Still, I did a lot of movies instead of waitressing or that kind of thing at the beginning, and it wasn't as if I even took acting very seriously when I started. I was in California for the first time. I was going to clubs, I was going here, I was going there, I was skipping acting classes when I could. Luckily, I had an agent who really believed in me and she just kept pushing me, thinking something would happen.
Fenn was born Sheryl Ann Fenn on February 1, 1965 in Detroit, Michigan. She comes from a family of musicians: her mother is keyboard player Arlene Quatro, her aunt is singer Suzi Quatro, her grandfather Art Quatro was a jazz musician, and her father, Leo Fenn, managed such rock bands as Suzi Quatro's The Pleasure Seekers, Alice Cooper, and The Billion Dollar Babies. Fenn is of Italian and Hungarian descent on her mother's side, and of Irish and French descent on her father's. She was raised Catholic.
Fenn began her career with a number of B-movies, including The Wild Life (1984, opposite Chris Penn), the 1986 skater film Thrashin' (opposite Josh Brolin and Pamela Gidley), the 1986 teen car action and revenge fantasy The Wraith (alongside Charlie Sheen and opposite Nick Cassavetes), the 1987 horror film Zombie High (alongside Virginia Madsen), and the Beauty and the Beast-inspired erotic movie Meridian. She had a part in the 1985 cult teen-comedy Just One of the Guys in which she tries to seduce a teenaged girl who was disguised as a boy, played by Joyce Hyser. Fenn starred alongside Johnny Depp in the 1985 short student film Dummies, directed by Laurie Frank for the American Film Institute. Fenn and Depp dated for three and a half years, subsequently getting engaged. In 1987, she joined Depp in a season-one episode of 21 Jump Street called "Blindsided".
Fenn dated pop singer Prince for a short time during 1985 and then Johnny Depp in 1986; their relationship lasted several years.
In the late 1990s, Fenn's career took a downturn. In 1993, she had stated:
In 1991, veteran Hollywood acting coach Roy London chose her to star in his directorial debut Diary of a Hitman, in which she plays a young mother determined to protect her child from hit man Forest Whitaker. According to Fenn, the turning point in her career was when she met London in 1990. She credits him with instilling confidence and newfound enthusiasm.
Fenn is the mother of two boys, born in 1993 and 2007.
In 1994, Fenn married guitarist-songwriter Toulouse Holliday, whom she met on the set of Three of Hearts.
After a short break during which she married and gave birth to a son, Fenn was chosen out of more than 100 actresses to portray Actress Elizabeth Taylor in NBC's 1995 telemovie Liz: The Elizabeth Taylor Story. Fenn called the role "probably the hardest job I’ve ever done." "Director Kevin Connor and I arranged a lunch, not an audition," said executive Producer Lester Persky. "We knew 10 minutes into our meeting that Sherilyn was it. She has the same striking beauty, and because of that she's experienced some of the things in life and in this Business that make Elizabeth such a fascinating person." When she accepted the part, Fenn was unaware that Taylor was embroiled in a lawsuit intended to stop both the broadcast of the film and the unauthorized biography that it was based on. Fenn stated about the controversy, "I am somebody who doesn't make choices lightly at this point of my life. I'm not somebody who wants to exploit another's woman story or life in any way." Fenn felt a kinship with Taylor, stating, "There are stereotypes of what a beautiful woman is. She struggled with that. A certain part of her life she went on that calling card. I certainly know I've come into contact with that. ‘You are too pretty,’ I'm told." During the shooting, Fenn supported the original screenwriter's effort to concentrate on Taylor the person, not the legend:
She then 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.
In a 1997 episode of Friends, "The One with Phoebe's Ex-Partner," which was Episode 14 of Season 3 of the show, Fenn guest-starred as Matthew Perry's girlfriend Ginger, who has a prosthetic right leg. She stated, "I like the show. I was happy to be a part of it."
Fenn again joined Jeremy Piven in a 1998 episode of Cupid, as Piven's love interest.
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." 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.
Following Rude Awakening, Fenn's work consisted of a number of episodic TV appearances. In the middle of the 2000s, she failed to find a role that could re-ignite her career as she got involved in many projects that went unrealized.
In 2001, she starred in The Outer Limits episode "Replica", playing a scientist who volunteered to be cloned. She also starred in an episode of Night Visions, as a woman who buys a used car possessed by a vengeful spirit. 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. However, the pilot was not ordered into a series.
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 then played the recurring part of Violet Montgomery on Fox's Boston Public (2003–2004), and appeared in Showtime's Cavedweller (2004) opposite Kyra Sedgwick.
In 2004, Fenn joined former co-star Mark Harmon in an episode of NCIS, as an amnesiac woman. She was afterwards cast for the 2004 remake of Mister Ed, planned for the Fox network—but after the pilot was shot, the show's writer/producer, Drake Sather, committed suicide, and the pilot was not aired.
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. The film was released in 2009 under the title Fist of the Warrior.
In 2005, Fenn made a notable appearance on The 4400, playing Jean DeLynn Baker, a 4400 who has the ability to grow toxin-emitting spores on her hands. She also guest-starred on the final episode of Judging Amy.
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. She subsequently joined its executive team in 2007 as executive Director of the film and television division.
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.
In July 2008, Fenn filmed The Scenesters, a black comedy made by Los Angeles-based comedy group The Vacationeers, which premiered in October 2009.
In July 2009, Fenn made a guest appearance on In Plain Sight as a lesbian counterfeiter.
In December 2010, Fenn appeared on Psych with other Twin Peaks actors on the season-five episode "Dual Spires" as sultry librarian Maudette Hornsby. The episode paid homage to Twin Peaks and also made many in-joke references to the show. She reprised her role as Audrey Horne in 2017 for the limited third season of Twin Peaks.
Fenn began practicing Transcendental Meditation in 2014.
In February 2016, she joined the cast of the American version of Shameless.
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. She was asked to read for the femme fatale Lola (eventually played by Young), but opted for the secretary role.
