Grace Kelly (center) poses with a cocktail in this publicity shot for the 1956 film High Society, directed by Charles Walters. Shown from left are: Bing Crosby (as C.K. Dexter-Haven), Grace Kelly (as Tracy Samantha Lord), and Frank Sinatra (as Mike Connor). High Society paired Grace Kelly romantically, and improbably, with Crosby; Kelly turned 27, and Crosby turned 53, the year the film was released. That was Hollywood logic of the era. It was Kelly's last acting appearance: the same year she married the more age-appropriate Prince Rainier III of Monaco (who was 20 years younger than Bing) and became Princess Grace of Monaco.