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- Dawson Casting: One of the few complaints about the movie was that Robert Redford seemed too old to be playing a rookie character like Hooker.
- Dueling Stars Movie: It stars Paul Newman and Robert Redford. Need we say more?
- Hey, It's That Guy!: Butch and Sundance try to swindle a lot of money off of Quint.
- Playing Against Type: Paul Newman had been advised to avoid doing comedy films, because he didn't have the light touch needed to play comedy. Part of the reason Newman wanted to play Henry Gondorff was to prove that he could play comedy as well as drama.
- Reality Subtext: Robert Shaw, who plays Doyle Lonnegan, injured his knee just before the shooting began. He incorporated the resulting limp into his performance.
- Recycled Script: Much of the plot appears in the Orson Welles radio program episode of The Lives of Harry Lime entitled "Horse Play". It was on radio in 1951.
- The Red Stapler: Similarly to what Bonnie and Clyde had done for women, the film's 1930's-inspired fashions ignited a trend in men's clothes across the country with gangster suits briefly becoming all the rage.
- Revival by Commercialization: The film revived interest in Scott Joplin's music, particularly "The Entertainer".
- What Could Have Been: Jack Nicholson turned down the role of Johnny Hooker because he didn't want to do such a commercial film at the time. Warren Beatty also passed on it.
- Lee Van Cleef was considered for Henry Gondorff.
- Sterling Hayden turned down the role of Doyle Lonnegan because he didn't want to shave his beard off. Oliver Reed was offered the role, but refused to test for it. He did play the role in The Sting II. Ed Asner and Laurence Olivier were also considered.
- Henry Gondorff was originally written for an overweight, past one's prime slob, and was a minor character. He was only in about half of David S. Ward's original screenplay, and was intended to be an older, paunchier fellow-a sort of gruff mentor to Johnny Hooker. The producers originally envisioned Peter Boyle to play the role, but Paul Newman loved the screenplay and was eager to play Gondorff. Ultimately, Ward slimmed down the character and beefed up the role to fit Newman.
- The original script was a much darker tale of con men on the take. George Roy Hill envisioned it as a playful homage to old Hollywood gangster films of the 1930's.
- Written in Infirmity: During filming, Robert Redford was recovering from a broken right thumb sustained in a skiing accident a few months before, and was supposed to be wearing a cast. Numerous times in the film he uses his right hand oddly to avoid using the thumb, such as holding a fork with four fingers but not the thumb.