As an actor, Winter spent many years on Broadway with supporting roles in productions of The King & I, Peter Pan, or The Boy Who Wouldn't Grow Up, and the American premiere of Simon Gray's Close of Play at the Manhattan Theater Club. After completing NYU film school, he and Tom Stern moved out to Hollywood, where the two wrote and directed a number of short films and music videos. Winter continued to find work as an actor, landing major roles in such big productions as The Lost Boys and Rosalie Goes Shopping. In 1989, Winter found international success when he co-starred with Keanu Reeves as Bill S. Preston in the smash-hit comedy Bill & Ted's Excellent Adventure and its 1991 sequel, Bill & Ted's Bogus Journey.
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