In no particular order. If I had an editor, this would be more engaging.
Casablanca: you have a thing for inevitability, impossible romances and cheesy one-liners tossed about where folks are drinking.
A Streetcar Named Desire: you have a thing for inevitability, middle-age-reaching women who have a drinking problem and like teenagers; of course, you have read the play and then read it again, while watching the movie and taking notes.
Jaws: you have a thing for inevitability, "realism," mechanized sharks (and the sea); you were so inspired as a young kid seeing this on TV that you drew at least eight scenes, from memory, with Crayola on computer paper.
Amadeus: you like inevitability, thwarted genius, and costumes; the director's cut is not so bad.
Jaws II: you are an optimist who wishes she hadn't paid $10 for a sleepy sequel (also you like inevitability and you thought it would be as good as the first one).
Cabaret: you like politics, inevitability, green fingernail polish and people whose lives are colorful and tied to things Fosse-esque. You lived with one of his descendants, who was crazy but brought a lot of cable-recorded VHS tapes into your life.
Mary Poppins: you are a whole other type of optimist, who relishes voice-over singing, cardboard sets and one of the earliest attempts at live-actor+animation; you remember that some kids you babysat watched this so many times, you thought you'd explode.
Dazed and Confused: you watched this in college a few times and think it's a fun faux-nostalgic look at the America of your two-year-old youth.
The Graduate: you like watching rich LA people from the '60s be bored with the status quo, set to the soundtrack of something you listened to at least 345 times as a high schooler after you found the record (and taped it on a tape for your Walkman) at the house.
Lost in Translation: you can't get over Billy Murray movies, and this one includes not only that lovely girl but also outdated (when you were there) references to Japan.
America: World Police: you love puppets, especially the irreverent type; you respect the Sesame Street you grew up on, but this is just as good at your age.
Office Space: you like outdated scenes of drudgery that you are old enough to find humor in — a 3.5-inch floppy with a virus? Hilarious!
The Triplets of Belleville: you like animation and dark humor.
Jesus Christ Superstar: you enjoy the costumes, the sincerity and the extreme danceability of all the tracks; you sing them in your sleep; this reminds you of when you would sit in the basement, reading the booklet that came with the four-record set your mom had; even though she now votes Republican, the fact that she used to sing this, too, along with Elton John, Boy George, and the Who, provides a different kind of nostalgia.
The fact that you have no films that are any newer than 1990 (this is a guess): you also read late-18th to early 20th-century novels no fewer than 20 times each.
The majority of these movies have brought me to tears more times than I have bothered to count. (Not Office Space nor Jaws II).