At age 20, he moved to New York City from Maryland. By day, he job searched and by night he was performing at local open mics in Times Square. In 2013, he was cast in MTV2’s Guy Code and writing, producing, and starring in his own pilots. In 2015, Jermaine produced and starred in his debut comedy special, “Give ‘Em Hell, Kid”, that he licensed to Showtime. In 2017, Fowler became an executive producer and star of Superior Donuts on CBS.