It's no surprise that we're seeing so many fantastic character actors on this list; not every actor is capable of portraying someone of a different sexual orientation convincingly, but great performances come naturally to Oscar winner Hilary Swank. Swank has actually picked up 'Best Actress' twice at the Academy Awards, and the first of them was for 1999's 'Boys Don't Cry.'
In the film, she plays Brandon Teena, a trans man. Swank is utterly androgynous in her performance, and as a comparative unknown at the time the audience wouldn't have known for sure whether they were seeing reality or fiction. Brandon Teena really existed, and the film is his harrowing story. It's gritty stuff, and difficult to watch at times, but Swank is simply phenomenal in the part. In reality, at the time of filming she was married to Chad Lowe.