[5] Growing up with his mother and grandmother in Compton, California,[1] Free attended Dominguez High School, where he played basketball; in 2002, the Los Angeles Times called him the "team's best player".
[8] In college, Free took a comedy writing class and performed at Laugh Factory in Hollywood and The Ice House Club in Pasadena, California.
[17][18] In November 2018, after a series of anti-Semitic tweets from 2010 and 2011 were discovered in Free's Twitter feed, HBO said that the company had no plans to work with him in the future and stated that "This kind of language is deeply offensive and inexcusable."
"[19] Controversy emerged in April 2021, after Cynthia Kao posted a video on the social media site TikTok, alleging that Free's Two Distant Strangers was plagiarized from a comedy sketch she had directed in December 2016 titled Groundhog Day For a Black Man.
Furthermore, in 2020, during the George Floyd protests, social media news outlet NowThis contacted Kao about featuring the film on their Facebook and Instagram pages.