She also managed to share the screen with Tom Cruise in Cocktail.
After playing in Pretty in Pink, her career really started to kick off with bigger movie roles.
Here she is making out with in Bound: Of course, she was also known for her role alongside the sexy in the infamous movie Showgirls, which was heavily criticized when it was released but has since been accepted as a cult classic.
Gershon had a ton of nude scenes in Showgirls and several sensual lesbian scenes in Bound.
Her career really took a strange turn as the lesbian ex-con in Bound.