While struggling in Los Angeles, Pitt took on various occasional jobs. These jobs ranged from chauffeur, to dressing up as an El Pollo Loco chicken to pay for his acting classes.
He began studying with acting coach Roy London.
Brad Pitt began his onscreen acting career in 1987 with uncredited parts in the films No Way Out, No Man's Land, and Less Than Zero.
He made his television debut with a guest appearance on the American ABC sitcom Growing Pains. Between December 1987 and February 1988 he appeared in four episodes of the CBS primetime soap opera Dallas, portraying Randy, the boyfriend of Shalane McCall's character, Charlie Wade. Pitt described the character as "an idiot boyfriend who gets caught in the hay".
He later said about his scenes with McCall: "It was real sweaty-palms time for me. It was kind of wild, because I'd never even met her before." Pitt made a guest appearance on the FOX police drama 21 Jump Street later in 1988.
Furthermore in the same year, he performed in his first leading role within a film, The Dark Side of the Sun, a Yugoslavian-U.S. co-production. He portrayed a young American taken by his family to the Adriatic to find a remedy for a skin condition. The film was shelved due to the outbreak of the Croatian War of Independence and was not released until 1997.
In 1989, Pitt appeared in two motion pictures. The first was in a supporting role in the comedy Happy Together, and the second was in a featured role in the horror film Cutting Class, his first film to reach theaters.
He also made television guest appearances on Head of the Class, Freddy's Nightmares, Thirtysomething, and (for a second time) Growing Pains.
Pitt was cast in the NBC television movie Too Young to Die? in 1990, a story about an abused teenager given the death penalty for murder. Pitt portrayed the part of Billy Canton, a drug addict who takes advantage of a runaway young woman, portrayed by Juliette Lewis. Entertainment Weekly's film reviewer wrote: "Pitt is a magnificent slimeball as her hoody boyfriend; looking and sounding like a malevolent John Cougar Mellencamp, he's really scary."
That year, he also co-starred in the short-lived FOX dramatic series Glory Days, a stint that lasted for six episodes, and appeared in a supporting role in the HBO television movie The Image.
Pitt's next onscreen appearance was in the 1991 film Across the Tracks; he portrayed Joe Maloney, a high school runner. The character deals with his criminal brother, played by Ricky Schroder.
Pitt soon attracted broader public attention with a supporting role in the 1991 road film Thelma & Louise. He portrayed J.D., a small-time criminal who befriends Thelma (Geena Davis). His love scene with Davis has been cited as the moment that defined Pitt as a sex symbol.
After the success of Thelma & Louise, Pitt starred opposite Catherine Keener and Nick Cave in Johnny Suede (1991), a low-budget film about an aspiring rock star.
In 1992, he appeared in Cool World, before starring as Paul Maclean in Robert Redford's 1992 biographical film A River Runs Through It; his portrayal of the character has been described as a "career-making" performance, admitting that he felt a "bit of pressure" when making the film. He added that it was one of his "weakest performances ... It's so weird that it ended up being the one that I got the most attention for." When asked about working with Redford, Pitt said, "It's like tennis: When you play with somebody better than you, your game gets better."
Pitt reunited with his Too Young to Die? co-star Juliette Lewis in the 1993 road film Kalifornia by portraying Early Grayce, a serial killer and the boyfriend of Lewis's character. In his review of the film, Rolling Stone's Peter Travers described Pitt's performance as "outstanding, all boyish charm and then a snort that exudes pure menace". Later that year, Pitt won a ShoWest Award for Male Star of Tomorrow.
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