With well over a million tickets sold, Bing Crosby is the third most popular actor of all time, behind only Clark Gable and John Wayne, and that's not counting the many times people have enjoyed his performances on television. "White Christmas," his most popular, with Danny Kaye, Rosemary Clooney and Vera Ellen, grossed $30 million (or over a quarter-billion in today's dollars.)
There's a lot to like about "White Christmas," not the least being the title song. Vera Ellen and Danny Kaye's dance numbers are fascinating and modern, and any chance to enjoy Rosemary Clooney's performing with Bing is worth the time. The story is a bit creaky, two Army buddies becoming a popular song and dance team and meeting up with the girls on the way to rescue their beloved general from financial troubles, but it's so warmly sentimental, by the end, you don't care.
In both his Academy Award nominated roles as wisely gentle Father O'Malley, "Going My Way" and "Bells of St. Mary's," Bing gets to play the sort of laid back character he was in real life. In the first, he is sent to reinforce a failing senior parish priest, played by Leo McCarry, to help him finish his work. The older priest suspects him to be a rival for his job, and Bing responds with convincing modesty. In his second turn as O'Malley, Bing is called on to head a Catholic school where the mostly poor children are taught and cared for by a team of nuns, headed by Ingrid Bergman. Bergman fears that his authority will undermine her freer style with children. While a side plot with a developer who wants to tear down the school develops, Bing's O'Malley is forced to manage a critical situation with Bergman without being allowed to tell her the truth.
In "The Country Daughter," Bing plays a washed up alcoholic, a role not as far off type as you might think, married to the all-sacrificing Grace Kelly, which was completely off type. For his role, he earned another Academy Award nomination. They followed that up with "High Society," Kelly's final film before leaving Hollywood to become Princess Grace of Monaco. Kelly plays an ice queen, now divorced from Crosby, who is determined to get her back before she remarries. Frank Sinatra and Celeste Holm have major roles on assignment as gossip magazine reporters, but the flavor of the film is most enhanced by Louis Armstrong who shows up with his band for jazz festival Bing is hosting. Great music and some decent comedy to go with it.
Bing Crosby made seven popular "On The Road" movies with Bob Hope, and they were planning an eighth when Bing died. But I never became of fan of those, probably because I always found Hope at least as annoying as he was funny.
Here are my favorites, in order.