Honoring Robert Redford: 20 Defining Movies of a Legend

Honoring Robert Redford: 20 Defining Movies of a Legend

Robert Redford stands as one of Hollywood’s most beloved actors and directors, captivating audiences for over five decades. His golden hair, piercing blue eyes, and natural charm made him a heartthrob, but his talent kept him relevant long after his matinee idol days. From romantic comedies to political thrillers, Redford chose roles that showcased both his acting range and his commitment to meaningful storytelling. His career represents the perfect blend of commercial success and artistic integrity.

1. Butch Cassidy and the Sundance Kid (1969)

Paul Newman and Robert Redford created movie magic in this Western that changed everything. Their chemistry as outlaws on the run felt so natural that audiences forgot they were watching actors.

The film mixed humor with action in ways nobody expected from a cowboy movie. Redford’s Sundance Kid was cool, confident, and just dangerous enough to be exciting.

This movie launched Redford into superstardom and proved he could hold his own against Newman, one of Hollywood’s biggest names. The bicycle scene and Bolivia adventure became legendary moments that people still quote today.

2. The Sting (1973)

Redford reunited with Paul Newman for this clever con artist caper that fooled everyone, including the audience. Playing Johnny Hooker, Redford showed he could be both charming and sneaky.

The movie’s twist ending surprised viewers who thought they knew what was happening. Redford’s character seemed like a small-time crook, but he was actually part of something much bigger.

This film won seven Academy Awards and proved that Redford and Newman together were box office gold. The ragtime music and 1930s setting created a perfect backdrop for their elaborate scheme against a dangerous mob boss.

3. The Way We Were (1973)

Barbra Streisand and Robert Redford created one of cinema’s most heartbreaking love stories. Their characters seemed wrong for each other, yet their romance felt completely real and devastating.

Redford played Hubbell, a golden boy writer who couldn’t match his girlfriend’s political passion. His performance showed how sometimes love isn’t enough when people want different things from life.

The movie made audiences cry and think about their own relationships. Redford’s ability to show vulnerability beneath his confident exterior made Hubbell both frustrating and sympathetic, creating a character that stayed with viewers long after leaving the theater.

4. All the President’s Men (1976)

He brought real journalism to the big screen as Washington Post reporter Bob Woodward. His investigation into the Watergate scandal showed how patient detective work could bring down a president.

Working alongside Dustin Hoffman’s Carl Bernstein, Redford made newspaper reporting look exciting and important. The movie proved that smart dialogue and careful research could be just as thrilling as car chases.

This film earned Redford respect as a serious actor who cared about important stories. His portrayal of Woodward was so convincing that people forgot they were watching a movie about recent history that had changed America forever.

5. The Natural (1984)

A story of redemption and resilience lies at the heart of The Natural. The film follows a gifted baseball player whose career is derailed but later rekindled by a second chance at glory. Its timeless themes of hope and perseverance resonate far beyond sports.

Redford’s portrayal captures both the vulnerability of a man haunted by mistakes and the determination to reclaim greatness. The film’s iconic imagery, from the bat “Wonderboy” to the fireworks-filled final home run, cemented it as a classic.

Audiences connected with the blend of myth, Americana, and sheer emotional pull. It showcased Redford’s ability to embody ordinary men carrying extraordinary burdens. The role remains one of the most beloved in his long career.

6. Out of Africa (1985)

Set against the vast backdrop of Kenya, it tells a tale of love, loss, and cultural divide. Redford’s chemistry with Meryl Streep anchors the film, giving weight to its romance.

The film earned critical acclaim, winning seven Academy Awards including Best Picture. Its breathtaking cinematography paired with heartfelt performances made it unforgettable.

Redford’s character embodied charm, freedom, and the complexity of fleeting relationships. The role deepened his reputation as a romantic lead in Hollywood’s golden epics. It remains a cornerstone of his filmography, blending grandeur with humanity.

7. Three Days of the Condor (1975)

Suspense and paranoia fuel Three Days of the Condor, a tense Cold War-era thriller. Redford plays a low-level CIA analyst who finds himself hunted after his entire office is assassinated. The film captures the era’s growing distrust of government institutions.

His performance balances vulnerability with sharp intellect, transforming an ordinary man into a reluctant survivor. The chemistry with Faye Dunaway adds unexpected intimacy amid the danger. Themes of secrecy, betrayal, and moral ambiguity run throughout the story.

It remains a landmark political thriller, still resonant decades later. Redford’s work here cemented his reputation as both a thinking man’s action star and a cultural voice of the 1970s.

8. Jeremiah Johnson (1972)

Set in the Rocky Mountains, it follows a man who abandons society to live as a hermit and trapper. Redford embodies resilience, resourcefulness, and the quiet dignity of frontier life. The film highlights both the beauty and brutality of the wilderness.

Its sweeping landscapes mirror the character’s internal solitude and struggles. With minimal dialogue, Redford conveys depth through physicality and presence.

The movie helped redefine the Western genre for a modern audience. It remains one of his most iconic and haunting performances.

9. The Great Gatsby (1974)

Redford portrays Jay Gatsby, the enigmatic millionaire driven by longing for lost love. His performance balances charm, melancholy, and obsession.

The film captures the excess and emptiness of the Jazz Age. Costumes and sets reflected the novel’s grandeur, while Redford gave Gatsby humanity beneath the myth.

Though reception was mixed, his portrayal remains unforgettable. Themes of desire and disillusionment are timeless. This role further established him as a leading man capable of embodying American archetypes.

10. Ordinary People (1980) – Director

Subtle yet devastating, Ordinary People showcased Redford’s mastery as a director. The story examines grief and fractured family bonds with raw honesty.

His careful guidance brought out extraordinary performances, particularly from Mary Tyler Moore and Timothy Hutton. The film captured the pain of unspoken emotions and the difficulty of healing. It won four Academy Awards, including Best Picture and Best Director.

Redford proved he could command artistry behind the camera with as much presence as on screen. The film resonated deeply with audiences for its universality and truth. It remains one of the most acclaimed directorial debuts in cinema history.

11. The Candidate (1972)

His character wrestles with integrity versus ambition, reflecting timeless political dilemmas. The film critiques media manipulation and campaign cynicism.

Redford’s performance is sharp, witty, and disarmingly human. The famous closing line, “What do we do now?” still lingers as one of the great endings in political cinema.

It captured the uncertainty of public service in an age of disillusionment. The film remains a benchmark for political dramas.

12. Downhill Racer (1969)

Redford plays an arrogant skier striving for Olympic glory, alienating those around him in pursuit of victory. The film explores the cost of obsession and single-minded drive. Sparse dialogue allows his intensity to speak louder than words.

Realistic skiing sequences brought grit and authenticity to the story. Redford captures both the thrill of speed and the loneliness of selfish ambition.

The movie broke new ground for sports films, focusing more on psychology than spectacle. It solidified his reputation as an actor unafraid of complex, flawed roles.

13. A River Runs Through It (1992) – Director

Based on Norman Maclean’s novella, it explores family bonds, spirituality, and the passage of time. Redford’s direction infused the story with reverence for nature and tradition.

The fly-fishing sequences became metaphors for life’s fleeting beauty. Brad Pitt’s breakout performance under his guidance marked a generational shift in Hollywood.

Themes of loss and legacy run through every frame. Redford narrated the film with quiet poignancy, tying past and present together. It remains one of his most poetic contributions to cinema.

14. Barefoot in the Park (1967)

Newlyweds Paul and Corie Bratter learned that love doesn’t automatically solve all problems. Redford’s early performance showed his natural comedy timing alongside Jane Fonda’s energetic character who wanted to try everything.

The film captured the excitement and challenges of young marriage in 1960s New York. His conservative lawyer character clashed with his wife’s free-spirited approach to life and adventure.

Redford’s charm made Paul likeable even when he was being stuffy and overly cautious. The movie’s apartment setting and generational conflicts created a time capsule of changing American values, while their relationship showed how opposites can attract but also drive each other crazy.

15. The Electric Horseman (1979)

Rodeo champion Sonny Steele stole a prize horse to save it from corporate exploitation. Redford’s character represented authentic Western values fighting against modern commercialization and artificial entertainment.

The film paired him with Jane Fonda as a reporter who initially wanted a story but ended up understanding his mission. Their chemistry developed naturally as they traveled through beautiful Western landscapes.

Redford’s performance balanced humor with genuine concern for the horse’s welfare. The movie criticized how corporations turn everything into products, while his character’s journey back to his roots showed that some things are more important than money or fame.

16. Indecent Proposal (1993)

Billionaire John Gage offered a million dollars for one night with another man’s wife, creating an impossible moral dilemma. Redford’s sophisticated character seemed charming and reasonable, which made his proposal even more disturbing.

The film explored how money can complicate love and marriage in unexpected ways. His performance walked a fine line between seductive and predatory, keeping audiences unsure about his true motivations.

Redford’s natural elegance made Gage’s offer seem almost reasonable, which was exactly what made the character so dangerous. The movie asked difficult questions about love, money, and temptation that audiences debated long after leaving the theater, proving that some moral questions have no easy answers.

17. The Great Waldo Pepper (1975)

Waldo Pepper lived for the thrill of flying and the dream of aerial combat he missed during World War One. Redford’s character represented a generation of men who felt they had missed their chance for glory.

The film captured the dangerous excitement of early aviation when pilots performed stunts for crowds at county fairs. His character’s obsession with proving himself led to increasingly risky behavior.

Redford’s performance showed how some people need danger to feel alive. The spectacular flying sequences and period details created an authentic look at America’s fascination with aviation heroes, while his character’s journey explored themes of missed opportunities and second chances.

18. The Horse Whisperer (1998)

Redford both directed and starred in this story about recovery, patience, and understanding.

The film explored how tragedy affects both humans and animals in similar ways. His character’s gentle methods contrasted with traditional horse training, showing that healing takes time and trust.

Redford’s performance emphasized quiet strength and wisdom earned through years of experience with horses and people. The Montana ranch setting and beautiful cinematography created a peaceful world where healing seemed possible, while his relationship with the injured horse became a metaphor for overcoming trauma.

19. All Is Lost (2013)

A sailor fought for survival alone on the ocean with almost no dialogue to carry the story. Redford’s nearly wordless performance proved that great acting doesn’t always require great speeches or dramatic scenes with other actors.

The film stripped away everything except one man’s determination to live. His character faced each new crisis with practical problem-solving and quiet courage that never felt showy or artificial.

At age 77, Redford delivered one of his most physically demanding and emotionally honest performances. The movie’s simple story and his committed acting created a powerful meditation on human resilience, showing that survival sometimes depends on refusing to give up even when everything seems hopeless.

20. The Old Man & The Gun (2018)

Redford portrays a real-life gentleman bank robber who lives by charm and principle. The role carried echoes of his earlier characters—rebels, dreamers, and rogues.

His performance balances nostalgia with vitality, offering a graceful farewell. Critics praised the film as a perfect capstone to his career.

It radiates warmth, wit, and understated charisma. The story celebrates a man who lived life on his own terms. As a swan song, it felt both fitting and unforgettable.