Robert Redford's most memorable roles

Robert Redford is responsible for some of the most memorable films of the last 50 years. The actor's career as a movie star has spanned from the 1960s to the 2010s, when he announced his retirement from acting, and his directorial efforts like Ordinary People and Quiz Show garnered critical and commercial acclaim.

Redford's impeccable good looks and steady, confident demeanor cemented him as one of the defining stars of his generation, equally capable of lending levity and gravitas to lighthearted entertainment and heavy, thoughtful dramas alike. Join us as we look back on some of his best performances and directorial works.

Robert Redford Roles — Robert Redford in 'Butch Cassidy and the Sundance Kid,' 'All the President's Men,' and 'The Horse Whisperer'. Mary Evans/Ronald Grant/Everett; Everett; Buena Vista/Everett

01 of 20

This Property Is Condemned (1966)

THIS PROPERTY IS CONDEMNED, from left: Robert Redford, Natalie Wood, 1966 — This Property is Condemned. Courtesy Everett

In some ways, Robert Redford owed his earliest stardom to Natalie Wood, who starred opposite him in 1965's Inside Daisy Clover. Wood had director and co-star approval over This Property Is Condemned, an adaptation of a one-act Tennessee Williams play of the same name, and she chose Redford after forming a friendship with him on Clover. Redford stars as Owen Legate, an employee of the railroad company who comes to Alva's (Wood) small town to close the train depot there. Redford and Wood share a star-crossed romance as Alva and Owen, her fragility tempered by his straightforward manner. Redford also recruited his friend Sydney Pollack to direct the film, thus launching Pollack's career as well. The two men cobbled together the script, which had already gone through numerous drafts with multiple writers, including a young Francis Ford Coppola. Though it wasn't well-reviewed at the time, it helped secure Redford's leading man status and displayed his crackling, heartbreaking chemistry with Wood.—Maureen Lee Lenker

02 of 20

Barefoot in the Park (1967)

The original Barefoot in the Park play, directed by Mike Nichols and debuting on Broadway in 1963, marked Redford's breakout moment as an actor. He starred as Paul, the stuffy newlywed who finds his life and relationship descending into comic mayhem due to the neighbors and living situation at his new apartment. Redford reprised the role in the film adaptation, with Jane Fonda starring as Paul's vibrant wife, Corie. The film is considered one of the best adaptations of Neil Simon's work, and Redford gets to immortalize his subtly comedic take on marriage that earned him notice on the Broadway stage. Not to mention, he has stellar chemistry with Fonda that sparks as the story hurdles to its hilarious conclusion. —Maureen Lee Lenker

03 of 20

Butch Cassidy and the Sundance Kid (1969)

If there's any film that can be credited with truly making Redford a star, it's Butch Cassidy and the Sundance Kid, a Western fable of two outlaws, leader Butch Cassidy (Paul Newman) and the stoic Sundance Kid (Redford). Directed by George Roy Hill, the movie is as much as parable of Vietnam disillusionment as it is a story of the death of the Old West and the American mythology surrounding it. Redford and Newman forge an indelible screen duo (a pairing they sadly only repeated one other time), as the two joke, hustle, and shoot their way out of one hairy situation after another. Redford also romances Katharine Ross' Etta, creating an iconic trio with Newman as tender third wheel. The script by legendary scribe William Goldman is one of the best ever written, and it's Redford who gets many of the film's funniest glib one-liners, all the while maintaining Sundance's image as the strong, silent type. With the assistance of Edith Head's masterful, rugged costume designs and Conrad L. Hall's evocative cinematography, the film shot Redford to instant heartthrob status. But its most crucial legacy may just be its freeze-framed final shot, as fitting an epitaph as any actor will ever receive. —Maureen Lee Lenker

04 of 20

The Candidate (1972)

In The Candidate, a searing satire of American politics, Redford plays Bill McKay, the Democrat son of a former governor who is selected to run an unwinnable campaign against an incumbent Republican senator. Redford is the perfect actor to play a politician, as he brilliantly embodies a character arc we see in virtually every major election: his candidate starts with starry-eyed idealism that's gradually chipped away until he's left with almost no concrete convictions, doing whatever it takes to stay in the race. The actor's desperate, befuddled delivery of the film's last line makes for one of the most effective finales of his career. — Wesley Stenzel

05 of 20

The Way We Were (1973)

Considered one of the greatest love stories of American cinema, The Way We Were chronicles the ill-fated romance of preppy WASP Hubbell (Redford) and the Jewish, staunchly anti-war Katie (Barbra Streisand). The bittersweet story follows their relationship over the course of many years, from their first meeting in college to their reunion following World War II through to the strain of the Communist witch hunt of the Hollywood Blacklist. Only Redford could manage to make a callous, entitled character like Hubbell so irresistible, and despite his own reservations about the project, it enshrined him as a romantic leading man of the highest order. Combined with Streisand's rendition of the Oscar-winning title song, The Way We Were remains a tearjerker guaranteed to make audiences swoon. —Maureen Lee Lenker

06 of 20

The Sting (1973)

THE STING, Robert Redford, 1973 — The Sting. Everett Collection

The actor reteamed with Butch Cassidy co-star Newman and director Hill for the smash-hit crime caper. The film won the Oscar for Best Picture and was second to only The Exorcist at the 1973 box office. While Butch Cassidy cast the duo as rugged outlaws on their last legs, The Sting allows Redford and Newman to fully embrace their endless movie star charisma as their characters charm their way through elaborate cons. Redford earned his only acting Oscar nomination for his turn here. — Wesley Stenzel

07 of 20

All the President's Men (1976)

Ask a journalist what movie made them want to become a reporter, and odds are it'll be All the President's Men. Redford stars as real-life reporter Bob Woodward opposite Dustin Hoffman as Carl Bernstein, the two Washington Post journalists who uncovered the Watergate scandal and helped bring down the presidency of Richard Nixon. Redford followed the case closely from its earliest days and bought the rights to Woodward and Bernstein's book in 1974. As an executive producer of the film, it was Redford who recruited Butch Cassidy scribe William Goldman to write the screenplay, and the actor was also involved in Alan J. Pakula's hiring as director and in Hoffman's casting. Nominated for eight Oscars, it lost Best Picture to Rocky, a decision many Academy Members have since said they regret. The film helped establish the ways in which Redford's projects reflect his political concerns offscreen. Its timely depiction of investigative journalism and government corruption make for a memorable thriller that endures as the gold standard of movies about the press. —Maureen Lee Lenker

08 of 20

Ordinary People (1980)

Redford's directorial debut, Ordinary People, cast Donald Sutherland, Mary Tyler Moore, and Timothy Hutton as members of a grieving suburban family. The film's raw, honest discussions of mental health and the complexities of grief made it a massive critical and commercial success. Redford became the first actor to win an Academy Award for Best Director for their debut film, and the movie also won Oscars for Best Picture, Best Adapted Screenplay, and Best Supporting Actor for Hutton. —Wesley Stenzel

09 of 20

The Natural (1984)

Widely regarded as one of the best baseball movies ever, The Natural adapts Bernard Malamud's 1952 novel of the same name. Redford stars as naturally talented baseball player, Roy Hobbs, who endures a series of trials and tribulations as he fights for the title of "the best there ever was." It's a parable of American exceptionalism and the King Arthur myth reimagined through sport. Hobbs and his struggles with romance, career success, and temptation seem the perfect vehicle for Redford, his All-American good looks ideal for this All-American tale of the nation's favorite pastime. He immersed himself in the sport, modeling his swing off real baseball star Ted Williams. It marked a career resurgence for Redford as his first acting role in three years, and though many have called the Barry Levinson film overly sentimental, it's a quintessential "guy cry" movie. —Maureen Lee Lenker

10 of 20

Out of Africa (1985)

Out of Africa is Redford and Pollack's sixth and probably most successful collaboration. Based on memoirs of Dutch Baroness Karen von Blixen, the film stars Meryl Streep as the married writer who gets involved in a long, complicated romantic saga with Englishman Denys Finch Hatton (Redford). The film received mixed reviews, many criticizing Redford for omitting an English accent completely. But the Academy has never really catered to the public and nominated the 1986 drama for 11 Academy Awards, taking home seven wins, including Best Picture, Best Director, and Best Adapted Screenplay. — Yolanda Machado

11 of 20

A River Runs Through It (1992)

After comparisons of an up-and-coming Brad Pitt to a young Redford, the elder actor cast the heartthrob in his third directorial turn, 1992's A River Runs Through It. The actors never share the screen in the ode to fly fishing and brotherly love, but Redford does serve as an uncredited narrator, speaking as the future version of Pitt's onscreen brother played by Craig Sheffer. —Jillian Sederholm

12 of 20

Sneakers (1992)

Redford led an impressive ensemble that also included Dan Aykroyd, Sidney Poitier, River Phoenix, David Strathairn, and Ben Kingsley in this snappy heist thriller. Redford's calm, collected charm makes him an ideal fit to play a reformed thief — he's remarkably similar to his characters from both The Sting and The Old Man & the Gun here, once again pulling off daring heists with a twinkle in his eye and a subtle sense of care and compassion for his crew. —Wesley Stenzel

13 of 20

Indecent Proposal (1993)

In Adrian Lyne's 1993 sexy revenge thriller Indecent Proposal, Redford plays a suave billionaire gambler who tears apart the lives of a cash-strapped young couple, played by Demi Moore and Woody Harrelson, when he makes a $1 million offer to spend a single night with the wife, who ultimately accepts and falls for him. Although the film received mostly negative reviews from critics, it was a box office smash, becoming one of the highest grossing films of that year. —Jillian Sederholm

14 of 20

Quiz Show (1994)

Quiz Show, Ralph Fiennes, ... — 'Quiz Show'. Miramax/Everett

This fact-based directorial effort from Redford examines class and celebrity through the prism of the Twenty-One quiz show scandals during the 1950s, and earned him a second Best Director nomination at the Oscars. Ralph Fiennes stars as Charles Van Doren, a charming player for whom the game show was rigged. Redford directs a wonderful cast to endlessly nuanced performances, creating tense scenarios where we simultaneously pity the players and want them to get caught. —Wesley Stenzel

15 of 20

Up Close and Personal (1996)

Michelle Pfeiffer and Redford's romance drama Up Close and Personal would be dead on arrival if it premiered today. Pfeiffer stars as Tally Atwater, a young up-and-coming journalist who works for Redford's Warren Justice. The two embark on a complicated mentor-like relationship where they (take a wild guess…) end up falling in love, despite the over two decade age gap between the stars (oh, and Warren is Tally's boss!). —Yolanda Machado

16 of 20

All Is Lost (2013)

Redford was snubbed by the Oscars for his leading role in J.C. Chandor's deeply haunting — and remarkably thrilling —All Is Lost, a one-man show about a sailor stranded at sea in a massive storm. Redford might not share screen time with any people in the film, but we can definitely think of worse ways to spend our time than sailing out on the ocean aboard a lonely boat, with only legendary Hollywood acting chops to keep us company. —Joey Nolfi

17 of 20

Captain America: The Winter Soldier (2014)

Redford played Alexander Pierce, a mysterious S.H.I.E.L.D. official, in this 2014 MCU sequel. The actor's presence offers a tangible connection to the '70s conspiracy thrillers like Three Days of the Condor and All the President's Men that inspired its tone. Pierce's murky political agenda and character motivations allow Redford to embrace his dark side, demonstrating the actor's fearlessness when it comes to challenging his usual persona. He briefly reprised the role for a cameo in 2019's Avengers: Endgame. —Wesley Stenzel

18 of 20

A Walk in the Woods (2015)

Based on Bill Bryson's hiking autobiography, A Walk in the Woods stars Redford as Bryson as he returns home from England after two decades with the intent to retire and live a quiet life with his wife (Emma Thompson) in New Hampshire — until he suddenly decides to hike the 2,000 mile Appalachian trail. When his wife insists he not go alone, he is joined by a long-lost buddy, Stephen Katz (Nick Nolte). Together, they venture on a journey that has them not only seeing the beautiful sights, but reflecting on their own issues that have kept the two friends apart for nearly 40 years. —Yolanda Machado

19 of 20

Our Souls at Night (2017)

Electric chemistry abounds in the 2017 slow-burning romance Our Souls at Night, which unites classic Hollywood titans Jane Fonda and Redford in a subtly simmering love story about a widow and widower who connect after years of living side by side. Thankfully, the material at hand is inherently juicy, but its leads tap into a kind of deep, mystic energy accessible only by two bright stars from a bygone era finding each other on our screens at just the right time in their respective careers. —Joey Nolfi

20 of 20

The Old Man & the Gun (2018)

038_TOMATG_00757 — 'The Old Man & the Gun'. Eric Zachanowich/Fox

Redford's final leading performance came in this light drama about a gentleman bank robber in the twilight years of his career. The actor's work here is a fitting conclusion to a legendary career, softly highlighting all the strengths that made him a generation-defining movie star. He has warm chemistry with co-stars Sissy Spacek, Danny Glover, and Tom Waits, imbuing each conversation with gentle confidence and quiet kindness. —Wesley Stenzel

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