The first thing my very straight brother told me when he first saw Eddie Redmayne as a girl was, "damn it, he's hot." Yeh. The Danish Girl was a turning point in Redmayne's acting career. I mean, the guy did get nominated for another Oscar after having won an Oscar the year before. Playing a transgender woman, was a good move for Redmayne and well, he looks pretty good — alright, amazing — as a woman.
You know, Angelina Jolie can pretty much do anything. I mean, this woman is a mother of six, she's an actress and she's a philanthropist. She's also written and directed movies, so she's pretty busy. But this picture proves she can also pull off looking like an average looking guy. One with perfect full lips but still, a guy. This is her playing a man in the movie Salt.
The first time I saw Cillian Murphy was in Batman when he played the crystal-clear-eyed scarecrow. Those piercing eyes are difficult to forget. But Murphy has done more than play the scarecrow. In 2005, he took a role in the movie Breakfast On Pluto looking like this. Much like Redmayne, Murphy sure looks good as a woman.
Glenn Close disguised herself as a man in the movie Albert Nobbs. Based in the 19th century, Close played a woman who needed to work to survive and the only way she could do that was by disguising herself as a man. And well, she pulled it off.
Boy's Don't Cry brought Hilary Swank fame and an Oscar for her role. In the movie, Swank portrays a transgender boy. It's a brilliant and emotional movie that shows the struggles a transgender person can go through.
I guess if you're a hot man, you really can pull off looking like an even hotter woman. This is what Gael Garcia Bernal has proven, much like Redmayne and Murphy. In Bad Education, this actor transformed himself into a woman and really, you wouldn't notice he's a guy if someone didn't point it out.
This theory doesn't translate for Johnny Depp. He looks like quite a mess as a woman, doesn't he? Depp played a woman in Before Night Falls and well, despite looking like this, his fans still stuck. It's hard not to.
John Travolta has been showcasing his dance moves ever since Saturday Night Fever. We get it, you can dance. But even so, this guy wanted us to know he can work the dance floor even while dressed as a curvy woman. And that's exactly what he did in the movie Hairspray.
Playing Bob Dylan is not a role to take lightly. People will tell you if they think your Bob Dylan impression sucks. I mean, it's not like people hold back online. So when Cate Blanchett played Bob Dylan in the movie, I'm Not There, it was a huge risk. Did it pay off? Well, that's up to you to decide.
It may not be his most famous role but it still showed Patrick Swayze's skills as a woman. Never has a man looked better in black eyeliner, am I right? It was in To Wong Foo Thanks For Everything, Julie Newmar, a 1995 comedy, that Swayze donned a dress.
There are a lot of Adam Sandler movies out there. Some would say there are way too many while others will tell you there aren't enough. Well, in one of these movies, Sandler got to wear a dress and play his own twin sister. The result wasJack and Jill.
Elle Fanning's acting career is already way better than some actors who have been in the game for a while. In 3 Generations, Fanning had the opportunity to show off her acting skills once again by playing a transgender boy. That's the prettiest boy I've ever seen.
Much like the rest of the actors on this list, switching genders worked very well for Dustin Hoffman. In 1982, Hoffman, playing a struggling actor, turned himself into Tootsie. A classic movie, the role even earned the actor an Oscar nomination.
It's not a classic. It's not the funniest. But, Shawn and Marlon Wayans did have the biggest gender transformation of them all when they turned themselves into blonde haired women for the movie White Chicks.
One of the most famous gender switch roles of the '90s is this one of the late Robin Williams playing Mrs. Doubtfire. Williams made nannies loveable. Of course, having to catch Mrs. Doubtfire peeing while standing up may have been a bit much for some of us.