Donald Faison Explains Why Leo DiCaprio And Tobey Maguire Didn’t Invite Him Back To Play Basketball

On one of this week’s episodes of Fake Doctors, Real Friends, Zach Braff and Donald Faison invited their old friend and former Scrubs cast mate, Ken Jenkins, onto the show. Jenkins played Dr. Kelso on the series, and he proved to be an unexpected delight on the episode, nothing like the more villainous Dr. Kelso of the first season of the sitcom, and everything like the more sweet-hearted version of Dr. Kelso, who kissed Laverne on the forehead on her deathbed, and who had his doctors backs’ when needed.

However, the more interesting part of the episode came when a fan was invited on to ask a couple of questions. Both were directed at Faison. In the first, Faison was asked who he thinks could have played Dr. Turk had he not landed the role, and if timing wasn’t an issue. Unsurprisingly, Faison said Dulé Hill — the West Wing star who had a similar Zach and J.D. dynamic with James Roday on the long-running Psych — but the other two possibilities were a little more surprising: Jaleel White (Urkel from Family Matters) “would have crushed that role,” as would have Damon Wayans, Jr., if he were older back then, Faison said. (Braff’s answer for who could play J.D., for the record, was Ben Platt).

However, the even more interesting part was when Faison spilled a little tea about playing basketball with longtime best friends, Leo DiCaprio and Tobey Maguire. As Faison tells it, he was in Miami when “Leo and Tobey invited me” to play basketball. “This was one of the biggest moments of my life,” Faison says on the podcast, because “as a young actor, to me, Leonardo DiCaprio is the best actor in the world … I don’t think that anyone is better than him when it comes to my peers, people my age.”

In Miami, the three play on the same team, “and we play against some Floridians in a 3-on-3 game, and we win. And I remember thinking, ‘I have arrived. I played ball with Leo. I played ball with Tobey. We were on the same team. It’s happening! I’m going to be in the next Spider-Man. I can feel it!”

“I was wrong,” Faison said, deflated.

Subsequent to their game in Miami, Leo and Tobey invited Faison out to play again at someone’s house, and this time, when Faison arrived, Maguire said, “I don’t want to be on his team. I won’t have any fun on his team.” It is worth noting, too, that Tobey Maguire has a reputation for being both very competitive and sometimes cruel, if one believes Molly Blooms’ book, Molly’s Game, about a regular celebrity poker game Molly Bloom created and that Tobey Maguire ultimately had a hand in destroying, but not before Maguire humiliated Bloom in front of Ben Affleck and others. (Bloom’s book was subsequently turned into a movie written and directed by Aaron Sorkin, where Michael Cera played the Maguire role).

Hearing that “I won’t have any fun on his team” naturally upset Faison, who had had such a good experience in Miami with him and DiCaprio. “I took offense to it … and I was like, ‘OK, fine.’ And I proceeded bust their ass on their court!”

“Aaaaaaand,” Faison added, “I never got invited back.”

“Yeah, you got to be not too good. That’s the trick to playing with fancy celebrities,” Braff said.

“Right,” Faison agreed. “You got to make it feel that they can compete on their level. You have to bring them up to your level. You have to be the LeBron James. You have to score buckets, but you have to make them feel like they’re doing their thing.”

And that was Faison’s brief flirtation at a friendship with the biggest A-list stars of the time.

Meanwhile, Faison did concede that he has been outplayed by a number of other celebrities on the basketball court, as well. When asked to name the best celebrities he’s played against, Faison name checks Michael B. Jordon, Brian McKnight, Jesse Williams, and James Lesure, the Good Girls star Faison believes may be the best he’s every played.

Source: Fake Doctors, Real Friends