How Bradley Whitford Became One Of Our Favorite On-Screen Dickheads

Before we had the chance to observe and “know” the human side of actors via social media (or at least the version of themselves that they decided to free to the masses) we only knew them as the characters that they played on television and in movies. I assume that that was exquisite for some, but for others, constantly playing “the dickhead” had to take its toll.

Bradley Whitford, who you most likely remember from his role as Josh Lyman on The West Wing, is an actor who made his living.playing dickheads in the ’80s and ’90s. So synonymous was Whitford (who is probably a very nice guy) with dickhead roles that, according to a profile that his brother David wrote about him for Esquire back in 2001, even a homeless person recognized him as “that” guy.

One night when my brother was in New York, a homeless man sitting on the sidewalk at Eighty-eighth and Columbus said to him, “I know you. You play the *sshole in movies.” Brad gave him a buck anyway, then went straight home and called his agent. “You have to do something,” he pleaded. “People without VCRs–people without heating–are typecasting me!”

Whitford’s appeal worked, and he was eventually able to do the near-impossible and breakaway from the public’s perception of him, thanks to the high caliber material of The West Wing and his talent as an actor.

Despite that glorious pivot, we still remember when on-screen Bradley Whitford seemed like a real dick. Let’s revisit some of the highlights:

Adventures in Babysitting

In Adventures in Babysitting, Whitford plays Mike, a potential dreamboat who rejects a night out on the town with Chris (Elisabeth Shue) to supposedly care for his sick little sister before being found out as a cheating dickhead who uses and re-uses cheesy come-on lines. He also drives a Camaro with a “So Cool” vanity plate.

Revenge of the Nerds 2: Nerds in Paradise

Whitford gets a fair amount of screentime in this sequel, serving as the dim Alpha Beta leader who is hellbent on driving the nerds into the sea by any means necessary. His biggest dickhead move? Framing the Tri-Lambs for car theft after toying with their emotions.

In the end, though, Robert Carradine’s character gets the nerd revenge that the title foretold when he punches Whitford’s Roger character in the nose after he goes next level dickhead and wraps up a harsh takedown with the word “comprende.”

Billy Madison

Following Revenge of the Nerds 2, Whitford made his way to the big leagues, playing lesser “dickhead” roles in acclaimed dramas like Philadelphia, Scent of a Woman, and A Perfect World. In 1995, though, Whitford returned to his comedy roots for Billy Madison to play a scheming villain that was so cartoonishly evil and over-the-top that it almost felt like a spoof of the dickheads that Whitford had played before. Eric Gordon’s use of blackmail, gunplay, and caged rats sets him apart, though.

The West Wing

Yes, The West Wing. In The West Wing, Whitford’s character Josh Lyman can be a dick, but for the most part, he never goes above smarmy and it’s acceptable since he’s also extremely passionate and articulate as he fights for what he believes in. Basically, Josh Lyman is the dickhead of the people, but while Whitford deserves a lot of respect for toeing the line, Aaron Sorkin also deserves credit for giving Whitford a role with actual layers, allowing his edge to shine through without defining his character.

Cabin in the Woods

To me, Whitford has never played a better dickhead than the one he plays when he’s playing Hadley, a smug office drone who happens to be partially in-charge of staving off the apocalypse. Really, this is like the darkest timeline version of Josh wherein his “for the greater good” inclinations mutate and mix with an honest zest for his work to create a psychopath that is really pulling to see a Merman eviscerate a group of innocent teenagers.

In some ways, I feel like Hadley is the culmination of Whitford’s journey toward becoming a master at playing jerks and dickheads and it should be celebrated for that.

By cracking the code and mastering the dance of the on-screen dickhead, Bradley Whitford has come out on the other side seemingly able to avoid typecasting, as has been evidenced by his tonally diverse recent slate with The Trophy Wife, Transparent, and Saving Mr. Banks. Here’s hoping that continues.