They’re some of the most lovable actors in Hollywood. They always play the hero, the comedian or the nice guy. But once they’re typecast, they desperately find ways to expand their horizons, and often opt to play the villain, with varying degrees of success.

Here are five nice guy actors who tried to go evil.

Ryan Reynolds – From Van Wilder to Amityville

In my estimation, Ryan Reynolds is one of the most likable actors working in Hollywood today, and unlike some others on this list, I think he’s pretty damn awful at playing the villain. As the smooth, witty charmer, he has no equal, but when he tried to go all family-murdering psychopath in The Amityville Horror, it just flat out didn’t work. He needs more than a beard to make him evil, and frankly the audience couldn’t help but be on his side throughout most of the film. His family was pretty damn annoying.

Robin Williams – From Patch Adams to Sy Parrish

I believe that Robin Williams does drama much better than he does comedy, and one of my favorite performances from him is in the often overlooked horror/drama, One Hour Photo. Williams plays a deeply disturbed photo clerk with an unusually strong attachment to a family, and by the end he snaps and dons a big ‘ol hunting knife to teach someone a lesson about family values. To be fair, this isn’t William’s only foray into the disturbing and you should watch Insomnia and Death to Smoochy for other examples.

Jim Carrey – From Ace Ventura to 23

But while Williams is more adept at drama than his natural comedy, Carrey is the opposite, and should run away from horror like it’s trying to stab him with a butcher knife. His turn as a crazy conspiracy theorist obssessed with the number 23 made for one of th e absolute worst horror movies I’ve ever seen. A saxophone and tribal tattoos? Yeah, just terrifying man, really. You’ve totally got the hang of this genre.

Harrison Ford – From Indy to What Lies Beneath

He’s played at least four of America’s greatest heroes (Indiana Jones, Han Solo, Jack Ryan and President “Get off my plane”), so to see Harrison Ford as a murderous husband was a bit of a shock. What Lies Beneath wasn’t the worst scary movie ever, but it’s far short of a classic, and aside from a particularly memorable bathtub scene, really has nothing worthwhile in it.

Elijah Wood – From Frodo to Kevin

Wood’s mute performance in Sin City as cannibalistic, acrobatic psychopath Kevin was one of my favorite things about the film. Taking one of the most innocent looking actors in Hollywood and turning him into an unrepentant killer was a genius move, and I’d really like to see Wood branch out into more roles like that. Except once he opens his mouth, all that badassery goes away.