Travon Free tells Jalen Rose how he landed ‘The Daily Show’

It’s safe to say we are blessed with the comedy, filmmaking and intellect of this week’s “Renaissance Man” guest because of a torn meniscus. That’s right. A piece of damaged cartilage was the turning point that made former “The Daily Show” writer and recent Academy Award winner Travon Free go from hoops to words and reels.

“I went to Dominguez High, you know, I was teammates with Tyson Chandler and all these guys who went on to become like NBA stars,” he told me of the Compton, California, school. “And, you know, I had the same dreams and aspirations.”

He played Division I ball at Long Beach State.

“My sophomore year, I had knee surgery after I had just tied our school record for rebounds in a game … I was hoping for that type of [pro basketball] life,” he said. “And, you know, once I had knee surgery, I realized, that was the end of the road in terms of like that particular dream. It was when I made that hard pivot to writing and learning the craft of screenwriting, because I had loved writing my whole life, and I had always done it. And so my academic adviser was like, ‘I know you wanted to be a filmmaker when you got here and you couldn’t because of your basketball scholarship. So maybe now you have like a year off to rehab. You can take some time and take some of these classes.’ And it changed my life.”

Injuries can be crossroads for athletes, but not all take a positive view or path. But Travon, who stands 6-foot-7, stretched himself even further and showed his versatility. It turns out he was a good rebounder on the court, and in life.

He became a sponge trying to find his own style. His earliest influences were late rom-com queen Nora Ephron, Richard Curtis, Japanese legend Akira Kurosawa, Spike Lee, Quentin Tarantino and the late, great “Boyz n the Hood” director John Singleton.

First, he overcame his fear of stand-up, hitting the stage for the first time in college.

“You have to learn the skill of mastering different crowds. You have to learn how to talk to different people and talk to different audiences. And you also have to learn to be OK with that not going the way you want it to go,” he said. “And so what it is, is that exercise is an exercise in ego management and ego suppression, because your ego is the reason you’re up there.”

But his ego wasn’t so big when he landed his “The Daily Show” writing gig in 2012. He was 26. He didn’t even have representation. Travon heard about an opening and casually reached out to a writer on the show. They asked him to submit something, but he was terrified.

“I was just chillin’ in Inglewood in my apartment trying to, like, get a job. And I did a submission. And I initially came in second place to the girl who got the job, who got hired. But it was like a really close second, like so close that they didn’t want to not hire me. And so they ended up hiring me anyway,” he said. “And getting that job was such a big deal. And it was an interesting time because Jessica Williams had just gotten there, and we both were Long Beach State alumni. So you got two black kids from Long Beach State who grew up in the inner city of LA and are somehow both at the same time on this very prestigious political comedy show on Comedy Central. And it just felt special, man.”

Suddenly he was writing for the biggest comedy show and the biggest comedy star, Jon Stewart. And every possible door was open to him.

Travon Free attends the Lemonada Media launch party at Largo At The Coronet in 2019.
Travon Free started writing for “The Daily Show” in 2012.
Getty Images

“You get invited to everyone’s party. You get invited to everything in New York
because Jon Stewart is like the biggest thing happening in New York outside of ‘Saturday Night Live,’” he said. “And he’s the guy everybody wants at their party. He’s the guy everybody wants to talk to.”

But as life took a more serious turn during the pandemic and the wake of George Floyd protests, so did his art.

He made “Two Distant Strangers,” a short about a man stuck in a time loop, who has to relive an altercation with police over and over.

“It was a pandemic. George Floyd had been killed, Breonna Taylor [was] killed. And we were in the streets, man, like every day,” he said. “And we didn’t have nothing else to do but be out there and raising our voices.

“One day, this idea kind of just like crystallized in my mind of like, you know, seeing all those names and seeing, you know, every day at the end of the day on the news, watching the marches from around the world and feeling like every time a new name came up, you were reliving that same cycle of emotional feelings, of sadness and pain and hopelessness,” he said.

“And then eventually getting back to hopeful that got you back out there in the streets the next day,” he said comparing it to “Groundhog Day.”

It won an Academy Award for Best Live Action Short Film, and Travon, who is a big sneaker and fashion guy, was dressed by Dolce & Gabbana for the Oscars. As a fellow tall person, I can tell you, that it feels great when a designer creates something specifically for you. Because we can’t just go buy pants off the rack.

“It was perfect, and it was amazing. It feels so good to wear.” But he always has flavor. “It feels good to put on your favorite Jordans, to put on a nice suit, to go out and put on a nice jacket, blazer and some some nice jeans that you bought.”

Travon is also incredibly secure and open about being bisexual.

“I think I came out when I was 25,” he said, noting it was before gay marriage was legalized and corporations were flying the rainbow flag during Pride Month. “Now, when I was like going through that, it was not at all like [that]. It was very much the opposite. And so, I knew I was taking a level of risk in doing it, especially like being a college basketball player and all those things that go along with that.

“And it couldn’t have been a better decision because the amount of messages that I get from people that I’ve gotten over the last 10 or 12 years from parents, from kids, from like you name it like. It was things like, ‘I didn’t know until I saw your story. I didn’t believe that this thing was this until I heard you talk about it’ … Like that, to me, is invaluable,” he said, adding, “I’m black, I’m bi, I’m 6-foot-7. I’m a filmmaker, I’m a writer. Like, I’m all of these things everywhere I go. And I love representing all of those different communities.”

Another label he wears proudly is that of a Compton native. So I wanted to know five celebrities who best represent his hometown. And he just kept naming names like Bubba in “Forrest Gump” running through shrimp recipes.

Ava DuVernay, Kendrick Lamar, Tyson Chandler, Eazy-E, Venus and Serena Williams, Richard Sherman and Kevin Costner were on his long list. So if he ever gets sick of writing, making films and comedy, I would suggest official Compton historian and ambassador for his next calling.

Detroit native Jalen Rose is a member of the University of Michigan’s iconoclastic Fab Five, who shook up the college hoops world in the early ’90s. He played 13 seasons in the NBA, before transitioning into a media personality. Rose is currently an analyst for “NBA Countdown” and “Get Up,” and co-host of “Jalen & Jacoby.” He executive produced “The Fab Five” for ESPN’s “30 for 30” series, is the author of the best-selling book, “Got To Give the People What They Want,” a fashion tastemaker, and co-founded the Jalen Rose Leadership Academy, a public charter school in his hometown.