Although she garnered some attention at the outset of her Hollywood career, Virginia Madsen found her star eclipsed in the 1990s by her older brother Michael's jolting, thuggish performances for director Quentin Tarantino. After landing a plum role in the acclaimed 2004 indie Sideways, however, Madsen was showered with the kind of praise she'd been denied for nearly two decades in the business.

A native of the Chicago suburbs and the daughter of a PBS documentarian, Madsen learned her trade in city theater productions and summer performance camps. She made her way to Hollywood in the early '80s with her then-fiancé/fellow performer Billy Campbell. Making an inauspicious debut at the age of 19 as Andrew McCarthy's would-be first-time conquest in the teen sex comedy "Class", she would go on to more noteworthy roles in director David Lynch's sci-fi epic Dune and the slick but heartfelt romantic comedy "Electric Dreams" (both 1984). The rest of the decade wouldn't be quite as kind, as Madsen shuffled from part to part, appearing in a supporting capacity in both ambitious arthouse fare (1987's "Slamdance") and forgettable Hollywood comedies (1988's Hot to Trot and "Mr. North", the latter of which sparked a relationship with -- and three-year marriage to -- director Danny Huston). The beginning of the next decade fared somewhat better for Madsen. After a memorably brassy turn opposite Don Johnson in Dennis Hopper's steamy, seamy "The Hot Spot" (1990), she raked in some box-office cash in the minor horror hit Candyman (1992). Small performances in the high-profile, prestige pics Ghosts of Mississippi and The Rainmaker notwithstanding, Madsen all but disappeared from the late-'90s feature marketplace, as most of her films were either made for television or delivered directly to video-store rental shelves. Finding a more receptive outlet on weekly TV, Madsen snagged prominent recurring roles on NBC's "Frasier" and "American Dreams" around the turn of the century.

But it was writer/director Alexander Payne's low-budget character study Sideways that had Madsen clamoring for the ever-elusive "role of a lifetime." Payne was mostly unfamiliar with the actress' work, but her audition for the part of Maya -- a weary, contemplative divorcée with a fine-tuned taste for wine -- convinced him that she was the perfect complement to lead performer Paul Giamatti's high-strung sad sack Miles. Toning down her Hollywood glamour for the film, Madsen turned the small part into something of a revelation, and as reviewers showered praise upon the film in late 2004, the actress hauled in a truckload of awards from critics' groups as well as Golden Globe and Oscar nominations for Best Supporting Actress.

Although Madsen lost the Oscar bid to Cate Blanchett, high-profile offers rolled in after her Sideways coup. Early in 2006, she played Beth Stanfield, the wife of Harrison Ford's technology executive Jack Stanfield, in Richard Loncraine's disappointing hostage thriller Firewall; that summer, she also claimed an enigmatic part as a beguiling angel of death in Robert Altman's swan song, A Prairie Home Companion. Madsen began 2007 with two supporting turns in the same February weekend: in Michael Polish's The Astronaut Farmer, a quirky drama about a retired NASA astronaut turned farmer (Billy Bob Thornton) who builds a spacecraft in his barn; and in the higher-profile supernatural thriller The Number 23, playing wife to an unraveling Jim Carrey. ~ Michael Hastings, Rovi