From a TV special to an annual celebrity tradition, Kenny Rogers’ ranch was once a melting pot for celebrities. The Kenny Rogers Classic Weekend was the highlight of many celebrity calendars for three years in the ’90s. The Gambler hosted professional athletes, musicians, and Hollywood A-listers on a 1200-acre property for a day of competition like golf, basketball, and fishing. But it was really about seeing our favorite celebrities cross over. Like watching the icon shoot hoops with Michael Jordan, Larry Bird, Dominique Wilkins, and Charles Barkley. It was also fun to see Chuck and MJ enjoy their favorite pastime of golf years before their friendship fizzled.

These TV specials had some of the most unfiltered celebrity moments. Like when they pranked each other. It was golf legend Tim Simpson and his son who got Charles Barkley in one epic prank during one of these weekends at Beaver Dam Farms, as narrated in Rogers’ 2011 memoir Luck or Something Like It: A Memoir.

Simpson’s son, Chris, slipped a frog inside the pocket of Barkley’s workout pants. Simpson very hilariously described the Chuckster’s reaction to it, “And I tell you what, Charles lost it,” he said as per the New York Times. Too bad it wasn’t aired on TV because, according to the golfer, “I mean, you would’ve thought he put a rattlesnake in his pocket. It was hilarious.”

That was just one of the fun shenanigans Chuck was up to at Rogers’ ranch. He’d make and lose a variety of bets to MJ. And the Chuck’s fun memories with Rogers were not limited to the Kenny Rogers Classic.

Charles Barkley and Kenny Rogers’ friendship

Charles Barkley’s love for country music (besides Beyonce) is more than just a running joke on Inside the NBA. Since joining Instagram, he’s made friends with many country artists as if his social circle didn’t already have some legends in the genre like Kenny Rogers. Sir Charles even scored Rogers seats to the 1993 NBA Finals to see his Phoenix Suns lose to Jordan-led Chicago Bulls, Rogers wrote in the memoir.

They had other funny moments like Rogers mixing up his father-in-law, also named Charles’ contact with Barkley’s. He called Chuck instead of his father-in-law but Barkley didn’t know at the time. Kenny played it off like he meant to call him and casually informed Chuck he’d call him back soon. Barkley was none the wiser.

When Rogers passed away in 2020, Chuck was not on any public platform to comment on his old friend. All we can do is wait for Barkley to narrate more of his tales with Rogers.

Stay tuned for more such updates, and to follow what Shaq’s ex-agent, Leonard Armato, has to say about the infamous Shaq-Kobe feud, Caitlin Clark’s Olympic snub, and more, watch this video.