1992–98: Early acting roles and Prefontaine
Leto at a press conference for My So-Called Life in 1995
In 1992, Leto moved to Los Angeles to pursue a career in directing, intending to take acting roles on the side.[16] He found minor roles on television shows but his first break came in 1994, after he was cast opposite Claire Danes as Jordan Catalano, her love interest, in the short-lived but well-reviewed ABC teen drama My So-Called Life.[7] The show was praised for its portrayal of adolescence and gained a strong cult following, despite being canceled after only one season.[17] The same year, he made his television film debut starring alongside Alicia Silverstone in Cool and the Crazy, and landed his first film role in the 1995 drama How to Make an American Quilt. He later co-starred with Christina Ricci in The Last of the High Kings (1996) and got a supporting role in Switchback (1997).[15]
In 1997, Leto starred in the biopic Prefontaine in which he played the role of Olympic hopeful Steve Prefontaine. For the preparation of the role, Leto immersed himself in the runner's life, training for six weeks and meeting with members of his family and friends.[18] He bore a striking resemblance to the real Prefontaine, also adopting the athlete's voice and upright running style.[19] His portrayal received positive reviews from critics and is often considered his breakthrough role.[20][21] Peter Stack of the San Francisco Chronicle noted how Leto played the athlete with raw vitality; "With hypnotic blue eyes and dirty blond hair, Leto captures the rock-star style Prefontaine affected, and he looks natural in fiery performances on the track, as well as off, where Pre affected a brash, confrontational style."[22]
After landing the lead role of a British aristocrat in the 1998 drama Basil, Leto starred in the horror Urban Legend. The film was poorly received by most movie critics, however, it was a financial success.[23][24] The same year, Terrence Malick cast Leto for a supporting role in the war film The Thin Red Line alongside Sean Penn and Adrien Brody.[25] It garnered mostly positive reviews and was a moderate success in the box office.[26] It received multiple awards and nominations, including seven Academy Award nominations; Leto shared a Satellite Award with the rest of the cast.[27][28]