Most of my picks are made with repeated watchability/listenability in mind, and with an emphasis on entertainment value over artistic merit:

Contact
Star Trek IV: The Voyage Home
Armageddon
The Natural
Secondhand Lions


Rolling Stones - Exile on Main Street
Beatles - Abbey Road
Steppenwolf - Steppenwolf Live
Neil Young - After the Gold Rush
Ron Wood - I've Got My Own Album To Do