In 2006, Fenn reteamed with Amy Sherman-Palladino and reappeared in the sixth and seventh seasons of Gilmore Girls as Anna Nardini, the ex-girlfriend of Luke Danes (played by Scott Patterson) and protective mother to his daughter April. Since the failure of the 2003 Gilmore Girls spin-off project, Sherman-Palladino had continued to want to work with Fenn again, and she wrote the character of Anna with her in mind. [44] When asked why she cast Fenn for two different roles on Gilmore Girls, Sherman-Palladino explained: Fenn gained newfound enthusiasm with the lead role in Showtime's sitcom Rude Awakening as Billie Frank, an alcoholic ex-soap opera actress, who tries to go sober and become a writer, but continues to struggle with her self-destructive habits. The series ran from 1998 to 2001 and co-starred Lynn Redgrave, Jonathan Penner, and Mario Van Peebles. She said of it:

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 Twin Peaks, Fenn chose to focus on widening her range of roles and was determined to avoid typecasting. She stated, "They've offered me every variation on Audrey Horne, none of which were as good or as much fun." [16] She turned down the Audrey Horne spinoff series that was offered to her, and unlike most of the cast, chose not to return for the 1992 prequel movie Twin Peaks: Fire Walk with Me, as she was then shooting Of Mice and Men. [17] Post- Twin Peaks roles (1992–1995) [ edit ] In 2020, Fenn attended the inaugural Fayetteville Comic Show along with numerous actors from Twin Peaks (James Marshall, Ray Wise, etc.) [62] David Walstad. "Legendary Portrayal." The Philadelphia Inquirer TV Week (US). May 21, 1995. pp. 4–5.She also had film roles in Wild at Heart (1990), Of Mice and Men (1992), Boxing Helena (1993), the television sitcom Rude Awakening (1998–2001), The United States of Leland (2003), Shameless (2016), and Shining Vale (2022). David Lynch, 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.

a b c d Walstad, David (May 21, 1995). "Legendary Portrayal". The Philadelphia Inquirer TV Week. US. pp.4–5. 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 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. a b Sherilyn Fenn, quoted in "Everybody's Mad about Sherilyn Fenn" by Jessica Sully, Movie (Australia). January 1993. pp. 18–20.Fenn played a crime boss in the 2002 film Swindle alongside Tom Sizemore. She had a small role in the film The United States of Leland alongside Ryan Gosling, in which she played a mother who captivates a troubled teenage boy.

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. Valcourt, Keith (December 8, 2016). "Sherilyn Fenn: 'Return to Twin Peaks' ". The Washington Times . Retrieved January 8, 2017. Now it's been almost two years since I started. I went to see David. We were drinking coffee, and I said, 'Oh this is wrong. And this.' He said, 'Sherilyn Fenn, you're a mess. You need TM!' He hooked me up with a wonderful teacher. It's life-changing. Fenn starred in the 1998 British psychological drama Darkness Falls as a wealthy and neglected wife, who is sequestered with her husband (played by Tim Dutton) by a man ( Ray Winstone) determined to understand the events that led to his wife ending up in a coma. Fenn called the film "a wonderful character piece" [15] While shooting the film in the Isle of Man in late 1997, Fenn considered settling in London to start a European career, but eventually decided to stay in the U.S. [17] [39] Return to television: Rude Awakening (1998–2001) [ edit ]She learned from her beloved teacher "to find the roles that you're passionate about, that speak to you on some level and which will help you grow on some level," [22] which has then become her line of conduct. "A lot of the sentiment that acting should be about an art form rather than mass entertainment and celebrity is at the core of Fenn's attitude to the business," wrote Jessica Sully in Australian magazine Movie. [23] "I try to keep myself centered," Fenn said. "I don't go to parties and all that. I don't think being seen or being in the right place is going to make me a better actress. I care about my work and try to do what's right in my heart." [24] As Mike Bygrave wrote in Sky Magazine: "One of the keys to understanding Fenn is that when she talks about the characters she plays she's really talking about herself." [25] Fenn was eager to play varied parts that could eclipse her sex-symbol image. "People who think they know me would be surprised that my whole life doesn't revolve around sex," she said. [21] After Twin Peaks, Fenn demanded a no-nudity clause in her contracts. She turned to independent films, choosing varied and unusual roles: a b "Sherilyn Fenn | Photography Steven Meisel | Dolce & Gabbana Ad Campaign | Fall/Winter 1991/1992". Strip Project (in Italian). August 27, 2015 . Retrieved February 2, 2021. James Marshall, quoted in "The James Marshall Interview" by Craig Miller and John Thorne. Wrapped in Plastic. Issue 72. December 2004. Sherilyn Fenn, quoted in "The Rise and Thrall of Sherilyn Fenn" by James Steranko Prevue (US). March 1991. pp. 42–43, 53, 57. Jensen, Jeff (March 23, 2017). "This Week's Cover: Exclusive details on the Twin Peaks revival". Entertainment Weekly.