How many movies have Hugh Hefner and James Caan acted in together?

They have worked on 3 movies together! Their first movie together was Playboy's 25th Anniversary Celebration (1979) while their highest rated movie together was Playboy Mansion Parties Uncensored (2001). They have not worked together since Playboy Mansion Parties Uncensored (2001). They are most known for their tv movie films together.