11. Hilary Swank
Way before it was cool to be gay on film, Hilary Swank broke some ground with Boy Don’t Cry in 1998. She serviced Chloe Sevigny in a very passionate kiss below the Mason-Dixon line. The love scene was about the only high point in an otherwise depressing bio-epic. Swank won an Oscar for the transgender role. She also won for Million Dollar Baby, as a boxer who gets paralyzed in the ring. She played another butt kicker in Karate Kid 4, one of her first major films. Her big break was a role in the latter seasons of the iconic 1990’s television show, Beverly Hills 90210.
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