An uncredited role in 1993's "Army of Darkness" marked the beginning of Featherstone's acting career. The following year she starred in the little-seen thriller "Dark Angel". While the film was largely panned or ignored by critics, the young actress emerged unscathed, having turned in a strong and inspired performance as a beautiful mistress of the underworld on a justice-serving rampage. A supporting role in 1996's drama "illtown" followed, and she increased her visibility with appearances in "Con Air" (1997) and "Half Baked" (1998). Featherstone was featured prominently as Ben Stiller's neglected and frustrated live-in girlfriend in Jake Kasdan's engaging comic mystery "Zero Effect" (1998). That same year, decked out in 1980s garb, the actress took a turn in the popular romantic comedy "The Wedding Singer" as the woman who leaves Adam Sandler at the altar. She revisited that decade as part of the ensemble of 1999's "200 Cigarettes", playing a woman determined to score a date on New Year's Eve 1981, even if it means double-crossing her friend (played by Nicole Parker). Next up was a supporting role in the computer hacker thriller "Takedown" (also 1999).

Having previously appeared in a guest role on a 1993 episode of the quirky CBS series "Northern Exposure", Featherstone made her television series debut as a regular as Detective Hannah Tyler on ABC's crime drama "Cracker" (1997-1998). While this US adaptation of the popular British series was short-lived, her work opposite Robert Pastorelli's criminal psychologist Gerry 'Fitz' Fitzgerald was noteworthy. She played both strong and vulnerable in a particularly interesting and multi-layered role as Fitz's insecure colleague and object of extramarital affection, proving a capable performer and compelling presence. She was additionally featured on the small screen with memorable guest appearances, including a 1997 recurring role on "Friends" as Chloe, the "Xerox girl" with whom David Schwimmer's Ross "cheated" on Jennifer Aniston's Rachel. Featherstone was also featured as the maid Jerry falls for in a 1998 episode of "Seinfeld". Her next TV role would be played out behind the scenes, as a producer for a DreamWorks sitcom picked up by NBC.