For me, there are just four movies that I've watched multiple times and enjoyed each and every time: "Harold and Maude", "Romeo and Juliet" (Franco Zefferelli's version), "The Music Lovers" (about Tchaikovsky) and "On Golden Pond". Yeah, I know, I just revealed myself to be a bit of a buttercup. Oh, well. Pass the box of tissues, please!
Something's Gotta Give
Close Encounters of the Third Kind
ET
Any Star Wars movie
Any Lord of the Rings movie
A Christmas Story
Almost anything from the Criterion collection. Like to watch the movie, then watch it with the commentary track on, then watch it again with the knowledge.
Movies that I am happy to sit down an watch from any point if I stumble across them include: The Sting, Singin in the Rain and Music Man
Shawshank Redemption, Green Mile, Captain Philips, Steel Magnolias, Forrest Gump, A Time to Kill, The Firm, Pelican Brief, Suspect, Bridesmaids, The Hangover ("Tigers hate pepper, they love cinnamon"...) and Castaway
I am reminded by other posts how many times I have watched Simon Birch, Napoleon Dynamite and The Curious Case of Benjamin Button with my daughters over the years. And I can't forget Free Willy, Lion King, Ice Age and Finding Dory!!
Monty Python and the Holy Grail
Young Frankenstein
I have a PC full of them as well as drawer underneath the bed. Just a few that i watch over, and over again like the complete series of Lord of the rings, The Abyss, The DC films like Iron man, the complete series of Game of thrones, so many mainly Science fiction & Action films.
THE GODS MUST BE CRAZY..a botswanan film from the late seventies..
Gifted, Date Night, Dan in Real Life Night and Day, The Natural, Major League One(just a bit outside), My Cousin Vinny(you blend!)The Gods must be Crazy, Life of Brian,
Jaws, Jurassic Park, Sixth Sense, The Lion King, The Ring