As an actor, Alex 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 dropped out of NYU film school before his senior year and moved to Hollywood, where he began to write and direct a number of short films and music videos. Winter continued to find work as an actor, making his feature film acting debut in the 1985 film Death Wish 3.
He would go on to have notable roles in productions such as The Lost Boys(1987) and Rosalie Goes Shopping (1989).
In 1989, Winter found international success when he co-starred with Keanu Reeves, playing William “Bill” S. Preston Esq. in the smash-hit comedy Bill & Ted’s Excellent Adventure, a role he reprised in the sequels, Bill & Ted’s Bogus Journey and Bill and Ted Face The Music.
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. The result, 1991’s The Idiot Box.
Winter, Stern and Burns accepted a deal from 20th Century Fox with Winter and Stern jointly making their feature film directorial debut and Winter starring in the 1993 science-fiction comedy Freaked. The film was never widely released, despite positive reviews from The New York Times and Entertainment Weekly. It has since become a cult favourite.
Winter did not return to directing until 1999, when he filmed the psychological thriller Fever which starred Henry Thomas in the lead role. The film was shown at film festivals worldwide, including Official Selection in the Director’s Fortnight at Cannes. The New York Daily News praised the film, calling it “a claustrophobic mind bender. Winter sustains an aura of creepiness worthy of Roman Polanski.”
After a seven year hiatus, Winter directed and acted in the live-action adaptation of the hit Cartoon Network series Ben 10, which aired on Cartoon Network in November 2007 and garnered the highest ratings in the channel’s history. He also 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.
Winter’s 2012 VH1 rock doc Downloaded earned worldwide critical acclaim at theatrical and festival screenings. Winter’s multiple award-winning 2015 documentary Deep Web had its world premiere at SXSW and a broadcast premiere in the U.S. on the Epix network alongside a global festival tour. The film went wide in September 2015, opening as the #1 documentary on iTunes.
In 2013, he featured in the thriller Grand Piano, starring Elijah Wood and John Cusack, in his first major feature film role after 20 years.
In 2016, Winter released a short documentary entitled Relatively Free about journalist Barrett Brown’s release from prison. This was followed in 2017 by another short documentary, Trump’s Lobby.
In 2018, Winter released two documentaries, The Panama Papers, about the Panama Papers, and Trust Machine: The Story of Blockchain, which premiered in Los Angeles on November 16, 2018.
In July 2015, Winter began work on a biographical documentary of the rock guitarist and composer Frank Zappa. The Zappa Family Trust publicly gave its approval to Winter’s plans for the film. Released on November 27, 2020, Zappa was the first documentary with access to his archives, and was the highest funded documentary in crowdfunding history, via Kickstarter.
Winter returned as Bill Preston in the film, Bill & Ted Face the Music, which was released on August 28, 2020; with Reeves describing the plot as, “Basically, they’re supposed to write a song to save the world and they haven’t done that.” In January 2024, Alex hinted about a possibility of a 4th film “Bill & Ted 4”.
Winter’s feature documentary The YouTube Effect, was produced in 2022 by Winter and his company, Trouper Productions, in partnership with Gale Anne Hurd and Glen Zipper. The film premiered at Tribeca in June 2022, completed a sold-out theatrical run in July 2023, and was released worldwide on digital from Drafthouse Films on August 8, 2023.
In 2024, Winter produced and co-starred in the gonzo horror-comedy Destroy All Neighbors which premiered on Shudder and in limited theaters in January 2024.
In 2025, Winter produced, directed and starred in the feature film Adulthood.