Why didn’t I see this thread sooner?
Hmm. Just off the top of my head, I’ll go with:
Casablanca - Great cast and story; endlessly quotable
Notorious - Terrific spy drama / romance
Breaker Morant - Great as both a war movie and a courtroom drama
Star Wars: A New Hope - Thrilling, fun sf adventure
Limitless - A remarkable, clever technothriller; Bradley Cooper really should’ve won an Oscar
There. Ask me tomorrow, and it might be a different five.
Some Like it Hot
The Rose Tattoo
Treasure of the Sierra Madre
Breaker Morant
Kiss Me Kate
Darn, I wish the prompt was “Five Stupid Comedies That You Love Anyhow”… I’d just have to take some time to narrow my list from over 25 down to 5.
But, anyhow, here are My Five Movies:
Casablanca
It’s a Wonderful Life
Star Wars (no roman numeral…)
Jurassic Park
Galaxy Quest
Snatch
The Royal Tenenbaums
Unforgiven
The Big Short
Shawshank Redemption
Five perfect comedies:
Christmas Vacation
Dumb and Dumber
Planes, Trains, and Automobiles
Meet the Parents
Office Space
I’m sure most of my top five have already been mentioned, but because I left the theater thinking the same thing about The Piano, and it hasn’t been mentioned yet, I’m mentioning it.
Another five:
Dark City - Noir sf mystery/thriller set in a place where dawn never comes
Raiders of the Lost Ark - Funny, clever, breathless thrill ride
Notting Hill - Charming romcom between Hollywood mega-star and bashful bookshop owner
Pride & Prejudice - Keira Knightley at her best as the beautiful, spunky, headstrong Lizzie
Aliens - Exciting, scary, action-packed and even better than the first film
Some that I don’t think have been mentioned:
Inception
The Grand Budapest Hotel
Goodfellas
Pulp Fiction
Fight Club
Blade Runner Directors cut.
Last of the Mohicans
Out of Africa
Chariots of Fire I called it the perfect movie, superb score, true story, and very unexpectedy won Best Picture at the Oscars.
Close Encounters
The Best Years of our Lives
There are so many more… 
Zwartbroek
Turks Fruit
Trainspotting
The good, the bad and the ugly
Full metal jacket
I am modifying my list:
(If you have a date night at your place show the movie “The Commitments”…I can’t say it works every time but it has worked every time for me…not kidding, every time (yes, sex)…also legit super-great movie.)
ETA: I still think “Brazil” is fantastic but dropped it off the list since it is not easy to watch compared to the others I listed. “Brazil” is advanced movie watching…you can’t Netflix and chill that movie.
EETA: I’d also say it is the second best soundtrack to a movie ever (behind “The Blues Brothers”).
Agree about Joe vs. The Volcano. But I’m a fliberty jibit.
Tremors - a perfect genre movie.
The Maltese Falcon - like a well-crafted watch.
Jeux Interdits (Forbidden Games) - a WWII war movie that’s not really about the war.
The Taking of Pelham 123 - a movie that surprised the heck out of me when I finally saw it. Loved it.
Gosford Park - I’ve seen it at least half a dozen times, and I still see new things in it.
Damn! How did I leave that off my list??? O.k. honorable mention.
This one just missed my list.
Harold and Maude
The Big Lebowski
The Grand Budapest Hotel
Buckaroo Bonzai
My Dinner with Andre
Which version? The 1974 theatrical film, the 1998 made for TV movie, or the 2009 theatrical film?
I like:
M (Starring Peter Lorre)
Mirror Mask
Sahara (Starring Humphrey Bogart)
The Day of the Jackal (1973)
Red River (Starring John Wayne)
I like a lot of other movies too, but this was just for this particular list.
The 1974 film. Never seen the others and have no desire to.
Btw., the English title “Wings of Desire” is awful. It sounds like it’s a softcore porn movie. The original title means “The Sky over Berlin”, so why didn’t they take this?
In English, that title makes it sound like a WWII movie.
Well yes, you have a good point there I didn’t think about. What’s also lost in translation is the fact that “Himmel” means both sky and Heaven, so the heavenly aspect (it’s about angels after all) gets lost.
So maybe “Heaven over Berlin” would be best?