Not sure if these are my absolute favorites, but these are the ones that come to mind offhand (in no particular order). Please keep in mind that I am a GIRL named Jen and as such I like some things that most fellas (including my husband) do NOT like, most specifically movies with cute smiling men who break into song and start tap dancing.
SINGIN' IN THE RAIN - Yes, it is the best musical ever made. Fills one's heart with joy from start to finish.
CASABLANCA - Bittersweet perfection. There's nothing new I can say so I won't. Gives me goosebumps.
IT HAPPENED ONE NIGHT - A hilarious Capra film that never gets old despite the fact that it's been around for almost 70 years. It's absolutely jam-packed with sweet & memorable moments. Clark Gable's dimples alone are worth the price of admission (purrrrr). Ward Bond is in this.
IT'S A WONDERFUL LIFE - Pure Capra-corn - so sweet and so wonderful. We all know that Ward Bond is in this one as well.
NOTORIOUS - My vote for best Hitchcock. Bergman & Grant are amazing together and the story really does put you on the edge of your seat. Claude Rains is one of my favorites; he is such a good actor he is able to make us feel sorry for him by the end of the film despite how terrible he is.
THE MALTESE FALCON - Classic Bogart, who maybe had as much charisma as John Wayne. Love to watch him act just with his eyes. Love Sydney Greenstreet and Elisha Cook, Jr. in this as well. And isn't Ward Bond in this one, too?
SONS OF THE DESERT - Laurel & Hardy's best feature-length film; it has the energy of all their best shorts combined with a funny and outrageous yet still plausible plotline. Too many classic moments to mention ("two peas in a pod-DUH"). I do enjoy WAY OUT WEST as well, though - especially the musical numbers.
TOP HAT - This is probably the best Astaire-Rogers musical with the score crammed full of Irving Berlin standards. It's like candy.
ON THE TOWN - Another Gene Kelly musical - fun, infectious, & brash.
SWING TIME - Another Astaire-Rogers musical that I adore. Jerome Kern score.
Some honorable mentions: AN AMERICAN IN PARIS, HOLIDAY (Hepburn & Grant), NOW VOYAGER, GONE WITH THE WIND, SHALL WE DANCE (Astaire-Rogers film with a Gershwin [*sigh*] score), anything with Gene Kelly or Fred Astaire.
I also simply adore Harold Lloyd, but would have a hard time picking a favorite film (either SAFETY LAST or THE KID BROTHER, maybe).
I guess that's good for now. I hope you guys will still respect me in the morning.