Fenn landed her first starring role, as an engaged heiress to an old Southern family who falls for carnival worker Richard Tyson, in Zalman King's erotic drama film Two Moon Junction, after which she wanted to hide for a year: [7] "I was so embarrassed about how it turned out that I went into a cocoon for a year afterwards." [8] Two Moon Junction was meant to be Fenn's big break, but the film turned into another sexploitation film. In 1994, Fenn married guitarist-songwriter Toulouse Holliday, [53] whom she met on the set of Three of Hearts.

In 1996, the Daily Mirror chose her as one of the "World's 100 Most Beautiful Women", and Femme Fatales chose her as one of the "50 sexiest sci-fi actresses". [61] I fought to keep the integrity of the story because the producer was bringing in a writer that was making it very soapy. They wanted many scenes of her when she was very overweight. I said, 'I'm not doing that. I'll do one. That's not this woman's life.' For me it was just: I didn't want to make an impression. I just tried to play the truth of the woman. [15] Mid 1990s and guest appearances (1996–1998) [ edit ] After finishing the Russia-set action film Treasure Raiders with David Carradine, Fenn starred in the Canadian psychological thriller Presumed Dead, alongside Duncan Regehr, as a detective working on a missing-person case who has to outwit a crime novelist. She began to alternate TV movies and independent films. In 1996, she joined the ensemble cast in the romantic comedy Lovelife as a waitress who attempts to become a writer and has to rebuild her life. Fenn also appeared in the 1997 romantic comedy Just Write, along with Jeremy Piven, as the dream actress of a Hollywood tour bus driver, who mistakes him for a famous screenwriter. Both films have been well-received on the festival circuit. Sherilyn Fenn: Fenn de Siecle". Movieline. January 7, 1993. Archived from the original on December 28, 2010 . Retrieved October 8, 2010.

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In 1999, she reteamed with Chris Penn and Adrian Pasdar for Pasdar's art-house directorial debut, the neo-noir Cement, a contemporary retelling of Othello in which she played a tempting but imprudent wife of jealous corrupt cop Penn. "I play a character who's selfish and sloppy with her sexual energy. I saw the film and I was really happy with it. It's got a lot of soul." [28] The film, which won Best Picture awards on the festival circuit, was written by Farscape 's screenwriter, Justin Monjo and also starred Jeffrey Wright and Henry Czerny. She also reteamed with actor/director Bruce Davison for his 2001 family comedy, Showtime's Off Season alongside Rory Culkin, Hume Cronyn, and Adam Arkin.

Sherilyn Fenn, quoted in "Elizabeth Taylor television film to be shown over her objections." Reading Eagle TV Times (US). May 21, 1995. p. 31.

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Lionsgate Publicity: February 2009". Lionsgateinfo.com. Archived from the original on July 13, 2011 . Retrieved April 25, 2010. Audrey's been great for me. She has brought out a side of me that's more mischievous and fun that I had suppressed, trying to be an adult. She has made it OK to use the power one has as a woman to be manipulative at times, to be precocious. She goes after what she wants vehemently and she takes it. I think that's really admirable. I love that about her. [10] Fenn dated pop singer Prince for a short time during 1985 and then Johnny Depp the same year; their relationship lasted several years.

Sherilyn Fenn, quoted in "Babes in the Woods: Sharing Pie and Secrets With the Mystery Girls of Twin Peaks" by Bill Zehme. Rolling Stone. Issue 588. October 4, 1990. pp. 68–71, 170. Lester Perky, quoted in "Legendary Portrayal" by David Walstad. The Philadelphia Inquirer TV Week (US). May 21, 1995. pp. 4–5. Lucid, sculptural, unpresumptuous Sherilyn Fenn made her movie debut at 17. In Yugoslavia. Playing a shy rich girl, a sort of Yugoslavian coed Lord of the Flies. “I remember blowing my first scene. I said, ‘Cut!’ I didn’t know the director was supposed to say that.”

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In 2016, Fenn wrote and published a children's book titled No Man's Land, about a boy who has autism. [52] She was inspired to write the book after her second son, Christian, was diagnosed with autism. [52]

Sherilyn got the starring role shortly after dyeing her beautiful long brown hair platinum blonde. “I was searching for things and I wasn’t looking within myself; I was looking on the outside, as we maybe do at twenty years old. Two days later, somebody called ma dumb blonde when I made a turn without signaling. It really stunned me. Then it sank in. Oh, yeah, I’m a blonde.”

O'Brien, Glenn (January 25, 2018). "When 'Twin Peaks' Actress Sherilyn Fenn Posed for Playboy". Playboy (Sweden). Her mother’s sisters, one of whom was Suzi Quatro, had an all-girl band. At one point, they lost their keyboard player and Sherilyn’s mom joined up. Sherilyn’s father managed the band. Mom served a two-year hitch until Suzi moved to England. She appeared in the 2007 Dukes of Hazzard prequel, The Dukes of Hazzard: The Beginning as Lulu Hogg. "It's just a fun silly role," Fenn said. But having already worked with director Robert Berlinger on Rude Awakening, she wanted to do so again. [49] Nominated for a Golden Globe Award for Best Performance by an Actress in a Supporting Role in a Series, Mini-Series or Motion Picture Made for TV – Twin Peaks Sherilyn Fenn, quoted in "Fenn de Siècle" by Joshua Mooney. Movieline. July 1993. pp. 36–40, 80–82.