However, there is one movie out there that I truly enjoy that I believe that I am the only person who ever watched it: Undercover Blues - 1993 - Kathleen Turner, Dennis Quaid, and Stanley Tucci.
"My name ... is Muerte!"
"Well, hi, Morty ... I'm Jeff."
Second your affection for Court Jester and To Be or Not to Be. Both well written, great acting, with clever plot twists.
Two on the list deserve higher ranking: the British dark comedy Kind Hearts and Coronets and My Man Godfrey. Both of these are worth watching again and again just for their superb acting and clever plots. In Kind Hearts, Alec Guinness convincingly plays the role of 6 different heirs to a dukedom.
I would add to the list the TV sanitized version of Idiocracy, along with A New Leaf, a small but very engaging film where Walter Matthau sets about to murder his wife for her money, as well as a number of others mentioned in this thread.
Make that 2 of us! It's one of my favorite movies. Stanley Tucci was amazing in that movie. I think Chris Tucker borrowed his scream for "The Fifth Element," which is another terrific movie, but I don't think I'd classify it as a comedy, though it was full of humor.
Mark