The Princess Bride

Groundhog Day. Humor, tragedy, redemption, rodents.

Purple Rain.

If i'm having trouble sleeping or I'm stressed I'll just put that on and it'll chill me out. really relaxes me. I know it's a silly Prince movie but I absolutely love it.

it’s a tie between Hot Fuzz and Clue.

Robin Hood Men in Tights. I’m pretty much always happy to sit down and rewatch this one. Still laugh at every stupid joke.

Stardust. It's beautiful, sweet, moving, well-acted, funny, entertaining, and has a great story. Just a wonderful, comforting experience all around. One of the few movies that's decidedly better than the book.

Edit: Didn't notice that I'd been beaten to mentioning it, but it's worth repeating!

I would have to say "Drei Haselnüsse für Aschenbrödel", especially in the time around Christmas.
("Three Wishes for Cinderella", an iconic Czechoslovakian/East-German film which is pretty much total cult here in Germany.)

Apart from that (and perhaps better known internationally):
"Back to the Future" also is pretty near the top of my list.

O Brother, where art thou?

for my family it's often Back To The Future

Local Hero (1983)

Kiki's Delivery Service
Bicentennial Man

Spiderman Into the Spiderverse

Lethal Weapon

Also one of my wife's favourites so guaranted to have company :)

Tombstone

I could watch the original: Miracle on 34th St, anytime.

lotR Trilogy.

Shawshank Redemption.

There Will Be Blood.

Blues Brothers - I'm not the type of person who can rewatch movies often but I watch this at least 2-3 times a year.

Wrath of Khan directors cut.