His mother, Gregg Mayer, is a New York-born dancer who trained with Martha Graham, and founded a modern-dance company in London in the mid-1960s.

[14] As an actor, Winter spent many years on Broadway with supporting roles in productions of The King and I, Peter Pan, and the American premiere of Simon Gray's Close of Play at the Manhattan Theatre Club.

Winter continued to find work as an actor, landing notable roles in such big productions as The Lost Boys[2] and Rosalie Goes Shopping.

[16] In 1989, Winter found international success when he co-starred with Keanu Reeves, playing William "Bill" S. Preston Esq.

[17] Following the success of Bill & Ted, Winter and creative collaborators Tom Stern and Tim Burns were hired to develop a sketch comedy show for MTV.

He directed its sequel, Ben 10: Alien Swarm, which aired on Cartoon Network in November 2009 and captured over 16 million viewers in its premiere weekend.

As of 2008, he was attached to write the screenplay for the Howard Stern-produced remake of Rock 'n' Roll High School.

[20] Winter's 2012 VH1 rock doc Downloaded earned worldwide critical acclaim at theatrical and festival screenings.

In 2013, he had a role in the thriller Grand Piano, starring Elijah Wood and John Cusack, playing The Assistant.

[23][24] In July 2015, Winter began work on a biographical documentary of the rock guitarist and composer Frank Zappa.

He has criticized media companies and news outlets for exaggerating how many people used Napster for digital piracy.

[citation needed] Winter's interest in technology, the Internet and privacy inspired him to make the 2012 documentary film Downloaded, about internet file sharing and Napster, and the 2015 film Deep Web, about the Silk Road, bitcoin, and the dark web.

[36] On February 2, 2018, Winter revealed that he was molested by an older man at age 13 while acting on Broadway.