Redford played a very deceitful dirt bike-driving cad in Little Fauss and Big Halsy (1970). Halsy is a role he especially disliked and it's the last time he portrayed such a character since he shortly after went on to major stardom and got the power to pick only roles to his liking.
As a matter of fact, many of his earlier roles are scumbags. Check out his appearances on Alfred Hitchcock Presents and The Alfred Hitchcock Hour in which he plays a variety of scoundrels and murderers. He also portrays a very despicably selfish character in Inside Daisy Clover (1965). All those are roles Redford was admittedly uncomfortable playing but had to as he was still a beginner yet to make his name back then.
I'm here, Mr. Man, I cannot tell no lie and I'll be right here till the day I die
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