10 Straight Actors Who Played Gay Roles To Perfection

6. Sean Penn: Milk

It’s true that over the years, Sean Penn has gotten a very bad reputation. From his ego to clashing with reporters to reports of being difficult on set, the man has a poor aura of being hard to work with. But when he is on, he can be one of the most electric and amazing actors alive. Penn proved that in this 2008 drama, Milk, where he took on the role of Harvey Milk, the first openly gay man elected to a government position in San Francisco. Penn throws himself into the role, making himself sound like the real Milk and doing a great job with how the man wasn’t hiding who he was (a major move in the 1970s).

More than once, Milk is told he has to “tone it down” if he wants to make it, but refuses to. Although ironically the local gay community feels he’s “straightening up” too much for their liking. Milk just wants to be himself and serve his community, but he is judged on his sexuality a lot and Penn shows the pride and strength that drove him on. His story ended tragically as he, along with the mayor of the city, were shot and killed by a troubled co-worker in City Hall. Penn won an Oscar for the role and showed that, prickly reputation aside, he is an actor believable in any part.

7. Charlize Theron: Monster

Charlize Theron had always been known as a very hot and sexy woman. She showed that in a bevy of roles, many with her stripping down a lot. Thus, while she had talent, most still dismissed her as just getting jobs more for her looks. Which was why critics and audiences were utterly stunned when Theron turned in what Roger Ebert hailed as “one of the greatest performances in movie history.” As real-life serial killer Aileen Wuornos, Theron is buried in a makeup job that makes her almost unrecognizable. She shows the pain of this prostitute, who claims she’s not gay but soon falling for a lady she meets in a bar (Christina Ricci). But after suffering abuse from her “clients”, Aileen is on a murder spree that makes her infamous. Despite that, you feel for her, the obvious love for Ricci, the one thing that grounds her and makes her almost relatable. Theron won just about every Best Actress award there was for the part, including an Oscar, and while it’s hard to cheer this woman on, her struggles were totally believable.

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