Entertainment Why Stephen Root Is The Weirdest Actor In Hollywood  

Donn Saylor
201 votes 81 voters 3.1k views 12 items

List Rules Vote up the facts, stories, career choices, and other ~quirks~ that you feel truly make Stephen Root one of Hollywood's weirdest actors.

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 with a remarkably productive resume.

A one-hit wonder Stephen Root is not. It's quite possible that you've seen Root in some of your favorite films and completely overlooked him. The guy transforms both physically and emotionally so as to render himself unrecognizable from role to role. He also has a knack for choosing unusual characters.

Read on to learn all about Stephen Root, his career, and his wonderful weirdness.

1 22 VOTES

He Portrays Jimmy James On NewsRadio

He Portrays Jimmy James On New... is listed (or ranked) 1 on the list Why Stephen Root Is The Weirdest Actor In Hollywood
Photo:  Sony Pictures Television

One of his first highly visible television roles, Jimmy James from NewsRadio is another exemplary Stephen Root character. James is the domineering oddball station owner on the show and Root cherished the character.

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."

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2 23 VOTES

Root Plays A Gay Vampire On True Blood

Root Plays A Gay Vampire On Tr... is listed (or ranked) 2 on the list Why Stephen Root Is The Weirdest Actor In Hollywood
Photo:  HBO

In a career that's included a lot of out-there roles and unusual approaches to character idiosyncrasies, Root's performance as gay vampire Eddie Fournier on True Blood is a standout. What could have easily been an over-the-top caricature was instead a thoughtful and nuanced study of a lonely but endearing middle-aged man. Sure, Eddie was a vampire but he was sweet and gentle. Root has acknowledged that the role was "a leap into the unknown" for him but the leap proved well-timed and well worth it.

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He Did Theatre For 15 Years Before Working In Film And Television

He Did Theatre For 15 Years Be... is listed (or ranked) 3 on the list Why Stephen Root Is The Weirdest Actor In Hollywood
Photo: Matim2000/Twitter

Root didn't start out with a high-profile Hollywood debut. Like many actors, he first honed his craft on stage and he stayed there for 15 years. He has often talked about the excellent foundation that his theatrical career provided him. He actually stated that his Shakespeare training helped him play a Klingon in an episode of Star Trek. "I could actually use my Shakespeare training to talk over the dentures," Root said.

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4 29 VOTES

Root Plays Milton In Office Space

Root Plays Milton In Office Sp... is listed (or ranked) 4 on the list Why Stephen Root Is The Weirdest Actor In Hollywood
Photo:  Office Space/20th Century Fox

Milton Waddams, the lowly and bespectacled office drone who's 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 theatres and the actor is constantly gifted with staplers. 

As outlandish as Milton may seem, the character's actually rooted in a truth that Root tapped into. "A friend of mine emailed me and he works with some real corporate assh*les, 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?'"

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