She also had film roles in Wild at Heart (1990), Of Mice and Men (1992), Boxing Helena (1993) and The United States of Leland (2003) and appeared in the television series Rude Awakening (1998–2001), Shameless (2016), and Shining Vale (2022).

Her father, Leo Fenn, managed rock bands including Suzi Quatro's The Pleasure Seekers, Alice Cooper, and The Billion Dollar Babies.

[4] Not wanting to start with a new school again, Fenn dropped out after her junior year and decided to pursue acting, enrolling at the Lee Strasberg Theatre Institute.

Fenn’s breakthrough came when she was cast by David Lynch and Mark Frost as the tantalizing, reckless Audrey Horne, a high school femme fatale, in the TV series Twin Peaks, which ran between 1990 and 1991.

The character of Audrey was one of the most popular with fans, in particular for her unrequited love for FBI Special Agent Dale Cooper (played by Kyle MacLachlan) and her style from the 1950s (with her saddle shoes, plaid skirts, and tight sweaters).

[4]Shortly after shooting the Twin Peaks pilot episode, David Lynch gave her a small part in Wild at Heart, as a girl injured in a car wreck, obsessed by the contents of her purse, alongside Nicolas Cage and Laura Dern.

[3] 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.

[15] After two nominations (Emmy and Golden Globe) for Twin Peaks, and the pictorial in Playboy, Fenn was propelled to stardom and became a major sex symbol, with her Old Hollywood looks.

In October 1990, while promoting Twin Peaks, Fenn made the cover of Rolling Stone magazine along with Mädchen Amick and Lara Flynn Boyle.

"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.

Fenn portrayed a narcissistic seductress amputated and imprisoned by Julian Sands, who makes her become his personal Venus de Milo in an effort to possess her.

"[15] She then starred in Carl Reiner's neo-noir parody Fatal Instinct as Armand Assante's devoted secretary and Sean Young's and Kate Nelligan's rival.

[29] Fenn afterward portrayed Potiphar's wife Zulaikha in Showtime's 1995 Biblical TV movie Slave of Dreams opposite Adrian Pasdar and Edward James Olmos.

"[20] During the shooting, Fenn supported the original screenwriter's effort to concentrate on Taylor the person, not the legend:[20] I fought to keep the integrity of the story because the producer was bringing in a writer that was making it very soapy.

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.

However, after the filming was done and post-production work almost wrapped up, the studio heads abruptly changed course, replacing Fenn with Debra Messing and reshooting the entire pilot.

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.

"[15] 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.

Fenn subsequently starred alongside Jon Tenney in the pilot for a remake of ABC's Love, American Style, for the 1998–1999 television season.

Guest stars include Mariska Hargitay, Steven Eckholdt, Fenn, Jon Tenney, Melissa Joan Hart, Matt Letscher, Joely Fisher, Tom Verica, and writer/producer Winnie Holzman (My So-Called Life).

She was cast as a kindergarten teacher for the pilot of the 2001 American version of the British TV show Blind Men, alongside French Stewart.

[34] She also played a manipulative woman in a season-four episode of Law & Order: Special Victims Unit versus both Christopher Meloni and Mariska Hargitay, and appeared in Watching Ellie.

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.

In 2004, Fenn co-starred opposite Traci Lords and Paul Johansson in Emily Skopov's Novel Romance, released in 2006, in which she played a pregnancy shop owner who herself cannot have children.

She then appeared in the martial arts film Lesser of Three Evils alongside Ho Sung Pak, Peter Greene, and Roger Guenveur Smith, as the unbalanced and alcoholic wife of a corrupt detective.

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.

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.

[43] In July 2006, shortly after shooting The Dukes of Hazzard prequel, Fenn stepped behind the camera for the first time and directed in Pittsburgh a documentary film about child enrichment program CosmiKids and its founder, Judy Julin.

In December 2010, Fenn appeared on Psych with other Twin Peaks actors on the season 5 episode "Dual Spires" as sultry librarian Maudette Hornsby.

In 2022, Sherilyn portrayed Sarah Jane McCubbin, a widow with dementia who plans to be euthanized by her mentally imbalanced son in the psychological drama Losing Addison.