Gene Kelly and Frank Sinatra in Anchors Aweigh (1945)

Frank Sinatra and Pamela Britton in Anchors Aweigh (1945)

Frank Sinatra and Kathryn Grayson in Anchors Aweigh (1945)

Gene Kelly, Frank Sinatra, and Kathryn Grayson in Anchors Aweigh (1945)

Gene Kelly, Frank Sinatra, Billy Gilbert, and Kathryn Grayson in Anchors Aweigh (1945)

Gene Kelly, Frank Sinatra, and Grady Sutton in Anchors Aweigh (1945)

Gene Kelly, Frank Sinatra, Jane Green, Netta Packer, Claire Whitney, and Marjorie Wood in Anchors Aweigh (1945)

Frank Sinatra, Trevor Howard, and Edward Mulhare in Von Ryan's Express (1965)

Frank Sinatra in None But the Brave (1965)

Frank Sinatra and Jill St. John in Tony Rome (1967)

Frank Sinatra and Sue Lyon in Tony Rome (1967)

Frank Sinatra in The Man with the Golden Arm (1955)

Gene Kelly, Frank Sinatra, Betty Garrett, Ann Miller, Jules Munshin, and Vera-Ellen in On the Town (1949)

Doris Day and Frank Sinatra in Young at Heart (1954)

Frank Sinatra, Janet Leigh, and Laurence Harvey in The Manchurian Candidate (1962)

Gene Kelly, Frank Sinatra, Kathryn Grayson, and José Iturbi in Anchors Aweigh (1945)

Frank Sinatra, Kim Novak, and Eleanor Parker in The Man with the Golden Arm (1955)

Marlon Brando, Frank Sinatra, Jean Simmons, and Vivian Blaine in Guys and Dolls (1955)

Frank Sinatra and Juliet Prowse in Can-Can (1960)