Robert Redford’s screen presence made him one of Hollywood’s defining stars, but his legacy extends far beyond his performances. Through Butch Cassidy and the Sundance Kid, The Sting, Three Days of the Condor, All the President’s Men, and Quiz Show, we trace his evolution from charismatic outlaw and con man to wary investigator, determined journalist, and accomplished director. We also reflect on his transformative impact on independent cinema through the Sundance Institute and Sundance Film Festival, which helped generations of filmmakers find audiences outside the traditional studio system.