How many movies have Bob Hope and Frank Sinatra acted in together?

They have worked on 7 movies together! Their first movie together was Some of Manie's Friends (1959) while their highest rated movie together was The Road to Hong Kong (1962). They have not worked together since Legendary Christmas Entertainers (2005).

Role
Chester Babcock
Role
The 'Twig' on Plutomium (uncredited)