The comedian started his professional career in 2007, performing at different stands and clubs around Greensboro in North Carolina. After a while, he started featuring as an opening act for the popular comedian, Chris Wiles. To grow his popularity began to grow, he teamed up with comedians like Darren Brand and B-Daht to initiate a comedy show tagged Freestyle Funny Comedy Show in 2009. The trio was later joined by DeMar Rankin Sr. Along with the group, Chico Bean performed stand-up comedy in clubs, as well as colleges and universities.

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He got his breakthrough when Nick Cannon, who heard about his comedic performances, invited him to participate in his show, Fresh Faces of Comedy at the Gotham Comedy Club. Impressed with his outstanding performance, Nick further helped the upcoming star, Chico to audition for the MTV comedy show Wild ‘N Out. After winning the audition, Chico Bean joined the fifth season of the show and since then, has been one of the most prominent figures on the show to date. He has co-performed alongside other comic stars including Karlous Miller and rapper Safaree.