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Bradley Whitford in Billy Madison

Over the years, Bradley Whitford has played some of the best characters on television with the likes of Josh Lyman on The West Wing, Marcy/Magnus Hirschfeld on Transparent, and Commander Joseph Lawrence on The Handmaid's Tale, all of which netted the accomplished actor Primetime Emmy Awards. To some people, myself included, Whitford will always be known for his uncanny ability to play a jerk better than just about everyone. Whether it's a maniacal prick in Billy Madison or a condescending, racist, and odd asshole in Get Out, Whitford is not only great at portraying a jerk, he has range when doing so.

So, with Adam Sandler movies and Aaron Sorkin productions getting a lot of attention here recently, I've been looking back on the career of Bradley Whitford and some of the biggest pricks of his repertoire of detestable, unlikable, and downright awful characters. Here are just seven of the times he's played the perfect jerk.

Jim Downey, Bradley Whitford, and Adam Sandler in Billy Madison

Billy Madison (Eric Gordon)

You couldn't have a list of Bradley Whitford's biggest jerks without including his character from Billy Madison, and it would be impossible to start off with anyone but Eric Gordon. The executive vice president of Madison Hotels who has a history of manipulation, extortion, and unlawful possession of a loaded firearm in a public school setting is perhaps the most irremediable character Whitford has ever played, which is why it remains his most recognizable character after all these years.

From the first time we meet Eric Gordon in the opening act of the 1995 Adam Sandler classic, we know we're not going to like this guy (I mean, my brothers and I were sending gifs of Bradley Whitford while I was writing this and they were all from the opening dinner scene) and it only gets worse from there. Always in the background pushing chess pieces (and an odd cutout of Billy Madison's face with black lipstick and punched out eyes) throughout most of the movie, Eric puts it in overdrive when he blackmails Principal Max Anderson (Josh Mostel) with the August 1983 edition of Wrestling World. When that plan fails, he threatens to take Brian Madison (Darren McGavin) to court before the climatic academic decathlon.

Bradley Whitford in Get Out

Get Out (Dean Armitage)

When we first meet Bradley Whitford's Dean Armitage in Jordan Peele's 2017 instant classic Get Out, something seems a little off about the neurosurgeon who seems a little too eager to meet Chris Washington (Daniel Kaluuya). With comments about wanting to vote for Barack Obama a third time and trying his damnedest to not come off as racist in the same way that an overcompensating baby boomer is oft to do, we can't help but think about how things are going to turn out and how the good doctor will be revealed to be a jerk, and an evil one at that.

By the time we see Dean Armitage holding an auction for Chris Washington in what is later revealed to be a plan to put Jim Hudson's (Stephen Root) brain in Chris' body, we realize that yep, Bradley Whitford is once again playing a jerk, but instead of blackmailing or pulling out a gun, he has kidnapped and sold a black man so that his wealthy, elderly, and extremely white friends can take his body. And while he's not as mean-spirited as Eric Gordon here, Dean's intentions, philosophies, and actions are even more upsetting.

Bradley Whitford in Adventures in Babysitting

Adventures In Babysitting (Mike Todwell)

Before we even meet Bradley Whitford's Mike Todwell at the beginning of Adventures in Babysitting, we know he's going to be a prick. First of all, he pulls up in a red Camaro with a license plate reading "SO-COOL," and then honks his horn to let Chris Parker (Elisabeth Shue) know that he's arrived (never do that, it's very much not cool). And although his girlfriend is all dressed up in a nice dress and jewelry, Mike shows up in jeans, dirty sneakers, a leather jacket, and the worst pair of aviators you'll see in a Chris Columbus movie. Armed with a bad haircut and even worse excuse, Mike cancels the date at the fancy French restaurant in Chicago, breaking Chris' heart and setting up the plot of the movie.

Near the end of the movie when Chris and the Anderson kids are trying to find the babysitter's best friend, she encounters Mike and his new date at the same French restaurant the jerk couldn't make earlier in the evening. He gets his comeuppance in the end and is kicked into the table, ruining his dinner, but that doesn't excuse his actions, including honking to announce his arrival. I mean, who does that?

Bradley Whitford in Scent of a Woman

Scent Of A Woman (Randy Slade)

Bradley Whitford is only in Scent of a Woman for a cup of coffee as Randy Slade, the younger brother of Al Pacino's Lt. Col. Frank Slade, the blind retired Army officer, but during the tense dinner, the dickish younger brother reveals how Frank lost his eyesight in the first place, and he doesn't hold back. Between putting down his older brother's drinking problem and the drunken games he played that cost him his sight, Randy (that's such a great name, by the way) gives Frank and Charles Simms (Chris O'Donnell) some great Bradley Whitford looks that we have all come to know so well over the years.

And it's not what Randy is telling his older brother that makes his character such a jerk, it's the air of entitlement and disdain the really drives the point home. He's not telling a cautionary tale, he's putting his brother down in front of the whole family because he knows it's going to get a reaction. And soon as Frank reacts (by putting him in a chokehold), Randy immediately plays the victim. Look at his face in this clip and try not to see the cowardice of Randy take over his demeanor after acting like such a tough guy just moments earlier.

Ed Lauter and Bradley Whitford in Revenge of the Nerds II: Nerds in Paradise

Revenge Of The Nerds II: Nerds In Paradise (Roger Latimer)

If Lewis Skolnick (Robert Carradine) and the rest of the Tri-Lambs thought there was no one worse than Stan Gable (Ted McGinley) in Revenge of the Nerds, they were in for a rude awakening in the 1987 sequel, Revenge of the Nerds II: Nerds in Paradise, where they met Bradley Whitford's Roger Latimer, the head Alpha Beta at the national fraternity conference. When he wasn't giving the "nerds" the wrong directions to a party, he was busy coming up with new by-laws surrounding physical fitness standards and framing the Tri-Lambs for stealing his car. But that's not the worst.

In a final attempt to get rid of Tri-Lambs, who did nothing to him in the first place, Roger had them kidnapped and dumped on a deserted island. This alone could have resulted in the deaths of multiple people, but Roger, he don't care. Luckily for everyone not named Roger, the king jerk is voted out of the fraternity and the conference after getting decked by Lewis, who always seems to come out ahead in these movies.

John Christopher Jones and Bradley Whitford in Awakenings

Awakenings (Dr. Tyler)

Although he's not in Awakenings all that much, Bradley Whitford's portrayal of Dr. Tyler at the New York psychiatric hospital where Dr. Malcolm Sayer (Robin Williams) attempts to treat catatonic patients is pretty remarkable even if he has only a few lines and some awful body language. And it's true that Dr. Kaufman (John Heard) is the biggest jerk of the bunch in the 1990 medical drama, but Dr. Tyler's demeanor and way of dismissing everything that Sayer says should be remembered, especially when he mocks Sayer in saying "the will of the ball."

And within this minor role lies the brilliance of Bradley Whitford's ability to play a jerk better than most. It's like it's a natural tendency of the award-winning actor to act in this way. But as we see in his other performances, especially as Josh Lyman in The West Wing, Whitford is just a remarkable actor.

Richard Jenkins and Bradley Whitford in The Cabin in the Woods

The Cabin In The Woods (Steve Hadley)

And then there is the horror-comedy The Cabin in the Woods, in which Bradley Whitford plays Steve Hadley, one of the two scientists who run the simulated cabin in hopes of providing the gods with human sacrifices to avoid the destruction of the world. And though it's true that neither Hadley nor Gary Sitterson (Richard Jenkins) is a major jerk in the movie (they're just doing what needs to be done to ensure the survival of the human race), their large-scale betting pool and disdain towards other departments comes off as douchey.

But hey, throughout The Cabin in the Woods, Steve keeps talking about wanting to see a merman and is genuinely bummed when he was so close to seeing the elusive beast after all these years. Fear not, as Steve gets his wish in one of the movie's most fulfilling and heartwarming death scenes when he meets his death by the webbed hands of the sea-monster.

I will admit, it has been fun looking back on all the awfully jerky characters Bradley Whitford has played over the years, but let's not forget that he's done more than just play some of the most hated characters the past 35 years. But I can't deny the fact that he will always be Eric Gordon, either.

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