Many of us first became aware of Stephen Root's acting prowess in the 1999 classic Office Space, where his character Milton Waddams stole the show and secured a prominent place in pop culture history. Root had already been acting for over a decade before that breakout hit, though. In the years since Office Space, he has become one of the most prolific and chameleonic character actors around, boasting a remarkably productive resume. He seems to show up everywhere and in everything (over 800 episodes of television and 100 films, as of 2020).
"I knew I wanted to be a working actor," Root told The A.V. Club. "And as the years have gone on, I just naturally evolved into [a character actor]. Because, y'know, I'm not a leading guy. Never was. It was just a natural progression to keep doing this. I mean, Betty White's, what, 90? And she's still working!"
A one-hit wonder Stephen Root is not. It's quite possible you've completely overlooked Root in some of your favorite films and TV shows. If you haven't, then you know he is one of the greatest character actors of the past 30 years; the guy transforms both physically and emotionally, rendering himself unrecognizable from role to role. He also has a knack for choosing unusual characters. In pretty much every case, he brings a wonderful amount of creativity and weirdness to each role, subtly enhancing everything he appears in - whether you recognize him or not.
Milton Waddams, the lowly and bespectacled office drone relegated to a basement desk while harboring a deep appreciation for his red stapler, is cinematic gold. Stephen Root's portrayal of him is perfect. Devoted fans that call themselves "Milton people" still wait for Root outside of theaters and the actor is constantly gifted with staplers.
As outlandish as Milton may seem, the character was actually rooted in a certain truth Root was able to tap into. "A friend of mine emailed me and he works with some real corporate a**holes, and said literally one of his bosses moved another guy into a storage room," Root explained. "He asked, 'Please, would you mind sending him a stapler?'"
With his Coke bottle glasses, greasy hair, and protruding paunch, Milton isn't exactly a head-turner. Root's transformation into such an unappealing (yet lovable) character is a testament to his flexibility. He, unlike more vain actors, doesn't mind playing either the off-putting or the mundane.
Bill Dauterive on King of the Hill is another memorable character brought to life largely by Root's unique skill set. In a sense, creating a distinctive animated character is much tougher than doing live action; an actor must rely solely on his or her voice to make an impression. Root pulls it off brilliantly, making Bill into one of the most memorable TV characters of the era.
A lovable loser and eternal sad sack, Bill allows viewers to laugh at him without feeling too guilty. Root even had an elaborate and slightly morbid backstory for Bill, including how the character would one day perish:
Whenever Bill would finally go, it would be in a very small bathroom, behind the door that you couldn't get open to get him. He would die back there. You just couldn't get to him.
Root also voiced Buck Strickland on King of the Hill as well as a plethora of other characters across animated television and film (including Bubbles in Finding Nemo).
One of his first highly visible television roles, Jimmy James from NewsRadio is an exemplary Stephen Root character that shows off everything from Root's comic chops to his idiosyncrasies to his authoritative side. James is the domineering oddball station owner on the show, a character Root still cherishes to this day.
The actor also recognized how special NewsRadio was. "I think it's still underrated," he told TV Guide many years later. "I think it was one of the best shows on TV in terms of the cast and the writing. We were under the radar... [but we] knew it was special."
Root is a character actor of the highest order - a true artist with abilities that allow him to play a remarkably diverse assortment of roles. One of his most entertaining characters is Gordon Pibb from DodgeBall: A True Underdog Story. Root shows up in a manner that's essentially a replication of his work in Office Space, only spiced up with a physicality previously attributed only to reptiles.
Root can play both confident and corny so well that we both root for, and despise, many of his characters; Gordon Pibb achieves the former, especially when he triumphantly evolves in the film's climatic tournament.