5. Weird Science
First of all, if you're an Apple device user, especially iPad and Apple TV, you really should check out the iTunes movie store once a week or so. They're run great specials with common themes or actors, etc and discount the movies deeply from time to time. For instance, about a month ago, I found Weird Science in HD for $4.99 for one weekend in iTunes.
Weird Science exists, for me, in an emotional place that has little to do with the quality of the movie itself. There are a handful of films that I was first exposed to on HBO at my grandparents house on weekends when I'd sleep over and stay up late after they'd gone to bed. These movies were mostly over my head at the time, but they were funny, they were subversive in some way and in many cases, they were full of sex appeal.
It's no coincidence, I think that two of those movies featured Kelly Le Brock. In Weird Science, she dominated and educated two pimply teenagers, but in The Woman in Red she upended a grown Gene Wilder's life just as easily, and without the 80's computer magic.
Weird Science is notable these days for the incredibly young Robert Downey Jr playing the smirking sleazy antagonist. For me, this whole film is worth the price of admission (or the price of the iTunes purchase) just for the scene when Lisa takes the boys to the club and Gary tells his story of sadness through the lens of a cheap bottle of booze. "I was crazy insane for the woman!"
The film doesn't exactly hold up overall, but for the nostalgia and the sheer wonder that is Ms. Le Brock, this one deserves a spot on all our digital shelves.