Charlie Sheen has always been a magnet for outrageous stories, but his latest tale might top them all, a throwback to the mid-1980s when he and his father, actor Martin Sheen, faced off against none other than Michael Jordan.
On Jesse Watters Primetime, Sheen revealed how a casual day on the court turned into a once-in-a-lifetime memory.
“We did beat him fair and square in a two-on-one, because you can’t cover two people. It was me and my dad. Years later, I did a couple of Heinz commercials with him, and we were doing a behind-the-scenes interview together.”
“I brought it up, asked if he still held any resentment about me and my dad beating him back in ’85 or ’86. He looked right at me and said, ‘That never happened.’ He literally said it never happened.”
“I said, ‘Michael, you know the whole thing happened.’ And he just shook it off and said, ‘It doesn’t matter.’”
The showdown wasn’t just a simple pickup game, it was a three-part contest that tested Jordan against the Sheens in different ways.
The first event was a free-throw competition, but with a twist: Jordan had to shoot blindfolded. Even handicapped, MJ hit 11 out of 20 attempts. Charlie followed with a sharp 8-for-10, and Martin Sheen cleaned up the rest by sinking four. Against all odds, the Sheens stole the opener.
Jordan wasn’t about to let Hollywood actors show him up for long. In the second challenge a game of HORSE, he dismantled the Sheens with ease. His creativity and range left them chasing shots they couldn’t hope to replicate.
The final round was a two-on-one matchup, with the Sheens getting a five-point head start. Somehow, they made it count. Scrapping for every possession and leaning on teamwork, Charlie and Martin edged Jordan 10–5. It was the stuff of family legend, though Jordan has chosen to erase the result from his own memory.
But Sheen’s relationship with Jordan didn’t end there. Years later, during one of the darkest stretches of his life, Jordan’s greatness provided an unlikely turning point. In 1998, while Sheen was in a drug rehabilitation hospital, he begged to watch Game 6 of the NBA Finals Bulls versus Jazz, the night Jordan hit his iconic game-winner.
For Sheen, Jordan wasn’t just an opponent in a quirky backyard game. He became a symbol of resilience and excellence, someone who left a mark far beyond the court. And while MJ might laugh off that long-ago loss, Sheen will never forget the day he and his dad beat basketball’s greatest or the night Jordan unknowingly helped him find a reason to fight for himself.
It’s the kind of story that blends comedy, tragedy, and inspiration, perfectly in line with Sheen’s unpredictable legacy and now immortalized for audiences in aka Charlie Sheen.
A Hollywood wild card and an NBA icon, crossing paths in ways neither could have scripted. Classic Charlie Sheen, with Michael Jordan playing the straight man.
