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 2012, he was then touring the country performing at comedy clubs and colleges. In 2013, he was cast in MTV2's Guy Code and writing, producing, and starring in his own pilots. In 2014, he starred in Friends of the People which lasted two seasons on TruTV. In 2015, Jermaine produced and starred in his debut comedy special, "Give 'Em Hell, Kid", that he licensed to Showtime.
On September 17, 2017, Fowler was the announcer of the 69th Annual Primetime Emmy Awards.
