Travon Free, standing at six feet seven inches tall, was initially set for a promising basketball career -- but that was before he became a two-time Emmy Award winner for his work on
The Daily Show with Jon Stewart
Full Frontal with Samantha Bee
. "Basically, I had hoop dreams, then those hoop dreams turned into Hollywood dreams after knee surgery," he says. While bonding with teammates, the Compton native discovered a latent comedic voice and started his new journey. The next few years would be dedicated to honing his writing and diving headfirst into stand-up.
Then, in 2012, the unthinkable happened: After submitting his work to
The Daily Show
, the writing room enlisted his wits, and, within a few years, the team was awash in Emmy nominations. His first award, for Outstanding Writing for a Variety Series, came in 2015, and he returned for a victory lap in the same category two years later after joining the
staff. "You're standing on that stage and all the biggest TV stars in the world are sitting right there. They're looking up at you and you're looking at them. You're like, Oh man! Viola Davis is looking at you right in the face right now!" he says. "Winning one time is cool, but then winning a second time, you're like, Oh, shit. I might actually know what I'm doing.''
After his Emmy wins, he feels he's at the pinnacle of his career, but reaching the top means more responsibility, and this time he's hoping it'll be on his own terms. With
Him or Her
, which boasted interest from HBO and early cosigner Issa Rae, Free plans to delve into the Black, bisexual male experience in a way television has never experienced before. "I'm only really interested in telling stories that I connect to on a deep level, and I knew I had this story that was about me, but it just didn't exist," he says.
Him or Her
, Free hopes to not only write about everything from bisexual erasure to dating, but also kill the stigma around different expressions of identity. "I definitely want to have a conversation around Black masculinity, and I want to explore it within the context of the Black community and the queer community," he says. "There's so many men who suffer from not being able to have this conversation because of what they've been taught, and I want to help reshape that conversation because I feel like there's a lot of people suffering."
Free notes that even though there's more visibility of Black folks and people of color in Hollywood than ever before -- name-dropping Rae, Lena Waithe, and Justin Simien -- there are still not enough voices being heard. "As far as queer representation, I think we've done incredibly well in the last 10-to-15 years when it comes to the L-G-T," he says. "We've done consistently poor with the B, and I'm trying to do everything I can to change that."
While Free continues to develop
Him or Her
, you better believe he's booked and busy. Last December, he wrapped up his first season on HBO's
, where he transitioned to writing in a more character-driven format than he had done in his previous work. Similarly, on Showtime's
, he paved new ground working on a period piece that required extensive research on the 1987 stock market crash. And, just beyond the horizon, you may see his name on the big screen. "Unfortunately, at the speed movies work, you won't see them next year," he demurs. "But there are a lot of really, really dope projects that people don't even know are being made."
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