1. Paul Newman and Robert Redford
Although they’ve starred alongside each other less than anyone else on this list (twice, if you’re counting), Paul Newman and Robert Redford practically helped coin the term “buddy film.” It would be impossible to include a list of actors who have starred in multiple movies with each other without including these two legends.
The two films they starred in were Butch Cassidy and the Sundance Kid, one of the most celebrated Western films of the era, and The Sting, one of the most celebrated con films of all time. Both were directed by George Roy Hill. The Sting was nominated for 10 Oscars and won seven, including Best Picture, Best Director, and Best Original Screenplay. Redford has stated that he had planned on starring in a third film with the late Newman, A Walk in the Woods, which was released in 2015.
by Cory Barclay
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