He formerly wrote for The Daily Show on Comedy Central and Any Given Wednesday with Bill Simmons on HBO. Free won an Emmy Award for his work on the Daily Show in 2015. He is a former college basketball player.
Free grew up with his mother and grandmother in Compton, California. He attended Dominguez High School, where he played basketball. In 2002, the Los Angeles Times called him the "team's best player". He chose to remain local and decided to play college basketball for the Long Beach State 49ers. Their program was struggling, and Free liked his chances of earning a starting role. Injuries sapped his dream of playing professionally in the National Basketball Association (NBA), and he had no interest in playing overseas. While he was out injured with a torn meniscus in his right knee that required surgery, he entertained the team with his humor, which was a prelude to his career in comedy. While in college, Free took a Comedy Writing class and performed at Laugh Factory in Hollywood and The Ice House Club in Pasadena, California.
Free began writing for The Daily Show in October 2012. After coming in second place in a contest to win a position working for the show, he was invited by Executive Producer Rory Albanese to tour the show's set, which Free treated as a consolation prize. During his visit, he was surprised backstage when Jon Stewart offered him a full-time writing job. Free won a Primetime Emmy Award for Outstanding Writing for a Variety Series on The Daily Show in 2015 after being nominated in the two years prior. He has also had recurring roles on the shows Tosh.0 and Chelsea Lately. In 2016, Free wrote on the HBO show Any Given Wednesday. In 2017, Free was hired as a writer for Full Frontal with Samantha Bee. In November 2018, he publicly apologized for old tweets that had been criticized as offensive, in particular anti-semitic.
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