The daughter of Viva Hoffmann, better known simply as Viva, the model and Warhol protege, Gaby Hoffmann had an upbringing that was in many ways suited for the unconventional lifestyle that accompanies an acting career. Born January 8, 1982, in Pittsburgh, Hoffmann spent much of her childhood living with her mother and sister in New York's notorious Chelsea Hotel. When she and her friends weren't spying on the drug dealers across the hall, Hoffmann began her acting career, making her first commercials at the age of four to help pay the bills. However, she quickly tired of the work and quit; her early retirement ended when, at the age of seven, she was cast alongside Macaulay Culkin in John Hughes' Uncle Buck and as Kevin Costner's daughter in Field of Dreams. Both films proved to be huge hits, and Hoffmann decided to give acting a second try. Many of the films Hoffmann made throughout her early teens proved to be fairly forgettable, although she did have strong supporting roles in Nora Ephron's This Is My Life (1992) and Sleepless in Seattle (1993), as well as The Man Without a Face (1993), Now and Then (1995), which cast her as the teenage version of Demi Moore's character, and Woody Allen's Everyone Says I Love You (1996). Toward the end of the decade, Hoffmann began being identified as one of the up-and-coming actors of Generation Y, a fact that was demonstrated with her being cast in the ensemble film 200 Cigarettes, the controversial girls-on-top sex comedy Coming Soon, and James Toback's Black and White, which featured Hoffmann as part of an eclectic cast that included Robert Downey Jr., Jared Leto, and Brooke Shields.