Season 3 of the show, Fenn guest-starred as Matt LeBlanc's ex-girlfriend Ginger, who has a prosthetic right leg. She stated, "I like the show. I was happy to be a part of it." The same year, she was cast as the female lead in ABC's show Prey (originally entitled Hungry for Survival) and starred in the unaired original pilot episode. 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. Prey went on for one season before getting cancelled. 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" 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.M.J. Simpson. Interview With Sherilyn Fenn . October 1, 1997. Return to television: Rude Awakening (1998–2001) 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: 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 Farscapes 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. Fenn subsequently starred alongside Jon Tenney in the pilot for a remake of ABC's Love,