A regular on ABC's short-lived series "Camp Wilder" (1992-93), likewise on ABC's even more brief "Leaving L.A." (1997), Swank gained some notice when she joined the cast of Fox's popular "Beverly Hills, 90210" in 1997 playing a single mom who served as a love interest for Ian Ziering's character, Steve. Roles in the straight-to-video releases "Sometimes They Come Back. . . Again" (1994) and "Kounterfeit" (1997), however, did little to raise her profile, nor did her work in the telefilms "Terror in the Family" (Fox, 1996) and "Dying to Belong" (NBC, 1997).

Her lack of name recognition aided Swank in landing the career transforming role of Teena Brandon, a Nebraska woman who opts to live as a man, in "Boys Don't Cry" (1999). Based on a true story and beautifully realized by director Kimberly Peirce, the film presented numerous challenges for Swank. Having successfully passed the audition, she cut off her long hair and worked with a trainer to build the requisite muscle. As part of her extensive preparation, she created a male alter ego and spent close to a month living in that persona in Los Angeles, a move that provided the actress with plenty of first-hand research. The onscreen results were astonishing—she conveyed the swagger and fragility of the character, with many praising her performance as one of the year's best. Swank earned many accolades, including an Academy Award for Best Actress.

Now one of Hollywood's It girls, Swank fielded numerous offers, opting to take the role of an abused wife in the ensemble of Sam Raimi's Southern Gothic "The Gift" (2000) before undertaking the lead role as a French noblewoman in the period drama "The Affair of the Necklace" (2001). She continued to chose her roles carefully, next appearing in 2002's eerie Alaskan thriller "Insomnia" with Al Pacino and Robin Williams, and directed by Christopher Nolan of “Memento” (2000) fame. She was next seen alongside Aaron Eckhart in the sci-fi thriller "The Core" (2003), a contrived disaster flick about the impending destruction of the earth after its core mysteriously stops rotating. Though trailers were pulled after the Space Shuttle tragedy, the movie would have flopped regardless on its own accord.

Just as she was beginning to appear to be the recipient of an early-Oscar-win curse, Swank rebounded with a strong performance in the widely praised HBO suffragette telepic "Iron Jawed Angels" (2004)—for which she earned a Golden Globe award nomination for Best Actress in a Leading Role – Mini-Series or Television Movie. She then appeared in “Million Dollar Baby” (2004), an engrossing drama that some have called one of director Clint Eastwood's best films. As Maggie Fitzgerald, a tough and determined but undisciplined female boxer looking for someone to believe in her, Swank both carved her body into a taughtly-muscled fighting machine and wore her character's emotions openly, delivering her most compelling performance since her breakout in "Boys Don't Cry." The role earned the actress a slew of important accolades, including a Golden Globe award win for Best Performance by an Actress in a Motion Picture – Drama and a Screen Actors Guild Award triumph, culminating with her second Oscar victory for Best Actress in a Leading Role.

Swank next costarred in costar in “The Black Dahlia” (2006), Brian De Palma’s take on James Ellroy’s complicated and richly-textured noir thriller about two hard-edged cops (Josh Hartnett and Aaron Eckhart) who descend into obsession, corruption and sexual degeneracy as they investigate the brutal murder of would-be actress Elizabeth Short (Mia Kirshner), who was found tortured and vivisected in a vacant lot in Los Angeles. Swank had the unusual experience of being the femme fatale, playing the seductive Madeleine Linscott, a dead-ringer for Short who becomes the source of wild fascination for one of the detectives. She next starred in “Freedom Writers” (2007) as Erin Gruwell, a dedicated California teacher who unified her disadvantaged, racially-challenged students by having them keep journals about their troubled and often violent lives. Then in “PS, I Love You” (lensed 2006), Swank was a grieving young widow who discovers that her dead husband left a list of tasks delivered in 10 messages in order to help ease her out of grief and into a new life.