I saw some tweets about how he was talking to some director, and trying to get in touch with his character. The director told him to think of it like when you strike out with a girl. Redford was like "I don't know what you mean?". He'd apparently never had that experience.
I'm too "young" to have grown up when he was a big movie star but in the older movies I've seen him in he always struck me in a positive way.

Underrated movie where he's the only actor. RIP