Actor Charlie Sheen has never been one to mince words, and when it comes to basketball’s greatest player debate, his answer left no room for hesitation. Appearing on the All The Smoke podcast with Matt Barnes and Stephen Jackson, the Hollywood star was asked to pick the GOAT between Michael Jordan, Kobe Bryant, and LeBron James, and his response was His Airness.
“I mean, why is there even a debate? It just feels kind of obvious, right? I’m sure LeBron won’t appreciate that.”
When pressed to rank the trio, Sheen didn’t hesitate.
“The order you just presented them,” he replied, confirming his list as Michael Jordan first, Kobe Bryant second, and LeBron James third.
For Sheen, it wasn’t just a casual opinion thrown into the endless GOAT conversation; his admiration for Jordan runs deep, rooted in a personal connection that dates back nearly four decades. In the mid-1980s, long before Two and a Half Men or his infamous ‘winning’ era, Sheen and his father, actor Martin Sheen, found themselves on the same basketball court as a young Michael Jordan. What followed was one of the most bizarre and unforgettable celebrity-athlete stories ever told.
As Sheen recounted earlier this year, the father-son duo actually beat Jordan in a two-on-one game back in 1985. The day was part pickup game, part mini-competition. First came a blindfolded free-throw contest, where Jordan hit 11 of 20 attempts, but the Sheens collectively outscored him.
Then came a game of HORSE, where Jordan predictably dismantled them with trick shots and impossible fadeaways. But in the deciding two-on-one matchup with a five-point head start, the Sheens somehow pulled off the upset, winning 10–5.
Jordan, according to Sheen, refused to ever acknowledge the loss.
Years later, the connection between Sheen and Jordan came full circle in a far more serious moment. In 1998, while Sheen was in rehab battling addiction, he pleaded with staff to let him watch Game 6 of the NBA Finals, the night Jordan hit his iconic jumper over Bryon Russell to clinch his sixth championship. For Sheen, that game wasn’t just entertainment; it became a moment of inspiration.
That lifelong reverence explains why, when Sheen says there’s no debate, he means it. To him, Jordan isn’t just a basketball legend, he’s the embodiment of discipline and dominance, someone whose aura transcended the game.
Coming from Charlie Sheen, an icon of chaos, confidence, and charisma, his GOAT choice feels fitting. For him, Michael Jordan isn’t up for debate. He’s simply ‘obvious.’
