A native of West Orange, New Jersey, Pitt announced to his parents that he wanted to be an actor when he was ten years old. His folks scraped together the money to send him to an acting school and age 16, the aspiring performer crossed the Hudson and settled in NYC. Sustaining himself as a bike messenger, Pitt began landing roles, including a bit part on the ABC soap "All My Children", a guest spots on "Dellaventura" and "Law & Order" as well as roles in student films and the occasional independent production (e.g., "54" and "The Hi-Life" both 1998). He made his Off-Broadway debut in 1999 in the Depression-era drama "The Trestle at Pope Lick Creek". Pitt earned generally positive notices for his performance as an impressionable young man who comes under the spell of a slightly older woman (Alicia Goranson), A casting agent spotted the actor—who bears a slight resemblance to Leonardo DiCaprio—and suggested him for the "Dawson's Creek" role.
Since he found the TV work financially rewarding but artistically unimpressive, Pitt segued to supporting roles in mainstream films. Director Gus Van Sant tapped him to play the preppy pal of Anna Paquin and newcomer Rob Brown in "Finding Forrester" (2000) and novice helmer Faye Dunaway cast him in her directorial debut "The Yellow Bird" (lensed 2000), which is set to air on the WE Network. Pitt saw his profile rise with his strong turn as Tommy, a military brat with singing aspirations who becomes a rock star under the tutelage of an East German transsexual in the terrific musical film "Hedwig and the Angry Inch" (2001). which premiered to rapturous acclaim at Sundance. Pitt's good looks, charisma and acting ability tagged him as one to watch. He solidified his rising star status with a chilling but humorous performance as a perpetually drugged out Florida teen who goes along with his girlfriend when she agrees to participate in a murder in the disturbing "Bully" (also 2001). He followed by co-starring with Sandra Bullock in the thriller "Murder by Numbers" (2002).
In the psychological drama, “Rhinoceros Eyes” (2003), Pitt played an eccentric recluse, Chep, who works at a prop house and is smitten with a set designer (Paige Turco) whose requests for objects become increasingly bizarre. Chep loses touch with reality when he begins to resort to drastic—and often violent—means to obtain props for his unrequited love. After playing an American exchange student caught in the midst of the ’68 Paris riots and an unusual love triangle in “The Dreamers” (2003), Pitt had a small role in “The Village” (2004), M. Night Shyamalan’s predictable thriller about a 19th-century village held at bay by a race of strange forest creatures surrounding their idyllic town. Pitt then reunited with Van Sant for a fictional recounting of troubled rock star Kurt Cobain’s decline and fall in “Last Days” (2005). Playing an increasingly pressured and isolated artist, Blake, Pitt gave a fine turn in a film that borrowed liberally from Cobain’s tortured life.