Serious movies: Tarkovsky's Stalker, Andrei Rubylev, and The Mirror. Fellini's 8 1/2, Bergmans Seventh Seal, Kaufmans Adaptation, and Scorcese's The Last Temptation of Christ. I should also add The Kid by Charlie Chaplin, and Lawrence of Arabia.
Entertaining movies: Rocky I and II, The National Lampoon Vacation Movies, Planes Trains and Automobiles, DIrty Harry, Back to School, The Jerk, Great Outdoors, well most 80's comedies by Chevy Chase, Steve Martin, John Candy, Dan Akroyd, BIll Murray. There is something about seeing them countlessly in ones youth, that has made them timelessly funny for me.