Robert Redford’s career highlights span over six decades, marked by unexpected decisions and complex roles that challenged his public image. In 1963, director Mike Nichols noticed Redford’s considerable talent and charisma, casting him in Neil Simon’s Broadway play Barefoot in the Park. Redford portrayed a cautious newlywed learning to embrace spontaneity, and this collaboration led Nichols to cast him again for the 1966 film adaptation of Edward Albee’s play, Who’s Afraid of Virginia Woolf?, aiming to showcase Redford as an ambitious yet naive college professor. Surprisingly, Redford declined this role, as he disliked the character’s vulnerability.
Redford’s early career decisions reflected a reluctance to play weakened or “loser” characters, a trait noted by Nichols who later cast another actor for a different project. When Nichols sought Redford for the lead in The Graduate (1967), Redford eagerly pursued the role of Benjamin Braddock. However, Nichols rejected him, citing Redford’s inability to convincingly portray a directionless young man. Nichols recalled:
“I was playing pool with him, and said, ‘I’m really sad, but you can’t do it. You can’t play a loser.’ He said, ‘Of course I can play a loser!’ I said, ‘You can’t! Look at you! How many times have you struck out with a woman?’”
Mike Nichols
“And he said, I swear to you, ‘What do you mean?’ He didn’t even understand the concept. To him, it was like saying, ‘How many times have you been to a restaurant and not had a meal?’”
Mike Nichols
As Nichols indicated, Redford radiated the confident assurance of someone who anticipated inevitable success, rarely embodying doubt or failure on screen during his early years.
Breaking the Mold: Roles That Defied Expectations
Despite losing the Graduate role to Dustin Hoffman, Redford soon chose more challenging characters that contrasted with his “golden boy” image. In 1969, he took on the lead in Downhill Racer, directed by Michael Ritchie, marking Ritchie’s feature film debut. Redford portrayed David Chappellet, a talented but self-centered skier on the U.S. Olympic team who alienates teammates and lovers with his single-minded ambition. The role was reportedly part of a settlement with Paramount after Redford passed on the lead in Blue, a western that later became notorious for its failures.
David Chappellet’s character was driven by a desire to rise above his humble roots in a Colorado town, yet his relationship with his father revealed a lack of encouragement. When Chappellet expressed his determination to become a champion at all costs, his father dismissed the ambition with, “The world’s full of them.” Hence, Chappellet obsessively pursued victory, evident in his answer to a reporter’s inquiry about life after the Olympics:
“This is it. Nothing else matters.”
Two years later, Redford reunited with Ritchie in The Candidate (1972), portraying Bill McKay, a passionate lawyer pressured into a political campaign. With guidance from a cynical consultant named Marvin Lucas, McKay gradually dilutes his ideals to appeal to voters and ultimately wins a Senate seat. Yet, the film’s closing moment, with McKay asking “What do we do now?” highlights lingering ambiguity about political success and compromise.
Reflecting on these complex roles, Redford explained in a 1994 interview:
“In a lot of the films I’ve been able to design or produce, like Downhill Racer, The Candidate, Jeremiah Johnson, All the President’s Men — there’s a common theme of discovery in the last frame. The character goes through believing one thing and then gets to the end and finds that life works a little differently. And there’s a shock on the character’s face when he realizes at the last moment, Holy shit! This is how this works! It isn’t like I thought at all!”
Robert Redford
Exploring the American Dream and Disillusionment Through Film
Redford’s body of work often interrogated the American Dream’s complexities and contradictions. He directed and starred in Quiz Show (1994), a dramatization of the 1950s quiz show scandals, focusing on a congressional aide exposing corrupt rigging in the game show Twenty-One. The story revealed how corporate interests manipulated media for profit, ruining the reputations of beloved contestants.
Redford elaborated on this recurring theme, sharing:
“A lot of the work I’ve done has involved looking at the American Dream, from all different ways, because I was fed such a dose of it when I was a kid. I was given this legacy as a kid about how you’re supposed to play the game to get ahead in life. I didn’t realize that it was a false legacy, that it wasn’t true when they said, ‘It’s not whether you win or lose, it’s how you play the game.’ Because the fact is, for most people, the only thing that matters is whether you win or lose.”
Robert Redford
This theme resonates in films spanning decades, including The Great Gatsby (1974), with Redford as the tragic titular figure, and Three Days of the Condor (1975), in which his CIA analyst character’s fate is shrouded in uncertainty after uncovering government corruption. The 1980 film Brubaker features Redford as a prison warden struggling to reform a brutal system, further exploring disillusionment with institutional authority.
Darker Characters and Challenging Performances
A notable departure from his typical roles came in Sidney J. Furie’s 1970 film Little Fauss and Big Halsy, where Redford played Halsy Knox, a ruthless dirt bike racer whose unscrupulous and selfish nature alienates those around him. Despite promotional efforts emphasizing Redford’s physical allure, the movie’s core stressed Halsy’s moral bankruptcy, especially in his toxic relationship with young racer Little Fauss, played by Michael J. Pollard.
The film culminates in a charged confrontation:
“If this is friendship, I am aghast.”
Halsy Knox
“I never said I was your friend, Halsy. I don’t even f–king like you.”
Little Fauss
Redford later criticized the film, particularly disapproving of the director’s style, but filmmaker Alan J. Pakula, who collaborated with Redford on All the President’s Men, argued that the performance revealed an unvarnished edge in Redford’s personality:
“It was the last unself-conscious revelation of [Redford’s] real-life edge.”
Alan J. Pakula
Though widely recognized for his activism and advocacy for independent cinema through the Sundance Film Festival and Sundance Institute, Redford’s career was never without complexity or conflict beneath his polished image.
The Contrast Between Appearance and Complexity in Redford’s Roles
Sidney Pollack, another frequent collaborator, commented on the tension between Redford’s physical appeal and his deeper nature:
“Redford can play this attractive, almost metaphorical American. And when I say metaphorical American, I mean that there’s a tension that I think exists in him, and always has, between what he looks like and what he is.”
Sidney Pollack
Pollack noted audiences often underestimated Redford’s ability to portray complicated characters because of his handsome, princely appearance. He recalled struggles working with Redford on The Way We Were, where Redford resisted the role, dismissing it as
“a boring, silly reverse sex object.”
Some of Redford’s films that confronted less friendly characters or themes met with lukewarm receptions at the box office. Little Fauss and Big Halsy was a commercial disappointment and unavailable on home video for years, while Havana (1990), another film with Pollack, received muted responses despite exploring a fading gambler’s story amid the final days of Batista’s Cuba.
Redford played Jack Weil, a glamorous yet tarnished gambler drawn into a dangerous romance with Roberta Duran, the wife of a revolutionary, evoking echoes of Casablanca’s atmosphere. Pollack described the role as a departure from Redford’s usual aristocratic persona:
“I wanted to push [Redford] as far as I could, and I think he wanted to be pushed. He wanted to reach for that character. Because Redford is a kind of an aristocrat. Well, I don’t mean Redford is, I mean that’s what his image on screen is. He’s as close as we have as an American actor to an aristocrat. There’s something slightly aristocratic or privileged that one senses about him in his performances.
“But in this case, Jack Weil is anything but that. This sort of tattooed, gaudily dressed, slightly over-the-hill, little-bit-beardy guy who’s gambling all night, looking for the big sexual experience, or the big card game, or the biggest kick — that’s not the sort of character you expect of Redford.
And that’s part of the fun of it.”
Sidney Pollack
Legacy of Complexity in a Celebrated Career
Robert Redford’s career highlights reveal an actor who frequently wrestled with the gap between his public image and the darker, more troubled characters he portrayed. Though often seen as a symbol of hope, masculinity, and American ideals, Redford’s choice of roles and his work behind the camera reveal a preoccupation with themes of disillusionment, self-discovery, and moral ambiguity.
This layered approach has enriched his legacy, showing that beneath his renowned charm and activism lies a performer deeply engaged with the contradictions of life and the American experience. As he once embraced Walt Whitman’s words from Song of Myself, Redford was an individual “large” enough to contain multitudes, reflecting the tensions and complexities of the characters he brought to life.
