Robert Redford’s Career: From ‘War Hunt’ to ‘Omniboat: A Fast Boat Fantasia’

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Robert Redford is a true Hollywood icon, an actor who defined the American leading man for decades. With his classic good looks, natural charm, and understated intensity, he created a string of memorable characters that have stood the test of time. Redford’s career is marked by his ability to play both romantic heroes and complex, morally ambiguous figures. He often chose roles that reflected his own interests, particularly in politics and the environment, using his stardom to tell important stories.

Beyond his work in front of the camera, Redford made a huge impact on the film industry as a director and as the founder of the Sundance Institute. This dedication to independent filmmaking helped launch the careers of countless writers and directors. But it was his on-screen presence that first made him a star. From his early days as a promising young actor to his later roles as a respected veteran, Redford’s performances have consistently captivated audiences, cementing his status as a legendary figure in cinema.

‘War Hunt’ (1962)

'War Hunt' (1962)
T-D Enterprises

This film marked Robert Redford’s screen debut. Set during the final days of the Korean War, the story centers on a young, psychopathic soldier named Private Endore who enjoys killing. Redford plays Private Roy Loomis, a new recruit who arrives at the front and is disturbed by Endore’s behavior. Loomis is the moral compass of the film, representing the decency and sanity that is lost in the chaos of war.

As his first role, it gave audiences a glimpse of the thoughtful and serious actor Redford would become. His character, Loomis, tries to understand the strange and silent Endore, but ultimately stands against his brutal actions. The low-budget film was a gritty and realistic look at the psychological toll of combat, and Redford’s performance stood out, signaling the arrival of a major new talent in Hollywood.

‘Inside Daisy Clover’ (1965)

'Inside Daisy Clover' (1965)
Warner Bros. Pictures

In this musical drama, Redford plays Wade Lewis, a handsome and mysterious movie star in 1930s Hollywood. The film’s main character is Daisy Clover, a teenage tomboy who becomes a famous actress. She falls for the dashing Wade Lewis and they get married, but she soon discovers that he is hiding his true self and has his own secret reasons for marrying her.

The role of Wade Lewis was a significant step for Redford, establishing him as a compelling romantic figure with a dark side. He portrays the character as a classic Hollywood idol who is secretly bisexual and deeply troubled. His charm masks a deep unhappiness, and his relationship with Daisy ends in heartbreak. The part showcased Redford’s ability to play complex, conflicted characters beneath a handsome exterior.

‘Situation Hopeless — But Not Serious’ (1965)

'Situation Hopeless — But Not Serious' (1965)
Paramount Pictures

This quirky comedy is set in Germany at the end of World War II. Redford plays Captain Hank Wilson, an American airman whose plane is shot down. He and his fellow soldier are captured by a lonely and eccentric German civilian named Wilhelm Frick. Frick keeps them as prisoners in his cellar for years, long after the war has ended, because he enjoys their company and does not want to be alone again.

Redford’s role is largely comedic, as he and his friend must deal with their strange and deluded captor. They eventually become comfortable in their bizarre situation, learning to live with the man who has tricked them into believing the war is still going on. The film is a dark farce, and Redford’s performance highlights the absurd humor of the characters’ predicament.

‘This Property Is Condemned’ (1966)

'This Property Is Condemned' (1966)
Paramount Pictures

Based on a one-act play by Tennessee Williams, this film paired Robert Redford with Natalie Wood. Redford plays Owen Legate, a railroad official who comes to a small Mississippi town during the Great Depression. His job is to lay off many of the local railroad workers. While there, he meets Alva Starr, the town’s flirtatious and tragic dreamer, and they begin a passionate and doomed romance.

The role of Owen Legate established Redford as a serious dramatic actor and a romantic lead. He is the quiet, handsome stranger who represents a chance for Alva to escape her small-town life. The chemistry between Redford and Wood is central to the film’s power. The movie, directed by Sydney Pollack, was the first of many successful collaborations between the actor and director.

‘The Chase’ (1966)

'The Chase' (1966)
Horizon Pictures

‘The Chase’ is a tense drama with an all-star cast that explores the dark side of a small Texas town. The story unfolds as a local man, Bubber Reeves, escapes from prison and is believed to be heading back home. Robert Redford plays the escaped convict, Charlie ‘Bubber’ Reeves. His return brings out the worst in the townspeople, exposing their hypocrisy, corruption, and violence.

Although Redford’s character is the catalyst for the events, he spends much of the film on the run, off-screen. The movie focuses more on the town’s reaction to his escape, led by the sheriff played by Marlon Brando. When Bubber does appear, he is a sympathetic figure, wrongfully accused and caught in a storm of chaos he did not create. The role continued to build Redford’s image as a compelling anti-hero.

‘Barefoot in the Park’ (1967)

'Barefoot in the Park' (1967)
Paramount Pictures

This romantic comedy, based on the Neil Simon play, paired Robert Redford with Jane Fonda. Redford plays Paul Bratter, a straight-laced, conservative young lawyer who has just married the free-spirited Corie. The film follows the newlyweds as they adjust to married life in a tiny, fifth-floor walk-up apartment in New York City. Paul’s cautious nature clashes with Corie’s impulsive and fun-loving personality, leading to a series of funny and touching conflicts.

The role of Paul Bratter established Redford as a major romantic lead. His on-screen chemistry with Fonda was perfect, and he skillfully balanced the character’s stuffiness with a likable charm. The film was a huge box office success and showcased his talent for comedy. It proved that he could be more than just a handsome face, turning him into a bankable Hollywood star and setting the stage for his iconic roles in the years to come.

‘Butch Cassidy and the Sundance Kid’ (1969)

'Butch Cassidy and the Sundance Kid' (1969)
20th Century Fox

In this classic Western, Robert Redford plays the Sundance Kid, the quiet, fast-drawing partner of the charming outlaw Butch Cassidy, played by Paul Newman. The film follows the two friends as they rob banks and trains in the American West. When the law starts to close in, they flee to Bolivia with their companion, Etta Place, in hopes of starting a new life. The story is famous for its blend of humor, action, and buddy-comedy dynamics.

This film turned Robert Redford into a superstar. His pairing with Paul Newman is one of the most celebrated in movie history, and their easy chemistry became the heart of the film. As the cool, reserved Sundance, Redford was the perfect counterpart to Newman’s talkative and clever Butch. The role defined his image as a charismatic, anti-heroic figure and remains one of his most beloved and iconic performances.

‘Tell Them Willie Boy Is Here’ (1969)

'Tell Them Willie Boy Is Here' (1969)
Universal Pictures

This Western is a grim and thought-provoking story based on true events. It tells the tale of a Native American man named Willie Boy who is hunted by the law after killing his girlfriend’s father in self-defense. Robert Redford stars as Deputy Sheriff Christopher ‘Coop’ Cooper, the man tasked with leading the manhunt across the desert.

The character of Coop is a modern lawman who is uncomfortable with the old ways of the West. He is a reluctant hero who understands the injustice of the situation but must still do his job. The film is a commentary on racism and the clash of cultures. Redford’s performance is quiet and internal, portraying a man who is caught between his duty and his conscience.

‘Downhill Racer’ (1969)

'Downhill Racer' (1969)
Paramount Pictures

‘Downhill Racer’ is a realistic and unsentimental look at the world of competitive skiing. Redford plays David Chappellet, a ruthlessly ambitious and talented skier from a small town who joins the U.S. ski team. Chappellet is arrogant, selfish, and single-mindedly focused on becoming an Olympic champion. He clashes with his coach and teammates, caring only about winning.

Redford was instrumental in getting this film made, wanting to show the dark side of professional sports. His portrayal of Chappellet is unflinching, creating a character who is not particularly likable but is fascinating to watch. The film is known for its thrilling and realistic ski sequences, many of which Redford performed himself. It is a powerful character study of what it takes to be the best.

‘Little Fauss and Big Halsy’ (1970)

'Little Fauss and Big Halsy' (1970)
Paramount Pictures

This film explores the world of professional motorcycle racing. Redford plays Halsy Knox, a charismatic, womanizing, and dishonest motorcycle racer. He befriends a naive and awkward amateur racer named Little Fauss. Halsy uses Little’s mechanical skills and good nature for his own selfish benefit, all while pursuing fame on the racing circuit.

The role of Halsy Knox allowed Redford to play a character who was charming on the surface but deeply flawed underneath. He is a user and a liar, but his confidence and good looks make him irresistible to those around him. The film is a character study of two very different men trying to make their mark in a competitive and gritty world.

‘Jeremiah Johnson’ (1972)

'Jeremiah Johnson' (1972)
Warner Bros. Pictures

In this iconic Western, Redford plays a veteran of the Mexican-American War who decides to leave civilization behind and become a mountain man in the Rocky Mountains. The film follows his journey as he learns to survive in the harsh wilderness, battling the elements and forging uneasy relationships with the local Native American tribes. He builds a life for himself, but it is ultimately shattered by violence.

‘Jeremiah Johnson’ was a passion project for Redford and became one of his signature roles. His performance is largely silent, conveying the character’s strength and isolation through his physical presence. The film is celebrated for its stunning cinematography and its realistic depiction of mountain life. It is a powerful story of one man’s search for peace and his struggle against an unforgiving frontier.

‘The Candidate’ (1972)

'The Candidate' (1972)
Warner Bros. Pictures

‘The Candidate’ is a sharp political satire in which Redford stars as Bill McKay, an idealistic, unknown lawyer who is convinced to run for the U.S. Senate. Initially, he agrees to run because he is promised he can say whatever he wants, as he has no chance of winning. However, as his campaign gains unexpected momentum, he is forced to compromise his strong principles and water down his message to appeal to more voters.

The film offers a cynical and insightful look at the American political process. Redford’s performance perfectly captures the journey of a well-meaning man who slowly loses his integrity in the pursuit of power. The movie’s final, famous line, “What do we do now?”, spoken by McKay after his victory, is a powerful statement on the emptiness of modern politics. The role showed Redford’s serious side and his interest in making films with a social message.

‘The Hot Rock’ (1972)

'The Hot Rock' (1972)
20th Century Fox

This lighthearted heist film features Redford as John Dortmunder, a professional thief who has just been released from prison. He is immediately hired to steal a valuable diamond from a museum. Dortmunder assembles a team of experts, but the seemingly simple heist turns into a series of comical disasters, forcing the team to steal the same diamond over and over again from different locations.

‘The Hot Rock’ is a clever and entertaining caper film that showcases Redford’s comedic timing. His character, Dortmunder, is a perpetually unlucky but persistent professional who is constantly frustrated by the increasingly absurd challenges he faces. The film is known for its witty script and the great chemistry among its ensemble cast.

‘The Sting’ (1973)

'The Sting' (1973)
Universal Pictures

Reuniting with his ‘Butch Cassidy’ co-star Paul Newman and director George Roy Hill, ‘The Sting’ was a massive critical and commercial success. Redford plays Johnny Hooker, a small-time grifter in 1930s Chicago. After his partner is murdered by a ruthless crime boss, Hooker seeks out the legendary con man Henry Gondorff, played by Newman, to help him get revenge. Together, they assemble a team to pull off an elaborate and complicated con on the man responsible.

The film won seven Academy Awards, including Best Picture, and Redford earned his only Oscar nomination for acting. His performance as the slick, ambitious, and sometimes naive Hooker is a masterclass in charm and timing. The incredible chemistry between Redford and Newman is once again the film’s biggest strength. ‘The Sting’ is a clever, stylish, and endlessly entertaining movie that cemented Redford’s status as one of the biggest stars in the world.

‘The Way We Were’ (1973)

'The Way We Were' (1973)
Columbia Pictures

‘The Way We Were’ is a classic romantic drama that chronicles the decades-long, on-again, off-again relationship between two very different people. Redford plays Hubbell Gardiner, a handsome, popular, and easygoing writer with a natural talent for success. He falls in love with Katie Morosky, a passionate and politically active woman played by Barbra Streisand. Their love is tested by their fundamental differences in personality and beliefs.

The role of Hubbell Gardiner is one of Redford’s most famous romantic parts. He embodies a kind of effortless, golden-boy charm that contrasts sharply with Streisand’s intense and outspoken character. The film explores whether love is enough to overcome deep personal and political divides. The powerful chemistry between the two leads made ‘The Way We Were’ a massive box office hit and an enduring romance classic.

‘The Great Gatsby’ (1974)

'The Great Gatsby' (1974)
Paramount Pictures

In this lavish adaptation of F. Scott Fitzgerald’s classic novel, Robert Redford plays the title role of Jay Gatsby. Gatsby is a mysterious and fabulously wealthy millionaire who throws extravagant parties at his Long Island mansion in the 1920s. It is eventually revealed that his entire fortune and grand lifestyle are all part of a desperate attempt to win back the love of his life, Daisy Buchanan, who is now married to another man.

Playing Jay Gatsby was a major undertaking, as the character is one of the most famous in American literature. Redford brought his signature charisma to the role, but also captured the character’s deep sense of loneliness, obsession, and hope. He portrays Gatsby as a man who has built a fantasy world around himself, one that is destined to crumble.

‘Three Days of the Condor’ (1975)

'Three Days of the Condor' (1975)
Paramount Pictures

In this paranoid thriller, Robert Redford plays Joe Turner, a low-level CIA analyst whose code name is “Condor.” His job is to read books, looking for hidden codes and new ideas. One day, he returns from lunch to find that all of his co-workers have been murdered. Turner goes on the run, not knowing who he can trust, as he tries to uncover a vast conspiracy from within the CIA itself.

This film is a classic 1970s conspiracy thriller that captured the era’s post-Watergate distrust of government. Redford is perfectly cast as the ordinary man caught in an extraordinary and dangerous situation. He portrays Turner’s intelligence and growing desperation with a quiet intensity that keeps the audience on edge. ‘Three Days of the Condor’ became a benchmark for the genre and remains one of Redford’s most compelling and popular films.

‘The Great Waldo Pepper’ (1975)

'The Great Waldo Pepper' (1975)
Universal Pictures

This adventure film reunites Redford with director George Roy Hill. He plays Waldo Pepper, a disillusioned World War I pilot who missed out on the chance to fly in combat. In the 1920s, he makes a living as a barnstorming pilot, performing dangerous stunts for small-town crowds. He dreams of fame and of facing off against a legendary German flying ace, all while the golden age of aviation is coming to an end.

The role allowed Redford to showcase his daredevil side, as he performed many of his own flying stunts. He portrays Waldo Pepper as a man clinging to a past that never was, a dreamer who refuses to let go of his passion for flight. The film is a nostalgic and exciting tribute to the early days of aviation and the pilots who risked their lives for the thrill of it.

‘All the President’s Men’ (1976)

'All the President's Men' (1976)
Wildwood Enterprises

‘All the President’s Men’ tells the true story of how Washington Post reporters Bob Woodward and Carl Bernstein uncovered the Watergate scandal, which led to the resignation of President Richard Nixon. Robert Redford, who also produced the film, plays Bob Woodward. The movie follows Woodward and his partner Bernstein, played by Dustin Hoffman, as they investigate the initial break-in at the Watergate complex and slowly piece together a conspiracy that reaches the highest levels of government.

This film is considered one of the greatest journalism movies ever made. Redford’s portrayal of Woodward is focused and determined, capturing the meticulous work of an investigative reporter. He and Hoffman create a believable partnership, showing the tension and collaboration involved in their historic investigation. The film was a huge success and showed Redford’s commitment to producing intelligent, politically relevant films.

‘A Bridge Too Far’ (1977)

'A Bridge Too Far' (1977)
United Artists

This epic war film depicts Operation Market Garden, a failed Allied attempt to seize a series of bridges in the Netherlands during World War II. The movie features a massive ensemble cast of stars, with Redford in a key role. He plays Major Julian Cook, who leads his paratroopers in a desperate and heroic daylight river crossing under heavy enemy fire to capture a crucial bridge.

Although his screen time is limited in such a large cast, Redford’s sequence is one of the most memorable and intense in the film. His portrayal of Major Cook is one of quiet courage and unwavering leadership in the face of impossible odds. The role added another heroic figure to his filmography and showed his ability to make a strong impact in a supporting part.

‘The Electric Horseman’ (1979)

'The Electric Horseman' (1979)
Columbia Pictures

Reuniting with Jane Fonda, this film is a modern Western with a comedic and romantic touch. Redford plays Sonny Steele, a former five-time world champion rodeo cowboy who is now reduced to being a corporate spokesman for a breakfast cereal. Disgusted with his life and how a valuable champion horse is being treated, he decides to steal the horse and ride off into the desert to set it free.

Sonny is a classic Redford character: a rugged individualist who stands up for his principles against a corrupt system. His journey is chronicled by a determined television reporter, played by Fonda, who eventually joins his cause. The film was a major box office hit, thanks to the undeniable chemistry between its two leads and its charming story of rebellion and romance.

‘Brubaker’ (1980)

'Brubaker' (1980)
20th Century Fox

Based on a true story, ‘Brubaker’ stars Redford as Henry Brubaker, the new warden of a notoriously corrupt and violent prison in the South. He first enters the prison undercover, posing as an inmate to experience the horrific conditions and abuse firsthand. After revealing his identity, he begins a massive and dangerous campaign to reform the brutal institution, fighting against a system of corruption that reaches the highest levels of state government.

The role of Henry Brubaker is one of Redford’s most serious and intense. He plays the character as a man of unwavering integrity and determination, willing to risk his career and his life to bring justice to a broken system. The film is a powerful indictment of prison corruption and a compelling drama about one man’s fight for what is right.

‘The Natural’ (1984)

'The Natural' (1984)
TriStar Pictures

‘The Natural’ is a mythic baseball story about Roy Hobbs, a player with incredible, almost magical talent. After his early career is cut short by a violent incident, Hobbs disappears for years. He returns to the major leagues as a middle-aged rookie, joining a losing team and leading them on an unbelievable journey to the pennant. The film is a classic American fable about second chances and chasing a dream.

Robert Redford’s portrayal of Roy Hobbs is one of his most iconic roles. He perfectly embodies the quiet, mysterious, and determined hero, creating a character that feels larger than life. The film has a timeless, nostalgic quality, and its final home run scene is one of the most famous moments in sports movie history. ‘The Natural’ was a major comeback for Redford and remains a beloved classic.

‘Out of Africa’ (1985)

'Out of Africa' (1985)
Universal Pictures

This sweeping romantic epic won the Academy Award for Best Picture. The film is based on the life of Karen Blixen, who moves from Denmark to Kenya to run a coffee plantation. There, she meets and falls in love with Denys Finch Hatton, a charismatic big-game hunter played by Robert Redford. Their love story unfolds against the stunning backdrop of the African landscape.

Redford’s character is a charming, independent adventurer who resists being tied down. He represents a sense of freedom and a deep connection to nature. His chemistry with Meryl Streep’s Karen is at the heart of the film’s emotional power. ‘Out of Africa’ was a huge international success and showcased Redford’s enduring appeal as a classic romantic leading man in a grand, old-fashioned Hollywood movie.

‘Legal Eagles’ (1986)

'Legal Eagles' (1986)
Universal Pictures

This film is a lighthearted legal comedy-thriller. Redford plays Tom Logan, a successful and serious assistant district attorney. His life is turned upside down when he gets involved with a quirky defense attorney and her eccentric client, a performance artist who is accused of theft and murder. Logan must team up with the two women to solve the case, which involves the high-stakes world of the New York art scene.

‘Legal Eagles’ gave Redford a chance to return to a more comedic role, playing the straight man in a chaotic situation. He stars alongside Debra Winger and Daryl Hannah, and the film blends courtroom drama, mystery, and romantic comedy. The role of Tom Logan is that of a man whose orderly life is disrupted by unpredictable women and dangerous criminals.

‘Havana’ (1990)

'Havana' (1990)
Universal Pictures

Set in Cuba in 1958, on the eve of the revolution, this film stars Redford as Jack Weil, an American professional gambler. He travels to Havana looking for a big poker game, but finds himself entangled in the political turmoil. He falls for the beautiful wife of a revolutionary, and his detached, cynical worldview is challenged as he is drawn into the conflict.

The film was a reunion for Redford and director Sydney Pollack. The character of Jack Weil is a classic anti-hero, a man who lives by his own code but is ultimately forced to take a side. The movie is a grand, old-fashioned romance set against a dramatic historical backdrop, attempting to capture the style of classics like ‘Casablanca’.

‘Sneakers’ (1992)

'Sneakers' (1992)
Universal Pictures

‘Sneakers’ is a smart and fun heist comedy with an all-star cast. Redford leads the team as Martin Bishop, a former radical who now runs a group of security experts. They specialize in testing the security systems of banks and other institutions. Bishop and his eccentric team are hired by the government to retrieve a mysterious black box, but they soon discover that the device has the power to decode any encryption system, making it incredibly dangerous.

The film is a lighthearted and intelligent thriller that benefits from the amazing chemistry of its ensemble cast. Redford is the calm, cool center of the group, playing the reluctant leader with his signature charm. ‘Sneakers’ was a box office hit and has since become a cult classic, praised for its clever script and timely themes about information and privacy. It was a perfect role for Redford, blending his dramatic intensity with a lighter, comedic touch.

‘Incident at Oglala’ (1992)

'Incident at Oglala' (1992)
Spanish Fork Motion Picture

In this powerful documentary, Robert Redford serves as the narrator. The film investigates the events surrounding a 1975 shootout on the Pine Ridge Indian Reservation, which resulted in the deaths of two FBI agents and one Native American man. The documentary argues that Leonard Peltier, the man convicted for the agents’ murders, was wrongly imprisoned.

While he does not appear on screen, Redford’s voice guides the audience through the complex and controversial story. His involvement brought significant attention to the case and reflected his long-standing interest in Native American rights and social justice issues. His clear and authoritative narration helps to lay out the film’s compelling argument for Peltier’s innocence.

‘Indecent Proposal’ (1993)

'Indecent Proposal' (1993)
Paramount Pictures

This drama was one of the most talked-about films of its time. Redford plays John Gage, a handsome and charismatic billionaire. He meets a young married couple who are in financial trouble at a Las Vegas casino. Gage makes them a shocking offer: one million dollars for a night with the wife. The couple’s decision to accept the proposal tests their relationship in ways they never imagined.

The role of John Gage is that of a smooth and powerful man who believes that anything can be bought. Redford plays the character not as a simple villain, but as a complex and lonely figure who uses his wealth to control the world around him. The film was a huge commercial success and sparked widespread debate about its moral premise.

‘La Classe américaine’ (1993)

'La Classe américaine' (1993)
Dune

This unique French television film, also known as ‘Le Grand Détournement’, is a comedy created entirely by editing and re-dubbing clips from old Warner Bros. movies. The story is a bizarre parody of ‘Citizen Kane’, centered on the death of a man named George Abitbol. Robert Redford appears as “Steven,” but his performance consists of repurposed footage from ‘All the President’s Men’.

The French filmmakers dubbed over the original dialogue with their own comedic script, placing the famous actors in a completely new and absurd story. Redford’s “role” is therefore not a traditional performance but a clever and funny use of his existing work. The film has become a cult classic in France for its inventive and hilarious concept.

‘Up Close & Personal’ (1996)

'Up Close & Personal' (1996)
Cinergi Pictures

In this romantic drama, Redford plays Warren Justice, a veteran television news director. He discovers a promising but inexperienced young woman named Tally Atwater and becomes her mentor. He guides her career from a local weather girl to a top national news anchor. Along the way, their professional relationship blossoms into a deep and complicated romance.

The film explores the high-pressure world of broadcast journalism and the sacrifices required for success. Redford’s character is a tough, principled journalist who sees great potential in Tally. His chemistry with co-star Michelle Pfeiffer drives the story. The role of the wise and world-weary mentor became a common one for Redford in the later stages of his career.

‘The Horse Whisperer’ (1998)

'The Horse Whisperer' (1998)
Wildwood Enterprises

In this film, which he also directed, Redford plays Tom Booker, a gifted “horse whisperer” with a unique ability to heal troubled horses. He is hired by a New York magazine editor to help her traumatized daughter and her daughter’s severely injured horse after a tragic riding accident. Booker’s patient and calm approach helps heal not only the horse and the young girl but also the girl’s anxious mother.

‘The Horse Whisperer’ was a major success and was praised for its stunning cinematography and emotional depth. Redford’s performance as the quiet, rugged, and wise cowboy is central to the film’s appeal. The character embodies a connection to nature and a simpler way of life, themes that have been important throughout Redford’s career. It was a perfect role for him as both an actor and a director, showcasing his love for the American West.

‘The Last Castle’ (2001)

'The Last Castle' (2001)
DreamWorks Pictures

Redford stars as Lieutenant General Eugene Irwin, a highly decorated and respected three-star general who is sent to a maximum-security military prison. He was court-martialed for disobeying a presidential order. Once inside, he is appalled by the cruel and unjust methods of the prison’s warden. Irwin uses his leadership skills to rally his fellow inmates and lead them in a rebellion to take control of the prison.

The role of General Irwin is that of a brilliant military strategist and a man of immense integrity. Redford portrays him as a quiet but powerful leader who earns the respect of the other prisoners. The film is a tense action-drama about honor, leadership, and the fight against tyranny.

‘Spy Game’ (2001)

'Spy Game' (2001)
TOHO

In this spy thriller, Redford plays Nathan Muir, a veteran CIA case officer on his last day before retirement. He learns that his protégé, Tom Bishop, played by Brad Pitt, has been captured in China and is scheduled to be executed. As Muir is debriefed by his superiors, the story of his complex relationship with Bishop is told through a series of flashbacks. Muir must use all his skills to orchestrate a rogue rescue mission without the CIA’s approval.

The film cleverly pairs the veteran Redford with the younger Pitt, creating a dynamic of mentor and student. Redford’s character is a cynical and manipulative old-school spy who is ultimately forced to risk everything for loyalty. His performance is cool, calculated, and intelligent, making Muir a compelling and memorable character.

‘The Clearing’ (2004)

'The Clearing' (2004)
Fox Searchlight Pictures

‘The Clearing’ is a tense thriller in which Redford plays Wayne Hayes, a wealthy and successful executive who appears to have a perfect life. One day, he is kidnapped from his home by a disgruntled former employee. The film cuts between two storylines: Wayne’s attempts to outwit his captor in the woods, and his wife’s struggle to deal with the FBI investigation, which uncovers secrets about her husband’s life.

The role gave Redford the chance to play a man stripped of his power and forced to confront his past mistakes. The film is a quiet and suspenseful character study rather than a typical action-thriller. Redford’s performance captures the fear and regret of a man whose carefully constructed life is falling apart.

‘An Unfinished Life’ (2005)

'An Unfinished Life' (2005)
Miramax

In this family drama, Redford plays Einar Gilkyson, a grizzled and retired Wyoming rancher living a life of bitterness and regret. He blames his daughter-in-law, Jean, for the death of his son in a car accident years ago. His world is turned upside down when Jean shows up at his ranch with her young daughter, the granddaughter Einar never knew he had, seeking refuge from an abusive relationship.

The film is a story of healing and forgiveness. Redford’s character is a stubborn and emotionally closed-off man who must learn to let go of his anger. His interactions with his granddaughter slowly begin to break down the walls he has built around himself. It is a touching performance that explores the slow process of mending a broken family.

‘Charlotte’s Web’ (2006)

'Charlotte's Web' (2006)
Paramount Pictures

In this live-action adaptation of the classic children’s book, Robert Redford provides the voice for Ike, the horse in the barn. The story is about the friendship between a pig named Wilbur and a spider named Charlotte, who tries to save Wilbur from being slaughtered by weaving words about him in her web. Ike the horse is one of the many barnyard animals who witness this miracle.

Redford’s role is a small but memorable voice part. As Ike, he is initially spooked by the “magic” of the writing in the web, but he is a friendly and supportive member of the barn community. His warm and familiar voice adds to the film’s nostalgic and gentle tone.

‘Lions for Lambs’ (2007)

'Lions for Lambs' (2007)
Wildwood Enterprises

Redford directed and starred in this political drama, which tells three interconnected stories happening at the same time. Redford plays Professor Stephen Malley, a political science professor at a California university. He is trying to inspire a gifted but cynical student to become more engaged in the world. Meanwhile, two of his former students are fighting in Afghanistan, and a charismatic senator is giving a major television interview about a new war strategy.

The film is a critique of American foreign policy and public apathy. Redford’s character represents the voice of idealism and intellectual debate, urging the younger generation to take action. The movie is driven by intense conversations rather than action, reflecting Redford’s desire to make films that tackle important political and social questions.

‘The Company You Keep’ (2012)

'The Company You Keep' (2012)
Brightlight Pictures

In this thriller, which he also directed, Redford plays Jim Grant, a public interest lawyer and single father. His quiet life is shattered when his true identity is revealed by a young reporter. Grant is actually Nick Sloan, a former member of the militant anti-war group the Weather Underground, who has been a fugitive for decades. He must go on the run to find the one person who can clear his name.

The film explores the legacy of 1960s radicalism and the choices people make in their youth. Redford’s character is a man forced to confront his past and protect his family. It is a smart, character-driven thriller that features an impressive ensemble cast of veteran actors.

‘All Is Lost’ (2013)

'All Is Lost' (2013)
Universal Pictures

‘All Is Lost’ is a remarkable survival drama featuring Robert Redford in a nearly silent, solo performance. He plays an unnamed man who is on a solo voyage across the Indian Ocean. His journey takes a disastrous turn when his sailboat collides with a shipping container, leaving him stranded and fighting for his life against the elements. The film follows his desperate and resourceful struggle to survive.

This film is a stunning showcase for Redford’s acting talent. With almost no dialogue, he has to convey his character’s fear, determination, and resilience through his actions and expressions alone. It is a powerful and physically demanding performance that earned him widespread critical acclaim. The role proved that even late in his career, Redford was still capable of delivering a commanding and unforgettable performance.

‘Captain America: The Winter Soldier’ (2014)

'Captain America: The Winter Soldier' (2014)
Marvel Studios

Entering the Marvel Cinematic Universe, Redford took on the role of Alexander Pierce, a senior leader within the intelligence agency S.H.I.E.L.D. and a member of the World Security Council. Pierce is a respected and powerful figure who is a close friend of Nick Fury. However, it is revealed that he is secretly a high-ranking leader of Hydra, a terrorist organization that has been secretly operating within S.H.I.E.L.D. for decades.

The role was a surprising and effective turn for Redford, casting him as a smooth, charismatic villain. He brought a sense of gravitas and old-school thriller style to the superhero blockbuster. His character’s betrayal is a major turning point in the Marvel universe, and Redford’s presence lent a level of prestige to the film.

‘A Walk in the Woods’ (2015)

'A Walk in the Woods' (2015)
Wildwood Enterprises

This comedy is based on the memoir by travel writer Bill Bryson. Redford plays Bryson, who, after returning to the U.S., decides to hike the entire 2,200-mile Appalachian Trail. Against the advice of his wife, he sets off on the adventure, accompanied by his long-lost and out-of-shape friend, Stephen Katz, an old friend he has a troubled history with.

The film is a buddy comedy that follows the two mismatched friends as they struggle with the challenges of the trail and confront their own mortality. Redford, who also produced the film, captures Bryson’s dry wit and intellectual curiosity. It is a charming and funny story about friendship and the call of the wild.

‘Truth’ (2015)

'Truth' (2015)
PRC Productions

In ‘Truth’, Redford portrays the legendary CBS newsman Dan Rather. The film chronicles the 2004 controversy surrounding a ’60 Minutes’ report about President George W. Bush’s military service record. The story, produced by Mary Mapes, came under fire when the documents it was based on were questioned as forgeries. The scandal ultimately led to the end of Rather’s career at CBS News.

Redford’s performance captures the famous anchor’s familiar mannerisms and unwavering dedication to journalism. The film is a defense of Rather and his producer, arguing that they were victims of a political and corporate smear campaign. It is a gripping drama about the pressures and responsibilities of the modern news media.

‘Pete’s Dragon’ (2016)

'Pete's Dragon' (2016)
Whitaker Entertainment

In this live-action remake of the Disney classic, Redford plays Conrad Meacham, a local wood carver and the town’s old-timer. He has spent years telling local children stories about a mysterious dragon that lives in the nearby woods. His daughter, a park ranger, dismisses these as tall tales, until she meets a young orphan boy named Pete who claims to have lived in the forest for years with his best friend, a giant green dragon named Elliot.

The role of Meacham is that of the wise and gentle storyteller who has kept the magic of the forest alive. Redford brings a warm, grandfatherly presence to the film. He is the one character who always believed in the existence of the dragon, representing a sense of wonder and a connection to the natural world.

‘The Discovery’ (2017)

'The Discovery' (2017)
Protagonist Pictures

This science fiction film is set in a world where the existence of an afterlife has been scientifically proven. Redford plays Thomas Harbor, the physicist responsible for this groundbreaking and dangerous discovery. His finding has led to a global wave of suicides, as people choose to “get there” rather than continue with their lives. The story follows his son, who falls in love with a troubled woman while visiting his father’s isolated research compound.

Redford portrays Harbor as a brilliant but haunted man, burdened by the unforeseen consequences of his work. He is a remote and morally ambiguous figure, continuing his research despite the chaos it has caused. The film is a moody and thought-provoking exploration of love, death, and regret.

‘Our Souls at Night’ (2017)

'Our Souls at Night' (2017)
Wildgaze Films

Reuniting with Jane Fonda for the fourth and final time, this quiet drama tells the story of two lonely neighbors in a small Colorado town. Redford plays Louis Waters, a widower who lives alone. His neighbor, Addie Moore, also a widow, makes him a surprising proposal: she asks if he would be willing to come over and sleep in her bed at night, platonically, just to have someone to talk to and ease the loneliness.

The film is a gentle and touching story about companionship in later life. The natural, easy chemistry between Redford and Fonda, honed over 50 years, is the heart of the movie. Redford’s performance is understated and moving, portraying a kind man who is given a second chance at connection and happiness.

‘The Old Man & the Gun’ (2018)

'The Old Man & the Gun' (2018)
Condé Nast Entertainment

In what he has called his final acting role, Robert Redford plays Forrest Tucker, a real-life career criminal and prison escape artist. The film follows Tucker in his 70s as he continues to rob banks with a polite and gentlemanly charm. Despite his age, he has no intention of retiring from his life of crime. He is pursued by a determined detective and also strikes up a romance with a woman who is charmed by his personality.

The role of Forrest Tucker is a perfect send-off for Redford’s acting career. The character is charismatic, charming, and a little bit roguish, echoing many of the iconic roles he played throughout his career. The film is a gentle and nostalgic tribute to its star, allowing him to display the effortless screen presence that made him a legend. It serves as a fitting and poignant farewell to one of Hollywood’s greatest actors.

‘Buttons’ (2018)

'Buttons' (2018)
Buttons

In this musical fairytale, Robert Redford serves as the narrator, playing a guardian angel. The story follows the journey of a young orphan girl named Annabelle during the Christmas season. When she is at her lowest point, her guardian angel helps guide her and protect her, teaching her about hope and faith.

Redford’s role is a comforting and authoritative voice that guides the audience through the magical, holiday-themed story. Though he is not seen, his narration provides the film with a sense of warmth and wonder. It is a small but important part in a family-friendly Christmas movie.

‘Avengers: Endgame’ (2019)

'Avengers: Endgame' (2019)
Marvel Studios

Robert Redford made a surprise cameo appearance in the biggest movie of the Marvel Cinematic Universe, reprising his role as Alexander Pierce. His appearance is part of the “time heist” sequence, where some of the Avengers travel back to the year 2012. They encounter Pierce in his S.H.I.E.L.D. office during the events of the first ‘Avengers’ film.

The brief cameo was a treat for fans, bringing Redford’s character back one last time. It was achieved using a combination of new footage and digital de-aging technology to make him look as he did in his earlier Marvel appearance. It was a fun and unexpected way for the legendary actor to be part of one of the biggest movie events in history.

‘Omniboat: A Fast Boat Fantasia’ (2020)

'Omniboat: A Fast Boat Fantasia' (2020)
Borscht Corp.

This is a wild and experimental film made by a collective of Miami-based filmmakers. The movie tells the surreal and bizarre life story of a speedboat named Layin’ Low. The boat goes on a series of strange adventures throughout Miami, encountering a wide range of odd characters. Robert Redford has a small, strange role in this very unconventional film.

In a brief and memorable sequence, Redford plays a character who has a strange obsession with dolphins. His part is just one piece of the film’s chaotic and fantastical narrative. His involvement in such an avant-garde and bizarre project so late in his career was a complete surprise and showed his willingness to support unique and independent filmmaking.

Share which Robert Redford performance you believe best defines his legendary career in the comments below.

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