“Michael Jordan Responds in 20 Seconds”: Charlie Sheen Describes His Relationship With MJ

Charlie Sheen’s Untold on Netflix has become a hit thanks to the insights it provides into his wild, eventful life and the challenges he faced on his road to fame. Sheen is on a media tour to promote the docuseries, and the NBA community has taken an interest, too. Sheen’s friendship with Michael Jordan was the hottest topic discussed during the Hollywood star’s appearance on the All The Smoke podcast.

The hosts of the show, Matt Barnes and Stephen Jackson, also had plenty of other questions for Sheen. They wanted to know what it was like to star in hit movies such as Platoon and Major League. But when basketball podcasters have a chance to get inside stories about Jordan, they rarely let it pass.

Sheen happily shared how his relationship with the Bulls legend began when he was randomly selected to play against Jordan in a basketball game on a TV show. “This opportunity just fell out of the sky,” he said.

There was this show, a short-lived show, pitting actors against athletes in their respective sports. And the card we drew was Jordan, and in a two-on-one,” Sheen added. “It was me and my dad. So, we were just like, sure, why not?”

Charlie, as well as his dad, actor Martin Sheen, were also massive sports fans. The two used to play basketball against each other when Charlie was a kid. So, they decided to take up the opportunity and make the most of it.

It may have been two-on-one, but it was still against an all-time great. Still, that day, Charlie was hot and shot the Sheens to victory. Jordan still denies to this day that it ever happened, despite it being on video.

Soon, Sheen started making enough money to start going to Jordan’s games for the Chicago Bulls. And their relationship only grew from there. 

“I would fly out to Bulls home games… Then we worked together on a commercial campaign. We did Hanes, we sold underwear together,” Sheen detailed. 

“There was a time when I would text him, and this dude would literally respond in like 15 or 20 seconds,” Sheen added.

It definitely would have been a pretty cool thing to brag about back then. But Sheen insisted he never did anything of the sort. He would only use that in very specific instances when his other friends weren’t answering his texts for a while.

“I never did it in front of people to show off, like, ‘Watch how quickly MJ gets back to me.’ But I was just like, Wow,” said Sheen.

“But I would use it like that’s now the bar. And I would tell my friends, ‘Dude, it’s been like 4 hours. Michael Jordan responds in 20 seconds.’ So, it was a valuable tool for me,” he joked.

It sounds like Charlie and Michael developed a genuine friendship and still keep in touch. Over time, though, Sheen drifted away from attending Bulls games and began following baseball more closely as a Cincinnati Reds fan. Of course, that moment playing against Jordan remains a pretty unforgettable memory for him.