You'll notice some "great" movies missing from this list -- such as Citizen Kane -- and while there are many older movies I appreciate, I can't watch them over and over like the ten here. These are movies I have seen multiple times and that I still love to watch; I've numbered them, but they are not necessarily in order:
1. The Wizard of Oz (1939). Yes, it's cheezy and melodramatic and kitchy, but I still watch it at least once a year. A few years ago, I saw it at Cinecenta -- the first time I had watched it in a darkened theatre on a full-size screen and the tornado sequence was so much more frightening! If you've never seen it on the big screen, I highly recommend tracking it down at a repertoire theatre.
2. The Apartment (1960). This film was full of surprises for me and, while it is very dated now, it's somehow still relevant. I think this was the first Billy Wilder film I saw and certainly the first time I had seen Fred MacMurray in a darker role (I was used to seeing him on My Three Sons and in Disney films). I also finally understood why Jack Lemmon and Shirley MacLaine were stars.
3. The Day the Earth Stood Still (1951). Sure, Gort looks pretty non-threatening to today's viewers, but the brilliance in this film is the script. It's solid sci-fi and serves as a great overview of Cold War paranoia.
4. The Italian Job (1969). OK, so this was technically released the year I was born, but I'm confident that it was made before I was born and there's no way I would have seen it in the theatre. There is so much brilliance in this film -- Michael Caine is in fine form, the sequence with the Minis was brilliantly coordinated, and the ending? That's just movie gold. The "remake" from 2003 is a pathetic shadow of this movie and should be avoided at all costs.
5. The Odd Couple (1968). I never watched the TV show so I only begrudgingly bothered to watch this film the first time around. Turns out, it's hilarious and I frequently quote the characters. Full credit has to be given to Neil Simon's screenplay at the core of this film but also to the great performances by the lead and supporting cast.
6. Pillow Talk (1959). Possibly the finest example of a screwball romantic comedy with Rock Hudson and Doris Day giving some of their best performances. If you liked Down With Love, this movie is required viewing -- several scenes are almost shot-for-shot in homage; the reverse is also true!
7. The Desk Set (1957) Spencer Tracy and Katherine Hepburn spar when a computer is introduced into the fact-checking department at a newspaper. Librarians are still facing off against Google and this movie still makes me giggle for that reason.
8. Mr. Blandings Builds his Dream House (1948). Every time we consider building a house, this movie runs through my head. Cary Grant has an intense job with an ad agency and an apartment full of women so they decide to buy a house in the country. Turns out the house is falling down so they decide to build-to-suit. Despite the laughably low prices for real estate and construction and the rather offensive caricature that is Gussie, the family housekeeper, this movie is very watchable and very funny.
9. Singing in the Rain (1952). I don't consider myself a fan of musicals, but this is the second one on my list. Debbie Reynolds sparkles and Donald O'Connor cracks me up every time plus it contains some of the most recognizable Hollywood musical songs.
10. Rope (1948). Really tough call between this one and Rear Window (1954); both feature James Stewart in strong Hitchcock films but Rope is just that much darker and that much more masterful. Actually, they make a good double feature if you can handle the tension!