Henton is an avid Cleveland Browns fan, as noted on the television series, Living Single. Henton never entertained the thought of a career in comedy. In 1982, while working during the day and studying computer science at night, Henton was urged by a co-worker to try his jokes at a local comedy club’s amateur night. By his second night, Henton won the amateur night contest and began stand-up part-time. Henton made the move to Los Angeles in 1985 and by 1988, started his stand-up career full-time.

After taking his comedy on the road for a year and winning the 1991 Johnny Walker National Comedy Search, Henton was spotted by The Tonight Show Starring Johnny Carson comedy executive Jim McCawley, who booked him for a performance on the show. As he finished his set, Henton looked to Carson for his approval and received much more. Henton was called over to take a seat on the coveted couch where Carson asked him if he had an agent. To Henton’s reply of "no", Carson mugged, "Well you will after tonight." It was a performance which Henton says gave his career a "serious jump-start."

In September 2000 Henton was involved in a serious car accident that "destroyed his left eye socket, shattered both of his legs, broke nine teeth and ripped up his stomach." The actor's face was badly deformed by the incident, though extensive plastic surgery restored most of his facial structure.