I have seen this and Holiday Inn, Blue Skies and birth of the blues. The two Christmas ones were on a other level looming for more of a comedy and musical combo. As talented as a singer Bing was he has comic chops too. Had great delivery. Looking forward to dond suggestions.
shareHow about Robin and The Seven Hoods?
shareLittle Boy Lost, 1953. It's a drama and he is so memorable in this one.
shareThe OP is looking for comic Bing and no one mentions the Road movies with Bob Hope? They (and Dorothy Lamour) made seven of these spoofs between 1940 and 1962, with the first three (Road to Singapore, Zanzibar, Morocco) from the early '40s probably being the best. They are not classic films, and even the best ones are somewhat uneven, but they are a lot of fun with some really hilarious moments. They are also surprisingly modern in many ways, since Bing and Bob break the fourth wall frequently and use a lot of in jokes (often aimed at each other and sometimes ad libbed) and running gags from film to film (the best is patty cake). As comedies go, they're not Ernst Lubitsch, Preston Sturges or Billy Wilder, but they're quite enjoyable, especially if you're a Hollywood Golden Age fan. (BTW, although they are certainly not Bing Crosby movies, Crosby also showed up in funny cameos in a number of Bob Hope comedies, notably The Princess and the Pirate and My Favorite Brunette. I recommend them.)
shareBells Of Saint Mary's is the BEST!
"Fasten your seatbelts. It's going to be a bumpy night"