Sorry can´t decide on one movie, I spent already to much time of my life with watching movies again, so here are some which I have seen at least 5 times:
Fight Club, Big Fish, Le Destin de Amelie Poulan, Most of the Cohen Brother Movies, The Godfather 1 + 2, Indiana Jones Triology, Star Wars from the second part on, All Kevin Smith movies, David Fincher and Tim Burton Movies such as Zodiac,Sleepy Hollow Edward Scissorhands and The Game. Most Stanley Kubric Movies, Half Baked, Cheech & Chong, Dude where is my Car (Just when Im stoned)
There are more but these are pretty much my favorites
it would have to be "White Roses for my Black sister,) Imitation of life.Overboard Goldie Hawn/kurt Russell..some many of them I never get tired of watching TCM .. to me those movies had class and decent stories lines....
Phenomenon with Kyra Sedgwick and John Travolta. I get a kick out of it. The garden scene when he manically rakes then the breeze grasps at his soul remind me of coming out of a manic episode. Works great for sharing.
The tourist - Johnny Depp, Angelina Jolie American Pie Catch me if you can - Leonardo DiCaprio, Tom Hanks The Departed - Leonardo DiCaprio, Matt Damon Inception - Leonardo DiCaprio Shutter Island - Leonardo DiCaprio
the holiday! i think it's a film that every woman can relate to. cameran diaz, kate winslet and jude law (as a single father who wears glasses and is very funny after a drink or two). it's a great film to put on if you want cheering up and i think.