Returning to the U..S., he enrolled as an art student at Brooklyn's Pratt Institute and at the same time began training as an actor at the American Academy of Dramatic Arts. He made his Broadway debut in 1959, playing a minor supporting role in "Tall Story". His stage parts gradually increased in importance and culminated in 1963 in the starring role in the Broadway romantic comedy hit "Barefoot in the Park".

During the early 60's, he also appeared on TV in segments of such shows as "Playhouse 90", "Twilight Zone", and "Alfred Hitchcock Presents". After an isolated screen role in 1962, he began appearing regularly in films in 1965, initially playing standard pleasant leads in routine films. He was catapulted to the top in 1969 as a result of the great commercial success of Butch Cassidy and the Sundance Kid, in which he proved an excellent match in the Kid role to Paul Newman's Butch. The two stars were teamed again, even more successfully, in the 1973 blockbuster The Sting, for which Redford was nominated for an Oscar. By then the blue-eyed, blond Redford had surpassed Newman in the box-office popularity rankings, thanks to appealing performances in such films as Downhill Racer (1969), The Candidate, Jeremiah Johnson (1972) and The Way We Were (1973).

By 1974 he was America's number one crowd pleaser, popular among female audiences for his manly, open-faced handsomeness and among males for his convincing portrayals of square-jawed, sky-eyed, loner heroes. Before long, he established his own production company, Wildwood Enterprises, through which he became instrumental in bringing to the screen All the President's Men (1976), the story of the Watergate investigation, in which he portrayed Washington Post reporter Bob Woodward. He scored a success with his first attempt in directing, winning an Academy Award as Best Director for Ordinary People (1980). He continued to impress with his directorial talent in The Milagro Beanfield War (1988); the well-regarded documentary of a Native American demonized by the FBI, Incident at Oglala (1992); and, in the same year, with the film adaptation of the best-selling novel A River Runs Through It.

Though Redford has always been extremely selective in his acting roles, he has grown even more cautious since the 80's with some disappointing (Havana) and some commercially successful (Indecent Proposal) results.

Off-screen, Redford is known as a dedicated outdoorsman and a versatile, daring athlete who indulges abundantly in many sports, from tennis and horseriding to skiing, motor racing, and air gliding. A dedicated conservationist, he maintains a home in Manhattan and offices in Hollywood, but spends much of his time in Utah, where he owns vast stretches of wild land, encompassing a ranch, a quarter-horse training farm, and the famous Sundance Ski Resort. In 1980, Redford founded the Sundance Institute, a workshop and training ground for young filmmakers, and the site of the United States Film Festival.