25 Best Robert Redford Movies of All Time

The Sting

Five years ago, Robert Redford walked off the screen. After 2018’s The Old Man and the Gun, the actor closed the book on a career that stretched across six decades across multiple genres. Redford leaves behind a remarkable legacy, with major contributions to everything from New Hollywood films of the '70s to the indie revival of the '90s to the superhero explosion of the 2010s. He’s served as star, director, producer, and founder of the Sundance Film Festival, contributing to great films in front of and behind the camera.

Unsurprisingly, Redford leaves behind a massive filmography filled with fantastic films. That can be a bit overwhelming to those who want to revisit his golden age or see what all the fuss is about. This list narrows down the 25 best Robert Redford movies, celebrating his work as a lead, a supporting actor, and as a director.

1 – War Hunt (1962)

War Hunt
Image Credit: United Artists.

Although Redford had already impressed audiences with his stage appearances, and even had an uncredited appearance as a basketball player in Tall Story from 1960, his proper film debut came in War Hunt in 1962. A morally complex story about the end of the Korean War, War Hunt stars John Saxon as the secretive Private Endore, whose odd behavior helps the Americans but also threatens the Armistice. Redford’s idealistic Private Loomis must weigh the cost of reporting Endore or letting him continue his dubious activities.

2 – Inside Daisy Clover (1965)

Inside Daisy Clover
Image Credit: Warner Bros.

War Hunt received acclaim from audiences and critics. But the Robert Mulligan-directed Inside Daisy Clover made Robert Redford a name to remember, thanks to his Golden Globe-winning performance as a bisexual man who marries the titular character, played by Natalie Wood. Inside Daisy Clover flopped at the box office at the time and was drubbed by critics, but it has since grown to become a respected, if uneven, part of mid-60s cinema.

3 – This Property is Condemned (1966)

This Property is Condemned
Image Credit: Paramount Pictures.

A year after Inside Daisy Clover, Redford reteamed with Natalie Wood for this Tennessee Williams adaptation. As a railroad executive who falls for Wood’s wild teen, Redford shows early signs of the easy charm he’ll develop as his primary trait. But This Property is Condemned is tempered by his role as an utterly unlikable character who comes to destroy a small town for the sake of his bosses. At once alluring and repellent, Redford steals every scene he’s in.

4 – Barefoot in the Park (1967)

Barefoot in the Park
Image Credit: Paramount Pictures.

Redford’s early work certainly had its love plots, but he didn't become a romantic lead until Neil Simon’s Barefoot in the Park. As a conservative lawyer who marries a free-spirited woman played by Jane Fonda, Redford gets to play the fuddy-duddy and foil. But even when he’s a stick-in-the-mud, Redford has enough charisma to make viewers side with him. This ability to attract and frustrate viewers will serve Redford well during his heyday in the 1970s.

5 – Butch Cassidy and the Sundance Kid (1969)

Butch Cassidy and the Sundance Kid
Image Credit: 20th Century Studios.

It’s impossible to overstate the importance of Butch Cassidy and the Sundance Kid, and not just for Redford’s career. Not only did the movie establish him as a bonafide movie star of the budding New Hollywood movement, alongside co-star Paul Newman, but it also provided a unique revision of the Western genre. The friendly banter between the two leads sets the mold for buddy movies for years to follow, all while giving audiences a unique take on the old west. Even today, filmmakers still try to copy the easy allure that Redford and Newman bring to Butch and Sundance.

6 – The Hot Rock (1972)

The Hot Rock
Image Credit: 20th Century Studios.

While he’s played more than a few criminals over the years, the strikingly handsome Redford seems an unlikely choice for a gritty crime movie. And yet, he’s one of the best parts of the Richard Westlake adaptation The Hot Rock, directed by Peter Yates and written by William Goldman. As Westlake’s ne’er do well hero John Dortmunder, Redford has a nasty streak rarely found in his films, even as he perfectly embodies the character’s genius for cons and heists.

7 – Jeremiah Johnson (1972)

Jeremiah Johnson
Image Credit: Warner Bros.

These days, young people know Jeremiah Johnson for a short video of a bearded, burly Redford nodding with approval. They may not realize that Jeremiah Johnson is a captivating portrait of the titular mountain man. Against the revisionist edge of his Sundance Kid, Redford grounds Johnson with a world-weariness that reflects his character’s disgust with modern society. The movie’s treatment of Native peoples doesn’t hold up, but there’s no denying the power of Redford’s quiet performance.

8 – The Candidate (1972)

The Candidate
Image Credit: Warner Bros.

Where Jeremiah Johnson played its traditional frontier story relatively straight, Redford induldged his counter-culture instincts for the satire The Candidate. The Academy-Award-winning screenplay by Jeremy Larner tells the story of a desperate political specialist (Peter Boyle) who enlists the idealistic young Bill McKay (Redford) to run an unwinnable campaign against a powerful Republican opponent. Redford’s natural good looks and likability make him a believable underdog politician but former speech writer Larner undercuts what could be a feel-good story with a cynical edge.

9 – The Sting (1973)

The Sting
Image Credit: Universal Pictures.

Butch Cassidy and the Sundance Kid was a huge hit, making over $100 million in ticket sales and earning seven Oscar nominations. But when Redford rejoined with Newman and director George Roy Hill for The Sting, they experienced even greater success, scoring over $150 million at the box office and netting ten Oscar nominations, including Redford’s only Best Actor nod. With an irresistible heist plot and Redford and Newman at their best, it's no surprise that The Sting won over fans and critics alike.

10 – The Way We Were (1973)

The Way We Were
Image Credit: Columbia Pictures.

For such a famously handsome actor, Redford did few openly romantic movies during his prime. Perhaps the closest he came to playing a romantic lead occurred in The Way We Were, opposite Barbara Streisand. As an apolitical writer entering Hollywood, Redford improves upon his Barefoot in the Park character, especially with Streisand’s performance as a political activist. Today, the main song has more prestige than the movie, but The Way We Were deserves a second look from Redford fans.

11 – The Great Waldo Pepper (1975)

The Great Waldo Pepper
Image Credit: Universal Pictures.

Although Newman didn’t join Redford for a third collaboration with George Roy Hill, The Great Waldo Pepper still stands alongside Butch Cassidy and The Sting as some of the actor’s best work. Unlike the rapscallion he played in his previous collaborations with Hill, Redford’s Waldo Pepper has a chip on his shoulder, feeling despair for missing out on World War I. The pilot’s attempts to recover lost glory cast a caustic look at post-war America.

12 – Three Days of the Condor (1975)

Three Days of the Condor
Image Credit: Paramount Pictures.

In the mid-1970s, the counter-culture spirit of the '60s turned into outright hostility against institutions, which filtered into Hollywood. Redford got in on the action with one of the decade’s best paranoid thrillers, Three Days of the Condor. As a CIA analyst forced on the run after barely escaping the destruction of his unit, Redford puts his disarming charisma to the test, forced to rely on strangers such as Faye Dunaway’s passerby to thwart the government officials looking for him.

13 – All the President’s Men (1976)

All the President’s Men
Image Credit: Warner Bros.

Many of Redford’s movies turned a skeptical eye towards mainstream politics, none as effectively as 1976’s All the President’s Men. As Washington Post investigative reporter Bob Woodward, alongside Dustin Hoffman as Carl Bernstein, Redford portrays a key figure in a scandal that rocked the nation. Even though none of the movie’s four Academy Award wins went to Redford, All the President’s Men would have never happened without his work in front of or behind the camera.

14 – A Bridge Too Far (1977)

A Bridge Too Far
Image Credit: United Artists.

Redford got his first big role in the movie War Hunt, but he didn’t return to the genre until the Richard Attenborough-directed A Bridge Too Far in 1977. An epic retelling of a failed Allied operation in the Netherlands, A Bridge Too Far boasts a script by William Goldman and an all-star ensemble cast, which includes James Caan, Sean Connery, and Michael Caine. Redford plays a relatively small part as Major Julian Cook, but he’s memorable as an American officer who clashes with his English counterparts.

15 – Brubaker (1980)

Brubaker
Image Credit: 20th Century Studios.

Brubaker begins with Redford on familiar ground, playing a convict behind bars. But when the convict is revealed to be new Arkansas state prison warden Henry Brubaker, we realize that he’s combining his conman-type character with the social crusaders he’s played elsewhere. The story of an activist warden trying to reform a corrupt prison system, Brubaker puts Redford with some other great actors of the era, including Yaphet Kotto, Morgan Freeman, and M. Emmet Walsh.

16 – Ordinary People (1980)

Ordinary People
Image Credit: Paramount Pictures.

Ordinary People stars Donald Sutherland, Mary Tyler Moore, and Elizabeth McGovern as the troubled Jarrett family. Robert Redford never appears in the film, which might make you wonder why it’s on this list. The answer is simple: Redford made his directorial debut with Ordinary People, which earned him his first Academy Award. A sad but deeply humane film, Ordinary People showcases Redford’s sensitivity as a filmmaker, which will be a defining part of his approach as a director.

17 – The Natural (1984)

The Natural
Image Credit: Tri-Star Pictures.

In the 1980s, America moved past the cynicism of the '70s and embraced a more optimistic outlook, which was reflected in Redford’s work. Nowhere is that more apparent than in Barry Levinson’s adaptation of the Bernard Malamud novel The Natural. Screenwriters Roger Towne and Phil Dusenberry make major changes to the novel's tone, but that gives Redford more room to work as a talented pitcher whose career never reaches the heights he expected.

18 – Out of Africa (1985)

Out of Africa
Image Credit: Universal Pictures.

With a quarter-century’s worth of film credits to his name, Robert Redford was already a favorite in 1985. But Out of Africa cemented his reputation as a Hollywood legend. Directed by Sydney Pollack and written by Kurt Luedtke, Out of Africa starred Redford and Merryl Streep as big-game hunter Denys Finch Hatton and Danish Baroness Karen Blixen, who fall in love in Kenya. None of the movie’s 10 Academy Award nominations nor its seven wins went to Redford, but his participation helped the movie’s reputation.

19 – Legal Eagles (1986)

Legal Eagles
Image Credit: Universal Pictures.

It’s a bit of a surprise that Redford followed the Tony and Oscar winner Out of Africa with the comedy thriller Legal Eagles, but that just shows the actor’s underrated range. Alongside Debra Winger and Darryl Hannah, Redford stars as an assistant district attorney who gets caught up in a dispute between a performance artist and a powerful millionaire over ownership of a valuable painting. This screwball caper does get burdened by an overstuffed plot, but Redford keeps things as breezy as possible.

20 – Sneakers (1992)

Sneakers
Image Credit: Universal Pictures.

With the 60s well behind him, Redford no longer carried the same subversive reputation he once had. But he still had that rebellious streak, which was put to good use in the thriller Sneakers. As former activist Martin Bishop, Redford leads a team of thieves and hackers who get roped into a dangerous mission by a figure from his past. Redford’s chemistry with co-stars Sydney Pointier, Mary McDonnell, and Dan Ackroyd shines, even as director Phil Alden Robinson ratchets up the tension.

21 – Indecent Proposal (1993)

Indecent Proposal
Image Credit: Paramount Pictures.

It may have been one of the biggest hits of its year, but Indecent Proposal scandalized filmgoers of the early 90s. Provocative director Adrian Lyne casts Redford as a devilish millionaire who tempts a struggling couple, played by Demi Moore and Woody Harrelson, with an offer they cannot refuse. Screenwriter Amy Holden Jones keeps the sympathy clearly with the couple and against the rich man, but Redford’s natural appeal makes it hard to completely hate him.

22 – All is Lost (2013)

All is Lost
Image Credit: Lionsgate Films.

As the founder of the Sundance Film Festival, Redford has always respected and supported independent cinema. So it makes sense that he would sign up for the ambitious project All is Lost, from director J.C. Chandor. Redford plays the only character in the movie, a sailor credited as “our man” who must marshal all of his courage to survive after getting lost at sea. With barely more than 50 words spoken in the movie, Redford gives a remarkably layered physical performance, one of the purest examples of his skills as an actor.

23 – Captain America: The Winter Soldier (2014)

Captain America The Winter Soldier
Image Credit: Walt Disney Studios Motion Pictures & Marvel Studios.

For some readers, the inclusion of a Marvel superhero movie on this list might seem like an insult to Redford’s career. After all, superhero movies are the exact opposite of the indie movies he champions. But there’s no denying the sheer chemistry the 77-year-old actor brought to Captain America: The Winter Soldier as corrupt politician Alexander Pierce. In a movie that included super-assassins and laser-welding flying aircraft characters, Redford’s smile remains the movie’s greatest effect.

24 – Pete’s Dragon (2016)

Pete’s Dragon
Image Credit: Walt Disney Studios Motion Pictures.

Redford starred in a few breezy, colorful films in his day, but he never seemed like a good fit for Disney movies. But director David Lowery reimagines the minor Disney musical Pete’s Dragon as a grounded fairytale starring Bryce Dallas Howard as a forest ranger who finds a young boy (Oakes Fegley) who has befriended a giant green dragon. Redford adds gravitas as the father of Howard’s character, whose sense of wonder is restored when he recalls his relationship with the dragon.

25 – The Old Man and the Gun (2018)

The Old Man and the Gun
Image Credit: Searchlight Pictures.

As this list shows, Redford played many different types of characters over his career. But he’s never better than when he’s a charming criminal. So it’s fitting that his final film The Old Man and the Gun gives him one last chance to break out the old wink and smile as an escaped bank robber who falls for a local woman (Sissy Spacek) while on the run. Reteaming with David Lowery and starring alongside Donald Glover and Tom Waits, Redford gets to go out on his own terms in a delightful performance that captures everything great about the legendary actor.

Author: Joe George

Title: Pop Culture Writer

Expertise: Film, Television, Comic Books, Marvel, Star Trek, DC

Bio:

Joe George is a pop culture writer whose work has appeared at Den of Geek, The Progressive Magazine, Think Christian, Sojourners, Men's Health, and elsewhere. His book The Superpowers and the Glory: A Viewer's Guide to the Theology of Superhero Movies was published by Cascade Books in 2023. He is a member of the North Carolina Film Critic's Association.