My recollection is that To Be Or Not To Be is funny.
Actually, my recollection is that To Be Or Not To Be is absolutely hilarious.
But it's been quite a while since I've seen it, honestly. Not sure if my memory is accurate. (Also not sure if my memory is colored by the fact that I watched it when I was quite a bit younger and found everything much funnier).
Maybe I'm just counting on The Lubitsch Touch. There may be directors who "do satire" better than he, but there is no one who does it like he does. And this particular subject remains as ripe for satire (and for strange tonal combinations) as any.
Whatever the reason, I've loved it before and I fully expect to love it again. As soon as I get a chance to watch it on HULU (uninterrupted with PLUS; with ad if not) or FANDOR.
Set in Warsaw, Poland, during and after the German invasion of 1939, this comedy-drama mixed dedicated Nazis, ham actors, and earnest pilots and resistance fighters into a surprisingly (and, in 1942, uncomfortably) entertaining topical satire.
There's a remake with Mel Brooks streaming on AMAZON PRIME. I've never seen it, but I'm guessing it's much sillier. So, if you're looking for something along those lines, stream away.
Looking for something not quite as funny, yet still seasonally/historically appropriate? I almost recommended The Longest Day, which is streaming on NETFLIX and AMAZON PRIME. It's much less funny, really. And much longer. (Interestingly, I always find myself wanting to recommend the book, instead. Cornelius Ryan's work is extraordinary.)