Robert Redford Was Denied A Role In A Classic Film For One Very Surprising Reason

With his deep, blue eyes and dashing good looks, Robert Redford was destined to become a star. Redford started off on stage, making his name on Broadway and appearing on a number of TV shows throughout the early 1960s. He quickly rose up the ranks, earning an Emmy nomination for "The Voice of Charlie Pont" and starring in both the stage and big-screen versions of Neil Simon's "Barefoot in the Park" with the equally stunning Jane Fonda. The movie was a huge success, shooting Redford to stardom and turning him into a sex symbol. But Redford wanted to prove that he was more than just a handsome leading man and turned to his friend, director Mike Nichols, hoping to be cast in his next movie, "The Graduate." But there was just one problem: Nichols couldn't see Redford in the role.

"The Graduate" centers on Benjamin Braddock, an insecure college graduate who doesn't know what he wants to do with his life. Benjamin ends up having an affair with Mrs. Robinson, a friend of his parents, while also dating her daughter. Redford felt that if he played the disaffected youth, it would show people that he was more than just a pretty face. But his pretty face was precisely why Nichols didn't want to cast him.

Talking with Vanity Fair about making "The Graduate," Nichols recalled the conversation he had with Redford about the role. The director explained to Redford that no one would believe he was a loser, which the actor didn't believe. To prove his point, Nichols explained, "And I said, 'O.K., have you ever struck out with a girl?' and he said, 'What do you mean?' And he wasn't joking." In the end, Nichols cast the more appropriate Dustin Hoffman for the lead.

While Robert Redford didn't get to show the world that his talent matched his good looks in "The Graduate," he did find other roles to prove himself in, even if he never quite managed to play a loser. In 1969 he teamed up with Hollywood icon Paul Newman – who was also often considered too handsome for his own good — for "Butch Cassidy and the Sundance Kid," where they played outlaws on the run. While the movie doesn't present Butch and Sundance as "winners," they are undeniably cool, which keeps them from ever truly being "losers." 

In 1974, Redford tried to show the world he could play the loser, portraying one of the most iconic tragic characters in American fiction as the lead in "The Great Gatsby." The film was met with poor reviews, and Redford's take on the character was one of the larger issues for critics. Redford's best chance to show he could be the underdog was 1984's "The Natural." In the book by Bernard Malamud, Roy Hobbs is a very flawed man who throws away a promising baseball career by taking a bribe, leaving him disgraced and alone. In the film adaptation, Hobbs, played by Redford, struggles with his personal issues but, by the end, overcomes them, refusing the bribe and hitting the most legendary home run in movie history. 

Sadly, Redford died in 2025, never winning an Oscar for his acting. But he was still a winner in that area, taking home a statue for his directorial debut, "Ordinary People," proving that Mike Nichols was right when he said no one would ever see the legendary filmmaker as a loser.