Film
Gershon's break came with a bit part in Pretty in Pink (1986), which led to more substantial roles in Sweet Revenge with Nancy Allen, Cocktail with Tom Cruise and Elisabeth Shue, and John Sayles' urban drama City of Hope (1991). Also in 1991, she appeared in the action film Out for Justice opposite Steven Seagal, where she played Patti Madano, sister of the film's villain, Richie Madano (William Forsythe). Gershon also worked in television, with a recurring role on Melrose Place playing a prostitute working for a Heidi Fleiss-esque Hollywood madam.
In 1996, she played Corky, an ex-con who gets mixed up in an affair with Violet (played by Jennifer Tilly) in the crime film Bound. In 1997, she co-starred with John Travolta and Nicolas Cage in Face/Off.
Gershon is regarded as a gay icon for her roles in films such as Bound (in which she played a butch lesbian), Prey for Rock & Roll, and Showgirls (in which she played a bisexual showgirl, and which is regarded as a camp classic). She was ranked #51 on the Maxim Hot 100 Women of 2004.
In 2011, Gershon appeared alongside Matthew McConaughey in Killer Joe, a dark comedy/thriller featuring director William Friedkin.
In 2017, Gershon starred in Bad Kids of Crestview Academy directed by Ben Browder, Lost Cat Corona directed by Anthony Tarsitano, the romantic comedy-drama Permission opposite Dan Stevens and Rebecca Hall directed by Brian Crano, Gershon co-starred alongside Nicolas Cage in the thriller Inconceivable, thriller film directed by Jonathan Baker, That same year, she starred in 9/11 directed by Martin Guigui revolving around the September 11 attacks opposite Whoopi Goldberg, Luis Guzmán and Charlie Sheen. The film was panned by critics and faced controversy for Sheen's history with the 911 Truth movement, a conspiracy theory. Gershon stated she was unaware of Sheen's comments during production of the film and would have spoken with Sheen and Guigui before agreeing to star.
In 2018, Gershon starred in the adventure drama American Dresser directed by Carmine Cangialosi, which was critically panned. Gershon then starred in the drama film After Everything directed by Hannah Marks and Joey Power, opposite Maika Monroe and Jeremy Allen White. The film had its world premiere at South by Southwest in March 2018, and was released in October 2018, to critical acclaim. She also had a small role in comedy Blockers directed by Kay Cannon, which was released on April 6, 2018, to critical and commercial success.
In 2020, Gershon starred in the sports film Cagefighter: Worlds Collide directed by Jesse Quinones. Gershon next starred in Rifkin's Festival directed by Woody Allen. Following backlash for starring in the film, Gershon defended her decision to star in the film stating: "I don't believe that to be true. You should really do all of the research and read all of the articles before believing that. It's really important to make up your own mind and not go by what the masses claim. I've done extensive research and I can say with very clear conscience that I'm so happy to be working with him. This man is not a sexual predator." Gershon also called working on the film "a dream come true". In 2021 Gershon starred in With/In an anthology film set during the COVID-19 pandemic directing from a screenplay she wrote.
