Pee Wee's Big Adventure
I've probably seen this movie more times than I've seen anything else. It's not so much the movie as a whole, because the plot is scattered and bizarre and even slow in some parts, but there are just moments in it, and the moments are frequent, to make this movie enjoyable over and over again.
Plus Pee-Wee's facial expressions. And the things he says. And the things he does. The hairnet when he's washing dishes in the diner. The sound he makes when he knocks over the biker gang's motorcycles. The entire basement scene... "Exhibit Q -- a scale model of the ENTIRE MALL!" The guy is just so weird. You wonder where it all comes from.