While in high-school, Radnor High, he was involved in dramatic arts, president of the debate team and tuba player in the high-school band. Wilson's first 'real' stage experiences were as a standup comedian, while studying at the American Academy of Dramatic Arts.

His breakthrough is considered to be: Back to the Future (1985) (which was later renamed Back to the Future: Part I, when two sequels were released). In that movie he played the menace to society: Biff Tannen. Wilson's talents as a comedian and an actor combined to make Biff a character people loved to hate. When Back to the Future became a trilogy, he was naturally asked to perform in these sequels too as Biff, Biff's grandon Griff and the great-great-grandfather Buford 'Mad Dog' Tannen.

He later went to co-star in a CD-ROM computer game, with Mark Hamill. This game called: Wing Commander III: Heart of the Tiger (1994), would later on be part of "The Wing Commander Series". It was extremely popular at the time. In the game Wilson played Major Todd "Maniac" Marshall, one of the pilots of a starship under fire. In this game his character again is very unpopular. He also starred in the sequel to that game "Wing Commander IV: The Price of Freedom", which was even hailed more then its predecessor and is considered by some to be a classic computer game.