Stephen Root’s Funniest Characters

Comedy Lists

Stephen Root’s IMDb profile lists over 200 credits in both films and TV shows, doing both on-camera roles and voice work for animated series. That includes everything from historical dramas to children’s fare; from prestige TV to raunchy comedies. In other words, he’s the consummate character actor, willing to throw himself into the hands of whatever project tickles his peculiar fancy. With the recent premiere of his latest film role, in the Jason Schwartzman-starring 7 Chinese Brothers, we decided to offer up our picks for Root’s best comedic performances.

1. Jimmy James in NewsRadio

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This beloved sitcom already featured one of the most perfect casts around, but it was all held together by the brilliant work that Root did as Jimmy James, the billionaire business magnate that for some reason likes to spend a lot of his time at this talk radio station he owns. Root imbued this character with all the swagger and ego of a very rich man while also holding his own against some of the finest comic actors of the time, including the late Phil Hartman and Kids In The Hall member Dave Foley. He brought out that strange energy that you see in most presidential candidates, expressing deep caring and casual disregard at the same time.

2. Milton Waddams in Office Space

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Great as he was in NewsRadio, the world will long remember Root for his performance as Milton, the mealy-mouthed, long-suffering drone at IniTech who wants nothing more but to keep his sweaty hands on the coveted red Swingline stapler. For as great as his vocal work is, Root’s physical comedy here is priceless, as he shuffles and twitches and jerks his head around like a nervous squirrel.

3. Bill Dauterive in King of the Hill

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The most pathetic of Hank Hill’s drinking buddies/neighbors, Bill is the sad sack in the wife-beater who lusts after Peggy Hill, tends to hurt himself, and always looks like he has the weight of the world resting squarely on his shoulders. Versatile voice actor that he is, Root brought out the warm heart that lay underneath the muck of this poor guy’s life so that viewers found themselves rooting for him even though his every endeavor was likely a lost cause.

4. Judge Mike Reardon in Justified

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Root’s appearances on Justified made him seem like a ringer, or the kind of injection of weird energy that the writers felt they occasionally needed to mainline into the knotted up intrigue of this crime drama. Though the character was a bit of a hardass on the bench, when he was off the clock, he oozed the Southern charm and braggadocio you’d expect from a Federal judge with a penchant for Speedos, firearms, and the love of an exotic dancer.

5. Gordon in Dodgeball: A True Underdog Story

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The producers of this half-assed comedy didn’t ask much from Root, other than to replicate his work as Milton in Office Space. But the actor still gave it his all, adding a bit of a lost lizard-like quality to his character’s physicality. Like Bill Dauterive, you wanted this sweaty simpleton to triumph, which is why his big shining moment of rage in the dodgeball tournament was so damn satisfying.

6. Radio Station Guy in O Brother, Where Art Thou?

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Root only had a few short moments in this comic road movie, but he sure left one hell of an impression as the blind, cornpone impresario of a recording studio in the rural South. It’s a performance that’s just over the top enough as he wraps his mouth around an outrageous accent and palsied mannerisms.

7. Dr. Heppa in Louie

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Another small performance for Root and one that he clearly is having fun with. As the gentlest dentist around, who helps Louis CK get through his anxiety about having his teeth checked out, Dr. Heppa helps get his patient to relax and go to sleep and…well, I won’t spoil it for you if you’ve never seen the dream sequence that follows. Rest assured that you won’t look at bananas the same way.

Robert Ham is a Portland-based freelance writer and regular contributor to Paste. You can follow him on Twitter.

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