To Be or Not To be is probably my favorite comedy of all time. I've come to the conclusion that I need to seek out more comedies by Lubitsch, so please recommend me what you think are his best.
So far, I've been told to get "Trouble in Paradise" which is probably next on my to rent list.
You absolutely must see 'The Shop Around the Corner', which is Lubitsch at his charming, witty, hint-of-darkness best. Plus, Felix Bressart's in it again.
Trouble in Paradise is excellent, it has great comedic performances, while the plot is still interesting. I saw Ninotchka too, with Greta Garbo, which is very good too, but a little less than those other films.
"The Shop Around The Corner", which others have mentioned - it's not only Lubitsch, but has the wonderful Margaret Sullavan paired with James Stewart. I don't believe I've ever seen him more tender and gentle than he was in his films with her.
The other great Lubitsch film for me is "Ninotchka" - I'm not a huge Garbo fan, but she was perfect for this film, and backed up by a great cast, superbly directed by Lubitsch - full of sly little comic touches.
"Heaven Can Wait" tends to get lost in the shuffle, perhaps because people confuse it with "Here Comes Mr. Jordan", which was remade with Warren Beatty as, uh, "Heaven Can Wait." Anyway, the movie that I'm referring to stars Don Ameche and Gene Tierney, and belongs on the short list of Lubitsch's best films.
Design for Living isn't as good as Trouble in Paradise, but it's still really worth seeing, as is the 1934 Lubitsch version of The Merry Widow, which unfortunately isn't on DVD yet.
I love Lubitsch, but I can't understand the delight people have for "Heaven Can Wait." Yes, it has a very funny beginning, yes it's photographed well, but it just plods along and watches Don Ameche (Don Ameche!) as he lives his dull life. I don't get it.