The late great actor Robert Redford has pᴀssed away aged 89, but he leaves behind a legacy of outstanding and influential performances. As an acclaimed actor, director, producer, and founder of the Sundance Film Festival, Redford’s career traverses the length and breadth of modern Hollywood, as he has contributed significantly to the art form that is cinema.

While Redford’s work as a director includes acclaimed releases like the Best Picture winner Ordinary People, it’s his work as an actor for which he’s best known. With a suave and charismatic persona, Redford was one of the most beloved leading men of the 20th century, and his performances across comedy, drama, thrillers, and Westerns speak for themselves.

Bill McKay In The Candidate (1972)

Robert Redford set his sights on the absurdity of American political campaigns in the clever and funny political satire The Candidate. With an Oscar-winning screenplay from the speechwriter Jeremy Larner, the film had an extra layer of authenticity, considering he wrote for Senator Eugene J. McCarthy during his 1968 Democratic presidential nomination.

With intense charisma and leading man appeal, Redford’s striking good looks echoed those of genuine presidential candidates like JFK, highlighting how presidential campaigns extended to issues well beyond the candidate’s political beliefs. In a political landscape where personality is now more important than ever, Redford’s role as Bill McKay has only become more relevant in the decades since.

Paul Bratter In Barefoot In The Park (1967)

Robert Redford’s breakout success as a leading man came when he played Paul Bratter in Barefoot in the Park opposite his frequent co-star Jane Fonda. As a rom-com exploring a newly married couple’s relationship troubles, things take a turn for the worse when they rent a rundown New York apartment and come face-to-face with their eccentric neighbors.

While it’s always a treat to see Redford and Fonda sharing the screen, Redford proved he was more than just a pretty face and could truly excel in comedies with Barefoot in the Park. As the movie that opened the door for Redford’s bright future as a Hollywood star, this was an essential release in his impressive career.

Roy Hobbs In The Natural (1984)

With all-American charm and rugged maturity, Robert Redford was the perfect choice to star as Roy Hobbs in the sports drama The Natural. As a compelling adaptation of the 1952 novel by Bernard Malamud, the movie tracked Hobbs’ career as an innately talented baseball star across the decades.

Redford captured the hope, desperation, and redemption of Hobbs’ baseball career and the almost mythical way this older sports star comes out of nowhere with practically supernatural talents. While Redford’s performance was the beating heart of The Natural, it was elevated by great turns from co-stars like Robert Duvall and Glenn Close.

Alexander Pierce In Captain America: The Winter Soldier (2014)

While Robert Redford’s career slowed down in the 2010s before his eventual retirement in 2018, he remained at the forefront of mainstream popular culture when he joined the MCU in Captain America: The Winter Soldier. As the head of S.H.I.E.L.D. and leader of the Hydra cell operating the Triskelion, Redford played Alexander Pierce.

Although Redford’s persona lent itself well to heroic and idealistic roles, the twist reveal of Alexander’s villainy toward the end of the film was a delightful change of pace. Redford’s appearance in The Winter Soldier felt like it bridged the gap between classic Hollywood and modern blockbusters, as a new generation of viewers was introduced to his star power.

Our Man In All Is Lost (2013)

It’s a testament to Robert Redford’s enduring talent that, in his late 70s, he delivered one of his very best performances as the only cast member in a movie with just 51 spoken English words. This was the survival drama All Is Lost, where Redford portrayed a man struggling to survive while lost at sea.

This was the type of physically demanding performance that would have been difficult for an actor of any age, yet Redford delivered a tour de force performance that was enthralling from start to finish. All Is Lost stands as a late-career triumph from Redford that rightfully should have been nominated for an Oscar.

Joseph Turner In Three Days Of The Condor (1975)

Three Days of the Condor captured the paranoia of a post-Watergate society perfectly as Robert Redford played the CIA analyst Joseph Turner, who is embroiled in a conspiracy of murder. As a bookish agent who analyzes literature for intelligence purposes, Turner is thrust far beyond his comfort zone when he finds his colleagues ᴅᴇᴀᴅ and realizes he might be next.

As a tense thriller that felt totally believable considering the atmosphere of distrust around this period, Three Days of the Condor allowed Redford to show off his ability to balance vulnerability with resourcefulness. With Turner as an everyman hero forced into survival mode, this Sydney Pollack classic was truly one of his best.

Jeremiah Johnson In Jeremiah Johnson (1972)

Robert Redford gave an outstanding performance as the legendary mountain man Jeremiah Johnson in this Sydney Pollack classic. As a transformative turn that traded Redford’s regular clean-shaven persona to portray a hardened, self-reliant man supporting himself as a trapper in the Rocky Mountains, this was just one of many examples of the actor testing his dramatic skills.

While younger viewers might recognize the popular internet meme of Jeremiah nodding his head, there was far more to this film’s appeal than just its online resurgence. With Jeremiah Johnson, Redford delivered a performance that captured the gravitas and terror of the American West like few films before it, and it stands as a career highlight.

Johnny Hooker In The Sting (1973)

The Sting was a major hit with audiences and critics alike and went on to win an impressive seven Academy Awards, including Best Picture and Best Director. With Robert Redford as the charming and clever con artist Johnny Hooker, this was the perfect showcase of the actor’s intense charisma and ability to balance wit with huge dramatic stakes.

As the story of two grifters trying to pull off the ultimate con, the old-fashioned feeling of The Sting, paired with the ragtime music of Scott Joplin, gave this caper classic a timeless aura. Everything about The Sting just worked, as seeing Redford share the screen once again with his Butch Cᴀssidy co-star Paul Newman was the cherry on top.

Bob Woodward In All The President’s Men (1976)

Many of Robert Redford’s greatest roles in the 1970s leaned into the cultural effects of the Watergate scandal, but it was All the President’s Men that actually told the story of this world-changing scandal. With Redford as investigative journalist Bob Woodward and Dustin Hoffman playing his colleague Carl Bernstein, this political thriller explored how good reporting brought down President Nixon.

All the President’s Men remains a landmark portrayal of investigative journalism, with Redford and Hoffman capturing the focus and perseverance needed to uncover the truth. Though its real-life circumstance may appear milder when compared to today’s climate of surveillance and misinformation, the film’s story underscores the enduring importance of challenging corruption and pushing back against fake news.

The Sundance Kid In Butch Cᴀssidy And The Sundance Kid (1969)

There was only going to be one answer when it came to Robert Redford’s greatest performance, as his role in Butch Cᴀssidy and the Sundance Kid marked a turning point for the entire film industry. As the beginning of the New Hollywood movement, a line can be drawn between this performance and modern cinema.

With Robert Redford as the Sundance Kid and Paul Newman as Butch Cᴀssidy, this landmark Western boasted innovative techniques, including freeze-frames, montages, and contemporary music. Butch Cᴀssidy and the Sundance Kid helped usher in a modern cinematic era, with Robert Redford’s performance influencing directors like Scorsese and Spielberg while paving the way for more naturalistic acting styles.