Oh man.
I was nine when my parents got a beta machine and by the time I was ten, they had two VCRs and used to tape movies from rented videos and from HBO and Cinemax...this was back in 1982-3. The first movies I remember watching and re-watching endlessly were Elvis movies.
From there chronologically.....it was The Parent Trap, The Jerk, The Outsiders (this one got the most airplay--I had the dialogue memorized), The Goonies, Princess Bride (memorized), Adventures in Babysitting (memorized), Heathers (OMG, memorized, still), The Little Mermaid, Red Shoe Diaries (stole it from the video store once when I was high), and When Harry Met Sally. These are the movies I've seen at least twenty, maybe thirty times apiece since elementary school. In college, it was Heathers and all the Brat Pack movies and RSD....endlessly....over and over again night after night.
Of these movies, I've seen several of them in the past year.....okay....actually all of them except Red Shoe Diaries and Adventures in Babysitting.

And if I had them, I'd watch them this instant.
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Miles: It tastes like the back of a f*ing L.A. school bus. Now they probably didn't de-stem, hoping for some semblance of concentration, crushed it up with leaves and mice, and then wound up with this rancid tar and turpentine bull****. F*in' Raid.
Jack: Tastes pretty good to me.