will surface that aren't true. 

"Ninety-five percent [are probably true], I'll give you that. The problem is there have been too many stories," Flair said. "People love to tell stories that never happened, on top of the good and bad. I've got sisters, cousins, relatives all over the world according to people."

Flair, whose daughter Charlotte made history on April 7 by joining Ronda Rousey and Becky Lynch as the first females to main event WrestleMania, is largely still linked with WWE through his legends contract and sporadic television appearances. He also played a part in the recent Triple H-Batista feud that culminated in a match at WrestleMania 35, which ended with Flair running out to the ring to assist Triple H by tossing his protege a sledgehammer. 

"Oh, I had a blade on [me]! " Flair joked when asked whether he would have bumped or bled at age 70 if called upon. "Just kidding. But you know what Shawn Michaels said to me? They thought another mark was hitting the ring like the night before with Bret Hart [at the WWE Hall of Fame ceremony]. Shawn almost had to superkick me from the announce table."

Flair was also smitten with seeing Charlotte arrive to MetLife Stadium via helicopter in a callback to his own iconic entrance at the inaugural Great American Bash in 1985 before his NWA heavyweight title match against Nikita Koloff at American Legion Memorial Stadium in Charlotte, North Carolina.

"I probably cried the whole week, I've been crying since it first came about," Flair said. "I'm so thankful to WWE, from Vince [McMahon] to Hunter [Paul Levesque] and Stephanie [McMahon] and all the powers-that-be who put that together and taking that step forward with the woman. For me, I've used the expression about passing the torch, but my daughter just took the torch from me years ago. She is so good but she is just getting going. She has only been in the business for six years, which is hard to believe. The thing about her that separates her from a lot of people is that she's never satisfied with a performance. I was really proud and I'm proud of WWE for taking that step forward because they deserve it."  

Despite his obvious WWE ties, Flair was a product of the final days of the NWA territory system during his prime and later jumped ship between WCW and then-WWF during the 1990s and the peak of the "Monday Night Wars." Because of that, he has plenty of respect for what AEW is attempting to do by launching the same weekend as his roast. 

"I'm old school, so I think anytime there is an opportunity for guys to work who are qualified and have been trained properly in a position to be somewhat successful in their attempt to work for either company, I'm all about that," Flair said. "I think that's great. I don't think [AEW] should focus on the competition [with WWE] as much as just developing their own product. Their success will come from that. 

"The word competition is great. People love that part of time in the world, but this will be the first time someone with the kind of money that [Jacksonville Jaguars co-owner] Tony [Khan] brings. You know who Tony Khan is? Tony Khan is a sophisticated, intelligent, well-bred 'Nature Boy' Ric Flair with money. Tony Khan is the limousine-riding, jet-flying, kiss-stealing, bringing the hottest chick to every party that I go to with him, son of a gun. Now that he has the joint over in England [as co-owner of the Premier League team Fulham FC], I'm sure he has kissed girls all over the world and made them cry. If I had Tony's bankroll in the '80s, who knows where I would have been."

Flair also has a ton of respect for Cody Rhodes, the son of arguably his most iconic pro wrestling rival Dusty Rhodes, who joined forces with the likes of The Young Bucks and Kenny Omega to charter new ground in independent wrestling by creating All In and turning it into a new promotion with AEW.  

"It was a magical time in life when his dad and I were working together," Flair said. "People ask me all the time who was my best opponent and they think of Steamboat and Sting, but when I look back on my career, the run I had with Dusty was 20 or 25 years. At worst, we agreed to disagree, but he was a genius and I think he finally got the recognition that he deserves for being as creative as he was from Starrcade to the War Games to the Last Tango in Tampa with him and Harley [Race]. He was so far ahead of his time that I think I would put Dusty, in terms of creativity, right along with Vince [McMahon]. 

"Cody is a great performer and I'm happy that he landed where he has landed on his feet like this. It takes someone with a lot of courage and not just motivation. But to generally take that step forward on your own and be prepared to put yourself in a position where you might not be the most popular guy in the world but you are determined to make something work. It takes a hell of a man. That's my take on Cody."

Starrcast II is available for pre-order as a Weekend Pass with access to over 40 hours of content for $59 at STARRCASTonFITE.com. Single-day passes can also be purchased for "The Roast of Ric Flair" and other events.