Typecasting is death in Hollywood. If you keep doing the same kinds of roles over and over A) you’ll go insane and B) people will get sick of your shit. But the sad paradox of Hollywood is that once you’ve established yourself as one kind of actor, you’re basically stuck that way because that’s all people will send you scripts for, turning the whole thing into a spiral of bullshit.

It’s extremely difficult to break out of, and it’s ended numerous careers. (Some for the better.) Some actors get fed up with it, and then you get the roles where those actors try to break out of their type (often unsuccessfully) and as time goes by they end up looking like movies from some creepy alternate dimension or something.

But what’s also weird is going back through an actor’s early filmography and finding insane gems where they’re going totally against their later-established type. For some more famous examples, just look at Keanu Reeves in the Bill & Ted movies or Sean Penn in Fast Times at Ridgemont High. Neither of those guys would even put their cigarette out on those scripts now, and that’s what makes seeing them in those roles hilarious.

So now, in a far from comprehensive list, we’re going to look at some of the weirdest roles that actors have done outside of their typical repertoire.

Bruce Willis in Death Becomes Her

You may already know that pre-Die Hard Bruce Willis was a comedic television actor on a series called Moonlighting. Post-Die Hard, he was Bruce Fuckin’ Willis, action star and all-around genuine American badass. Later, thanks to Pulp Fiction, he became Bruce Willis, well-rounded dramatic actor and still occasional action/comedy star. But tucked in-between the first two Die Hard movies was an earlier attempt to break out of his John McClane-induced Hell, a black comedy called Death Becomes Her.

Again, comedy roles were nothing new for Bruce, but what’s weird about this one is the fact that his character is a massive, massive dweeb. You want to reach through the screen and give his nebbish plastic surgeon character a wedgie the minute you see him. At least when he played a shrink in The Sixth Sense, you still got the feeling he could kick an ass or two if it came down to it.

Seth Rogen in Donnie Darko

When you think of Seth Rogen, you think of the doofish guy who sold you weed in college, because Seth Rogen probably really did sell you weed in college. (This is true even if you’ve never smoked weed or been to college in your life.) He’s the best buddy character in like, 90% of comedies released in the last five years. He even made The Green Hornet into a bromance, for God’s sake.

But before all of that, he played a fairly minor role as a total jerk-ass bully in Donnie Darko. It’s such a small part that it probably wouldn’t  even stand out, except that he’s the guy who ends up uttering the (in)famous line “I like your boobs,” to a girl he’s taunting. Really, Seth? Now that is some smooth talking. Get you some, big fella.

Vince Vaughn in Psycho

Vince Vaughn is a man who wears many hats: Idiot man-child in Dodgeball, guy who used to slum around in Jon Favreau movies before Favreau started doing stuff like Iron Man, guy who got to schtup Jennifer Aniston in real life, guy who’s only done like five movies since he stopped schtupping Jennifer Aniston, and so on.

But in Gus Van Sant’s ill-advised Psycho remake, Vince Vaughn got to play none other than Norman Bates himself. And the weirdest part? He’s actually really good at it. Like, holy shit, that guy is terrifying. Just seeing how weird Vaughn is in the role is pretty much the only thing about that remake that makes it kinda worth watching. Unless you like seeing otherwise talented actors trying to channel forty-year-old performances, I mean.

Betty White in Lake Placid

Betty White has seen a kind of resurgence of late, thanks to weird, nostalgic people on the internet. Before social media campaigns turned her into an odd, charming old woman, she was… an odd, charming old woman. Okay, obviously nothing’s changed. Betty White‘s pretty much always played the kooky elderly woman role, something she seems to do in real life as well. When we watch Betty White, it’s like she’s not even playing a role. That’s just her on screen, being herself.

She’s kinda like your grandma, except famous and she didn’t lock you in cupboards when you misbehaved as a kid. That’s why it’s kinda odd to see her in a movie like Lake Placid, playing a woman who claims to have murdered her husband, feeds and cares for a gigantic crocodile, calls people things like “fuck-meat”, and tells a police officer to suck her dick. That’s more like the grandma most of us know. (It’s just a joke, grandma. Don’t lock me in the cupboard.)

Michael Madsen in Free Willy

Approximately 99% of people only remember the following about Free Willy: Michael Jackson. Whale. Cover art. That’s it. That’s why it may very well blow your mind to discover that Michael Madsen is totally the kid’s dad in that movie (and then it will be further blown when I tell you that that kid is now 31 years old). And he’s not an ex-cop dad who beats his kids, or a crazy dad who sits around with a shotgun. No, he’s totally a supporting, loving foster dad. This is the same Michael Madsen who played an ear-cutting jewel thief in Reservoir Dogs and Bill’s loser brother Budd in Kill Bill.

Sadly, the only decent footage on YouTube is a 3 second scene where he punches the bad guy (played by Michael Ironside) toward the end of the film. Just watch it and pretend that it cuts away before he ties the guy up and drops a car battery on his junk for an hour.

Ronald Reagan in The Killers

Good old Uncle Ronnie’s become a bit of a legend these days. The current crop of American conservatives love to reference him and his policies to win points with the Baby Boomer generation. Naturally, no one’s forgotten that President Reagan was once a popular film star, although most folks will probably tell you that he spent a lot of time doing Westerns and kissing monkeys, nothing real crazy.

However, in 1964’s The Killers, Ronald Reagan did something he had never done before or since: he totally played a bad guy. (Keep it down, grouchy, politically-minded people. We’re all just here to talk movies.) And not just any bad guy, either– he played a ruthless, bad ass mob boss, the kind of guy who was apparently okay with giving a dame what-for when she got too mouthy or whatever. Poor examples of gender relations aside, Reagan actually did a fairly impressive job. If that whole “politics” thing hadn’t worked out for him, he could have been Robert DeNiro before there even was a Robert DeNiro.

Sir Alec Guinness in Murder by Death

Sir Alec Guinness (The “sir” is mandatory) is known for a single role more so than anyone else on this list: Jedi Master Obi-Wan Kenobi. A father figure to millions of lonesome, sweaty nerds, Obi-Wan is the embodiment of calm, peaceful wisdom. He is Luke Skywalker’s and, by proxy the audience’s, first real glimpse at the vast universe of the Star Wars saga.

But what a lot of people outside of England don’t realize is that Sir Alec was an accomplished actor for many decades before being cast as Obi-Wan. And, in perhaps one of his oddest roles, he played a blind butler in Murder by Death, a slapstick comedy written by Neil Simon. Most of his laughs in the film come from his interactions with the deaf-mute maid, as seen in the clip above. It’s kind of disconcerting to see him unable to use Force Sight to find his way around.


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