Stephen Root opens up about the high-stakes career gamble

Stephen Root ditches the theatre to make his career in Hollywood. The decision was made more out of responsibility than out of passion.

During his recent interview with Rolling Stone, “You can’t sustain a kid on theater money, so we moved”. Long before becoming a fixture on film and television screens, Root was immersed in theater. After attending the University of Florida, he left before graduating and joined a traveling Shakespeare troupe, performing across the country and taking on whatever roles were needed.

The demanding schedule required actors to take on multiple parts, helping Root develop the versatility that would later define his career. His stage work eventually led to a steady presence on Broadway, including a role in a 1987 revival of Arthur Miller’s All My Sons.

By the late 1980s, however, Root’s personal life had changed. He and his first wife, Laura Joan Hase, whom he married in 1984, were raising their son, Cody, and the demands of supporting a family made the financial uncertainty of theater increasingly difficult to justify.

As he recalled the high-stakes move to Hollywood, Root told Rolling Stone that to “book immediately,” they “rented a house in Woodland Hills”.

The gamble paid off, though not without setbacks. After landing small parts in films including Ghost and Crocodile Dundee II, Root appeared to catch a major break when he secured a role in Arnold Schwarzenegger’s Kindergarten Cop. The film became a box-office hit, but his scenes never made it into the final cut, which reinforced just how difficult life could be for a working character actor trying to gain a foothold in Hollywood.

“I’m not a known commodity, not a name. So anything you get that has meat in it, in terms of real work in a movie, was rare,” he explained to Rolling Stone. “You’re doing your character-actor stuff, and if you don’t get a chance to be seen as the old character actors did in ’30s and ’40s movies, then you kind of disappear.”

Nevertheless, a major turning point in Root’s career arrived in 1995 when he landed the role of eccentric billionaire boss Jimmy James on NewsRadio. A few years later, he joined the cast of the cult-classic comedy film Office Space.

From there, he began booking steady work, leading to roles like Bob Mayer in The West Wing, Monroe Fuches in HBO’s Barry, which earned Root a 2019 Emmy nomination for Outstanding Supporting Actor in a Comedy Series, and his most recent turn as Wyck in Apple TV’s Widow’s Bay.

From the soft-spoken Milton Waddams in Office Space to the perpetually heartbroken Bill Dauterive on King of the Hill, Stephen Root has spent decades portraying outsiders, underdogs, and complicated men.