There’s nothing weirder than watching an actor who gets typecast as a wimp make that strange transformation into a cinematic pimp. Like seeing the president of the chess club from your freshman year of high school turn into the guy who rides a motorcycle by the end of his senior year, it gives all of us hope.
7. Val Kilmer
Source: Columbia TriStar Home Video
Val Kilmer got his first big break playing uber-nerd Chris Knight in the ‘80s classic Real Genius. The only guy who out-nerded him in this movie was Mitch (Gabriel Jarret), and it was pretty close. These two science whizzes (read: wimps) are ordered by their boss, Professor Jerry Hathaway (William Atherton), to develop a lethal laser so that Hathaway can keep his kush contract with the CIA and all the money and babes it comes with.
But Kilmer apparently didn’t want to spend the rest of his days playing the bleached version of Stephen Hawking. So, for his next film, he played the bleached version of an ‘80s douchebag, Lt. Tom Kazansky, better known to his friends and the local sexual abuse hotline as “Iceman”. He was one volleyball scene on the beach away from a lifetime of pimp roles (or gay porn, if the winds had blown a bit differently): Madmartigan in Willow, Jim Morrison in The Doors, Bruce Wayne in Batman Forever, Chris Shiherlis in Heat…the list goes on.
Kilmer is proof that just because you play a guy with a big muscle in your head doesn’t mean you can’t spend the rest of your days playing a guy with muscles everywhere else.
6. Matthew Broderick
The first movie that became a hit for Matthew Broderick was War Games, where he played David the super-hacker. David was way ahead of his time in terms of nerdiness: the man had an internet connection in 1983. I mean, I didn’t even think anyone (other than Al Gore) even knew the internet existed back then. And he had floppy drives coming out his a**! This guy was not messing around.
Then along came Ferris Bueller’s Day Off in 1986. Overnight, Broderick became the symbol for teen rebelliousness and unfettered cool. From here on out, Broderick would be remembered for his turn as the teenage bad boy, no matter how many unmemorable films he did: Project X, Torch Song Trilogy, Family Business, Glory. He could never top the pimpness of Ferris Bueller, but managed to go down in history for one of the funniest teen comedies ever. That’s an accomplishment in itself.
5. River Phoenix
Source: Paramount Pictures
Remember that awesome kid movie from 1985 with River Phoenix and Ethan Hawke? Well, if you do, then you’ll remember that Phoenix actually played the lead dork/nerd/wimp, and he played it with gusto. He creates the force field bubble that he and his friends turn into a space ship and use to leave Earth. That was how the world first came to really know River Phoenix.
And then he goes and becomes young Indiana Jones in Indiana Jones and the Last Crusade four years later. The computer genius turned into an archaeologist/badass in the blink of an eye, and he never looked back. Okay, so maybe he looked back a little in 1992’s Sneakers, but pretty much he remained for the ‘90s -- even after his death -- what James Dean was for the 20th century.
4. Patrick Dempsey
Source: Buena Vista Home Video
Most people probably never saw that stupid little ‘80s movie called Can’t Buy Me Love. If you did, you might recall the little high school dork it starred. Yeah, that was Patrick Dempsey, pre-Gray’s Anatomy. Pre-McDreamy. There was nothing dreamy about him when he played Ronald Miller, the nerd so desperate to hang with the cool kids that he paid the most popular cheerleader in school to be his fake girlfriend. There were few signs that he was going to go from playing high school dorks to Hollywood docs, but such has been his career.
Dempsey didn’t do anything too drastic to emerge from the chrysalis of his wimpiness (besides get a nose job, which is de rigueur in Hollywood) other than simply let age do its magical thing. Sometimes a good layer of stubble and a few crow’s feet are just what the doctor ordered (partial pun intended), and he was wise enough to see that Botox was his worst enemy.
If we can learn anything from Dempsey’s transformation it’s that sometimes all you have to do to go from a wimp to a pimp is get older: time may hurt women but it’s a man’s best friend. That, and wearing a stethoscope around your neck at opportune moments. Calling yourself doctor automatically increases your pimpness times ten.
3. Jeff Goldblum
Source: 20th Century Fox
Jeff Goldblum has spent pretty much his entire career walking the really, really wide line between wimp and pimp. In fact, in at least a couple of movies he’s played both at the same time. When he started out, he was the obvious choice for wimpy little (and by little, I mean tall as s***) wuss roles: the first role listed on his IMDb page is Freak #1 from Death Wish and from there it doesn’t get much better. He plays gangly dork Michael Gold in the masterfully lame film The Big Chill, Buck Wolf in Faerie Tale Theatre, and Cogswell in The Ray Bradbury Theater.
And then, kapow, he’s Seth Brundle in David Cronenberg’s remake of The Fly. The Telepod that Brundle invents does two things: it fuses his genes with those of a fly’s, thus turning him into an extremely powerful mutant, and it turns a formerly nerdy Jeff Goldblum into a badass player who doesn’t take s*** from nobody.
Just to make sure we didn’t think this was an anomaly, he goes on to do basically the same thing two more times. He plays the mathematical nerd Ian Malcolm in Jurassic Park, but comes back in The Lost World: Jurassic Park as the same mathematician with brawn. And in Independence Day he plays David Levinson. He starts the movie out as an obnoxious, know-it-all little turd, but ends it as one of Earth’s first UFO fighter pilots, chomping down on a cigar after saving the planet from alien infestation. Bad. Ass.
Sometimes wimps make the best pimps is the lesson from Jeff Goldblum’s career.
2. Michael Keaton
Source: 20th Century Fox
If anyone’s climb from wimpiness to pimpness was long and arduous, it was Michael Keaton’s. Let’s not make any bones about it: the dude started out working in the art department of “Mister Roger’s Neighborhood.” He was a puppet jockey, for god’s sake! And when he did finally get his acting career going he wasn’t exactly getting cast as tough guys or ladies men. He played Jack in Mr. Mom in ’83, Beetlejuice in the movie of the same name in ’88, Billy Caufield, a mentally unstable man in a mullet in ‘89’s The Dream Team, and then – in the same year – he somehow got cast as Bruce Wayne in Tim Burton’s Batman. He went from nutjob with hair problems to Batman! If there was an award for jumping from a career of character roles to badass of the century roles in one movie, Keaton would get it.
And the funny thing about Keaton is that he wasn’t afraid of getting pigeonholed as a character actor. After the phenomenally successful Batman and Batman Returns, he turned right around and played the homeless fool Dogberry in ‘93’s Much Ado About Nothing. One second he’s taking down the Joker with his fists, and the next he is the joker and he’s busting out in iambic pentameter.
It takes an actor with a lot of range to spend his time jumping between wimps, crazies, and pimps, and nobody’s done it better than Keaton.
1. Anthony Michael Hall
Source: Universal Pictures
Nobody deserves more credit for turning a career of wimpiness on its head more than Anthony Michael Hall. He was and is to this day the prince of the high school movie nerds, and it was looking like he wasn’t ever going to escape his fate. Between Sixteen Candles, The Breakfast Club, and Weird Science, he and John Hughes wrote the rules of high school geekdom and it seemed as if Hall was going to have to start playing dorks in college movies next.
But he didn’t. Instead he played the cruel, Winona Ryder-dating, ultra-violent Jim in Edward Scissorhands in 1990. The pencil-necked, floppy haired doofus -- a walking target for bullies -- had himself become the bully. Maybe Anthony Michael Hall didn’t make the most honorable transformation into post-nerdhood, but dang if he didn’t deserve some payback after all the crap he took for his dorky time in the trenches.
Of course, many people will then point to 1999, when he played Bill Gates in Pirates of Silicon Valley. In some ways this was a return to his roots, and in others it was a kind of victory lap: the day had come when Hall could finally play wimp or pimp depending on his fancy. Fancy that, a pimp who’s not too cool to play the wimp.