Marlon Brando did not like the part of Sheriff Calder and complained that all he did in the picture was wander around. He began referring to himself as "The Old Lamplighter".
The casting director rejected Faye Dunaway, telling her she wasn't pretty enough for movies, and should stick to theater.
Producer Sam Spiegel had acquired the property on which this film was based in the 1950s and originally wanted Marlon Brando to play the role of Jason "Jake" Rogers and either Marilyn Monroe, Diana Dors or Kim Novak to play his lover, Anna Reeves. By the time production began in 1965, however, Brando was too old to play the role of the son and took the part of Sheriff Calder instead. Brando was paid $750,000 and his production company, Pennebaker, was paid a fee of $130,000. (Brando's sister Jocelyn Brando also was cast in the small role of Mrs. Briggs.)
A scene of Bubber (Robert Redford) on the run was used in the montage of escapes in Ein Gauner und Gentleman (2018), Redford's final movie before retiring.
According to Ben Mankiewicz of TCM, director Arthur Penn said about working on this film with Miriam Hopkins, "She needed a great deal of care. I have nothing but compassion for a former movie legend playing an old lady, but it takes up time."