Childhood & Early Years
Sherilyn was born Sheryl Ann Fenn, on February 1, 1965, in Detroit, Michigan, into a family of musicians. Her mother, Arlene, was part of the all-girl Quatro sisters band ‘The Pleasure Seekers,’ with her famous rockstar-bassist sister Suzi Quatro. Her father, Leo Fenn, managed the band and other famous 1970s rockers, such as Alice Cooper.’ Sherilyn’s grandfather, Art Quatro, played jazz with the 'Art Quatro Trio.’
She grew up in Grosse Pointe, Michigan, and was raised according to Catholic beliefs. Sherilyn is of half-Italian and half-Hungarian descent from her mother's side. Her father is of Irish, Bohemian-Czech, German, and English ancestry. Her mother’s Italian family name, “Quatro,” is short for “Quatroccio.”
As a kid, she traveled a lot with her mother and brothers, until they settled down in Los Angeles. She was 17 then and did not want to join a new school. She was intimidated by the idea of going to ‘Beverly Hills High’ and convinced her mother to let her pursue acting lessons instead. Thus, she dropped out after her junior year and enrolled at the ‘Lee Strasberg Theatre Institute.’
Sherilyn was also averse to the idea of going to college and thought it was “an extended vacation.” Thus, at 18, she started auditioning. She landing modeling and acting jobs soon and continued to get steady work until the late 1990s.
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Fenn got her first taste of the entertainment industry while touring the country with her mother. At 19, she used her stunning appearance to become a ‘Playboy Bunny’ in Los Angeles for 2 months.
After sundry modeling jobs for perfumes and designer jeans, she made her debut in ‘The Wild Life’ (1984) and then appeared in a number of similar B-movies, such as the skating extravaganza ‘Thrashin'’ (1986), opposite Josh Brolin; the teen revenge-fantasy ‘The Wraith’ (1986), alongside Charlie Sheen; the horror ‘Zombie High’ (1987); and the ‘Beauty and the Beast’-inspired erotic flick ‘Meridian’ (1990).
She later accused several of her early films, including her first-ever starring role in ‘Two Moon Junction’ (1988), of “sexploitation”. It was meant to be her big break, but she later claimed that she was "so embarrassed about how it turned out that I went into a cocoon for a year afterwards." After these experiences, she decided to take control of her career and vowed "not to be pushed into what other people wanted me to be."
Fenn skyrocketed to fame in the early 1990s, with David Lynch and Mark Frost’s ‘ABC’ series ‘Twin Peaks’ (1990), playing a tantalizing and reckless high-school “femme fatale.” Soon, Lynch gave her a small role akin to "a broken China doll," in ‘Wild at Heart’ (1990), alongside Nicolas Cage and Laura Dern. The film won the ‘Palme d'Or’ at the ‘Cannes Film Festival’ in 1990.
She was then seen in ‘ABC's gangster telefilm ‘Dillinger’ (1991), opposite Mark Harmon, the huis-clos ‘Diary of a Hitman’ (1991), and the neo-noir black comedy ‘Desire and Hell at Sunset Motel’ (1992, initial release: May 1991, UK).
Fenn became wary of being typecast and turned down an Audrey Horne spin-off series and the prequel ‘Twin Peaks: Fire Walk with Me,’ choosing Gary Sinese's version of ‘Of Mice and Men’ (1992) instead. She also replaced Kim Basinger in Lynch junior’s ‘Boxing Helena,’ one of her most notable roles.
By now, she was demanding no-nudity clauses in her contracts and turning to independent films to prove her mettle. She was part of the fictionalized Jack Ruby biopic ‘Ruby’ (1992). She had a disagreement with director Yurek Bogayevicz while working in the romantic comedy ‘Three of Hearts’ (1993), as she refused to appear nude in the film.
Following this, she appeared in Carl Reiner's parody ‘Fatal Instinct’ (1993) and ‘Showtime's biblical TV movie ‘Slave of Dreams’ (1995). She also starred in an episode of ‘Tales from the Crypt’ in 1995, directed by Robert Zemeckis. The apex of her career in the 1990s, however, was her performance as Elizabeth Taylor in the TV biopic ‘Liz: The Elizabeth Taylor Story’ (1995).
After her guest appearance as ‘Chandler's girlfriend in a 1997 episode of the sitcom ‘Friends,’ Fenn did independent films such as Feldman's ‘Lovelife’ (1997), the romantic comedy ‘Just Write’ (1997), and the neo-noir ‘Othello’ adaptation ‘Cement’ (2000).
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Disillusioned with Hollywood, she contemplated moving to Europe after starring in the British psychological drama ‘Darkness Falls’ (1999). However, she eventually returned to a leading role in ‘Showtime’s dark-comedy series ‘Rude Awakening’.
She was seen in the science-fiction horror ‘The Outer Limits’ (2001), the family comedy ‘Off Season’ (2001), ‘Law & Order: Special Victims Unit’ (2002), ‘Dawson's Creek’ (2002), ‘Boston Public’ (2003–2004), and a 2003 episode of ‘Gilmore Girls,’ with a return to the show in a different role in its 2006–2007 season.
She also appeared in ‘The United States of Leland’ (2003), alongside Ryan Gosling; ‘Showtime's ‘Cavedweller’ (2004); the science fiction ‘The 4400’ (2005); the race-relations drama ‘Whitepaddy’ (2006); Emily Skopov's ‘Novel Romance’ (2006); the psychological thriller ‘Presumed Dead’ (2006); ‘The Dukes of Hazzard: The Beginning’ (2007); the black comedy ‘The Scenesters’ (2009); and ‘In Plain Sight’ (2009, cameo).
In December 2010, Fenn appeared in a ‘Psych’ episode titled ‘Dual Spires,’ with other ‘Twin Peaks’ actors, making many humorous references to the show. Since then, she has appeared in innumerable one-episode cameos and supporting roles in telefilms, animations, indies, and shorts.
She then came back in recurring roles in ‘Showtime’s award-winning dramas, first in the second season of the ‘Golden Globe’-winning series ‘Ray Donovan’ in 2014 and then in ‘Shameless’ in February 2016.
In 2017, she reprised her character for the limited third season of ‘Twin Peaks,’ aptly titled ‘The Return.’ It was mired in script and production issues and received divided reviews from critics and limited success on TV. However, it was hailed by the franchise's longtime fans as yet another Lynch classic.
Fenn has had recent stints in the ‘CBS’ series ‘S.W.A.T.’ and the ‘Amazon’ series ‘Goliath.’ Her upcoming projects include a Vladislav Kozlov short, ‘The Killers’ (2019), and a film on Rudolph Valentino, the Hollywood silent-screen icon, titled ‘Silent Life,’ currently being filmed and set for completion in 2020. She is also set to appear in the 2019 indies ‘Shooting Heroin,’ ‘Something About Her,’ and ‘For Entertainment Purposes Only,’ all currently in the post-production stage.
She lent her voice to the characters of ‘Katara’ and ‘Mama Dinosaur’ in ‘Robot Chicken.’
Family & Personal Life
Fenn dated pop megastar Prince for a short while in 1985. In 1986, she dated and eventually got engaged to actor Johnny Depp. They had met on the sets of their short film ‘Dummies’ and also starred opposite each other in the ‘21 Jump Street’ episode ‘Blindsided’ in 1987. The relationship lasted 3.5 years.
The sultry actor has had several flings during her early years. She has been romantically linked with her ‘The Wild Life’ co-star Chris Penn. She has also been associated with Barry Hollywood, who had photographed her for the December 1990 issue of ‘Playboy’ magazine.
On December 4, 1994, Sherilyn married guitarist-songwriter and film technician Toulouse Holliday, whom she had met while filming ‘Three of Hearts.’ They divorced in 1997 but have maintained their friendship since. They have a son, Myles Holliday, born in their Los Angeles home on December 15, 1993.
Her current partner is Dylan Stewart, a ‘Macintosh’ consultant and son of writer-director Douglas Day Stewart. With him, she had her second son, Christian James, on August 6, 2007.
She has published a children’s story book, ‘No Man’s Land,’ inspired by her younger son, who is reportedly on the autism spectrum. She has also been busy writing her memoirs.
In a March 2019 incident, Fenn lost everything in a fire at her apartment complex. She mentioned in an interview that though she is not too attached to material possessions, it was hard letting go of her children’s pictures.