Alex Winter was born in Britain but became a child actor after he and his family moved to the United States. His first significant role was as a guest appearance on ‘Miami Vice’ playing a teen who idolised Don Johnson’s character.
Alex studied drama at New York University. He met many industry contacts, including writers from Saturday Night Live and Columbia Tri-Star Pictures, before travelling back to England to study at The Royal Academy of Dramatic ArtRADA). He returned to America in 1989, where he was offered the role of Bill S. Preston Esquire opposite fellow newcomer Keanu Reeves as Ted “Theodore” Logan in ‘Bill & Ted’s Excellent Adventure’.
The film received mostly positive critical acclaim and grossed over $40 million worldwide. The same year, Alex appeared opposite Will Wheaton in ‘The Wizard’ – a modern-day L. Frank Baum classic novella of “The Wonderful Wizard of Oz”. It grossed $19 million at the box office but wasn’t popular with critics or fans alike (it currently has a 7% rating on Rotten Tomatoes).
The following year, Alex returned for the sequel to his first major movie role, playing Bill S. Preston, Esquire once again opposite Keanu Reeves as Ted “Theodore” Logan in ‘Bill & Ted’s Bogus Journey.
It was a box office hit grossing over $40 million against a budget of only $10 million. The film received mixed reviews, but most critics praised Alex’s acting, with some calling his role the most memorable in the movie.
Eventually he won his first starring film role opposite Henry Rollins as Winterspeak in ‘Freaked’.
After these movies, Alex moved away from acting to pursue a career behind the camera instead. His first job was as an assistant editor on the Arnold Schwarzenegger action-comedy ‘Last Action Hero’, where he worked alongside many major industry contacts such as writers from The Simpsons and Terminator 2: Judgement Day. He also appeared briefly in Mike Judge’s cult classic comedy ‘Office Space’ as an unnamed worker at Initech.
Shortly after, he began working for George Lucas – helping to develop special effects technology for ‘The Young Indiana Jones Chronicles. It was here that Alex met director Tom Stern with whom he would co-found the production company St. Clare Entertainment. He then produced and directed his independent film, ‘Freeloaders’.
His directing career was short-lived due to legal problems with the movie; it didn’t receive a general release in theatres or home video, leaving many fans disappointed (it currently has no rating on Rotten Tomatoes). For this role, Winter received three nominations at the 1994 Sundance Film Festival – winning one of them. Despite not receiving a theatrical or home video release, the movie was aired on Showtime in the United States and various other channels worldwide.
Alex Winter has remained out of the public eye for the most part since then. Still, he occasionally appears as a guest speaker or panellist at various film festivals and technology conferences. In an interview with The Verge in 2016, he mentioned that he is currently working on a “spiritual successor” to ‘Freeloaders’ which is still in very early development – little else is known about the project.
Fans of Bill & Ted’s Excellent Adventure were also excited to see Alex pair up again with Keanu Reeves in the 2020 film “Bill & Ted Face The Music”
A lot has changed since the 1980s. Alex Winter, also known as Bill S. Preston Esquire on “Bill & Ted’s Excellent Adventures” fame; is now a director of films like “Freaks and Geeks” (1999) and “Fever Pitch” (2005). He had some acting roles in recent years too, but he said he prefers to focus more on directing these days.
