44.Damon Wayans

One of the few examples that support the expression “like father, like son,” Damon Wayans is an actor and a comedian, which is also the career his junior eventually pursued. After his big break from the TV show In Living Color, the actor went on to work for films like Beverly Hills Cop, The Last Boy Scout, and My Wife and Kids.

Damon Wayans got widespread recognition for his roles in films and shows – he even earned a People’s Choice Award for Favorite Male Performer in a New TV Series for My Wife and Kids. However, there would be times the actor would also reward himself for his achievements, like the time Wayans bought himself a lovely Dodge Challenger Hellcat.