Hilary Swank shook the cinematic world when she signed on to play the character of Brandon Teena, a pre-op transgender female-to-male in the film ‘Boys Don’t Cry.’ While it met critical acclaim it also met some disdain as the sexy starlet pulled off her role a little too convincingly, trading in her long locks for a shorter do (that arguably looks like the Bieb’s current haircut), and her femininity for a boyish look that consisted of flannels and man pants. Boys may have cried, but Swank didn’t – she nabbed the Academy Award and Golden Globe for Best Actress that year.