I was gonna say, “1999 is old?”
I was a TCM junkie for many years before Youtube and streaming were invented. I strongly prefer movies from prior to 1980, though I like some movies made between 1980 and 2000. After 2000, I have bothered with very, very few movies.
Picking favorites is going to be hard because I love so many, but I’ll give it a try.
Casablanca (yes, I know everybody loves that one but it’s just so awesome)
Quadrophenia
Diva
Seven Days in May (This was being filmed in DC when my parents were courting there, so it always reminds me of them, in addition to being a great movie. The “Judas” confrontation scene between Kirk Douglas and Burt Lancaster is my favorite.)
The Women (the 1939 George Cukor one with Norma Shearer, Rosalind Russell and Joan Crawford; I can’t believe they tried to remake it - dumb idea)
I also really love movie musicals and could list a bunch, but if I have to pick just one it would probably be
The Music Man , which I believe is the best movie musical ever made.
I also like both versions of
Auntie Mame - the original with Rosalind Russell and the later version with Lucille Ball. I probably have a slight preference for Rosalind Russell as she was my mother’s favorite actress and I can see why because my mother had a similar way of dressing and similar manner about her.
Edited to add, I forgot one.
1776. I loved it as a child and when I grew up and got it on video I went through a phase of watching it daily as I was studying for a master’s qualification exam. I got so I could quote whole sections of it verbatim.