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Robert Redford: 10 Great Roles

Our list has some surprising sleepers — and a few startling omissions

Robert Redford's Career Highlights

— The Everett Collection

Havana

Role: Jack Weil
Year: 1990

Redford did much of his best work with director Sydney Pollack, who, as a frequent actor himself, seemed most adept at helping his star explore regions beyond the screen image the public had come to expect. Redford is particularly out of his comfort zone here as a rough-edged professional gambler who goes to 1958 Cuba to make a killing in the casinos, but finds himself entangled with a beautiful woman (Lena Olin)  … and the Revolution. Redford can’t conceal his innate charm, but this is perhaps his most edgy acting job ever.

NEXT: He is haunted by waters

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