I'm not sure I can count how many times I've seen some movies. I'll start with those that I'm "conversational" with, meaning I could have a meaningful conversation with someone using nothing but quotes from the movie.
O Brother, Where Art Thou (DVD, my folks watched it with my kids dozens of times) - I had a counterpart that had a similar level of expertise with this, we could speak in movie quotes and no one ever knew what we were saying. Also, the gopher family scene had a special meaning. The old Chinese buffet in the last remaining portion of Lohmann's Village in Hoover had misshapened chicken planks on skewers. They browned a bit around the edges and looked a great deal like the gopher in the movie. A one word, "Gopher?", meant meet me at the Chinese buffet for a discussion.
Cool Hand Luke - An outstanding mentor of mine, quick mind, analytical and devious, at one point he and his partner were ranked number two in the world in bridge. I moved to his duty station and he rattled off a CHL quote, and I responded with the next line. Since the movie was released about the year I was born, he was taken aback, but I held my own. "It seemed like a good round number" when being questioned on a choice, "top flight police work" when stumbling across something, and so on...
Bull Durham - Probably one of my favorites in terms of usable quotes that are just obtuse enough to keep most folks at bay. I have a good friend and coworker who has been sitting with me in a room with befuddled cohorts spouting their list of thorny issues for me to unsort for them - instead of them doing the legwork of bringing solutions to a meeting - only to be met by the entire exchange of "we need to cut the head off a live...a live rooster...not breathing out of the right eyelid and no one knows what to get Millie and Jimmy for their wedding gift". We've walked out with "let's get two", and they know they need to bring more next time. The exchange in Sandy Grimes' bar is outstanding. It encapsulates the collective near misses of our world. "You get one extra flare a week, just one, a gork, a ground ball with eyes, a dying quail, you're in Yankee Stadium." It's the opposite of Fred Smith playing blackjack.
Groundhog Day - Not enough keystrokes time to discuss this one.
Various Adam Sandler and Will Ferrell movies - When my two oldest boys were in their silly years, I sat through many viewings of Happy Gilmore, Anchor Man, Stepbrothers, Mr. Deeds, Billy Madison and the ilk. I'm mildly conversational in them.
Multiple Viewings. I don't go into these situations looking to watch them. It's just a channel surf, a hesitation, and a dejected sigh from my wife, knowing that I'll be watching the remainder of the movie:
Forrest Gump
The Fugitive
Castaway
The Shawshank Redemption
Clear and Present Danger
Roadhouse (haven't seen the new one yet, but will)
Independence Day
Die Hard
Gladiator
Twister
We Were Soldiers
Apollo 13
There's a whole bunch more...