The Pride and the Passion
had a troubled production, with Sinatra only taking the role to be near Ava Gardner while she shot another film, and costar Cary Grant signed on in the hopes of furthering his romance with Sophia Loren. It did boast a George Antheil soundtrack, however. To friends like Grant, Sinatra referred to The Pride and the Passion
as "the cannon movie," jokingly implying that the real star of the film was the cannon. The Joker is Wild
chronicled the life of Joe E. Lewis (played by Sinatra), a Chicago night-club entertainer who was invited to work for the Mob during the Prohibition era. Sinatra and Joe E. Lewis were, in reality, close friends. A Hole in the Head
introduced what latter became a Sinatra standard "High Hopes" to a wide audience. Both Peter Bogdanovich and Martin Scorsese have praised particular scenes in Some Came Running
and Sinatra and Dean Martin were lauded for their performances: "Sinatra gives a top performance, sardonic and compassionate, full of touches both instinctive and technical. It is not easy, either, to play a man dying of a chronic illness and do it with grace and humor, and this Martin does without faltering" (Variety).
Steve McQueen replaced Sammy Davis Jr's part in Never So Few at Sinatra's request and it was the actor's first time working with John Sturges, a relationship that would result in the classic The Great Escape.