Comedian Tony Hinchcliffe has shared a story about a chaotic night out with Ric Flair, recalling events that took place around Flair’s appearance on Kill Tony.
Speaking on What’s Your Story? with Stephanie McMahon, Tony Hinchcliffe said Ric Flair invited him out the day before the show. What began as afternoon drinks quickly escalated into an all-night session that also included comedian Shane Gillis, rapper Wiz Khalifa, and a group of Southwest Airlines flight attendants.
Hinchcliffe said it became clear early on that the situation was getting out of hand, noting that the drinking started hours before the evening was meant to wind down. Despite that, Flair abruptly decided it was time to leave, only for the night to continue in increasingly unpredictable fashion.
According to Hinchcliffe, Flair arrived the following day already intoxicated and insisted on walking to the venue from his hotel, bringing along several people he had met the night before. Along the way, Hinchcliffe said Flair’s behaviour drew attention, including a moment that left him stunned as onlookers reacted with laughter and disbelief.
“He’s like, ‘I’m over at the Hilton. Come walk me over.’ And he’s got these Southwest flight attendants that he just met at the bar, and he wants to bring them to the show. They’re cracking up, having the time of their lives, and one of them goes, ‘Slap my ass again, Ric.’ And he does the loudest slap you’ve ever heard. Just WHAP. I’m sitting there thinking, ‘Oh my God, this is actually happening.’”
The situation became even more surreal when Hinchcliffe claimed Flair repeatedly insisted on keeping a bag with him at all times. When asked what was inside, Flair allegedly said it contained $200,000 in cash from autograph signings.
“He keeps saying, ‘I gotta keep this bag with me. I can’t lose this bag.’ And I go, ‘What’s in the bag?’ And he goes, ‘Two hundred thousand dollars cash.’”
Hinchcliffe described the entire experience as quintessentially Flair, painting a picture of the WWE Hall of Famer adorned with jewellery, wearing multiple Rolex watches, and carrying a bag of cash while preparing to appear on one of comedy’s biggest podcasts.
Despite the chaos, Hinchcliffe said he views the story as another chapter in Flair’s long-standing, larger-than-life reputation, adding that moments like this only reinforce the legend surrounding him.
“It’s the most Ric Flair thing ever. I love him. His legacy is unbelievable. This only helps it.”
When Did Ric Flair Start Wrestling?
Ric Flair began his professional wrestling career in 1972, following training under the legendary Verne Gagne at the AWA wrestling school in Minnesota. Flair’s career nearly ended just three years in as he was involved in a near-fatal plane crash in 1975, an event he has often credited with hardening his resolve to succeed in wrestling.
Early in his career, Flair worked across multiple territories, including the AWA, NWA, and, later, Jim Crockett Promotions, where he refined the flamboyant persona, marathon match style, and microphone confidence that would define his legacy. By the late 1970s, Flair had firmly established himself as one of wrestling’s rising stars, setting the stage for his emergence as the face of the NWA throughout the 1980s.
