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Great list...I was so pleased to see The Secret of Roan Inish included. My kids LOVED it when they were little and used to spontaneously get up and dance a jig when some of the music came on. Not sure how they knew how to jig, guess it's their Irish blood. The pace is slow and the plot kind of obscure but it still was a movie we watched over and over at their request.
Also loved "The Princess Bride" which we still quote occasionally ("Stop rhyming now, I mean it!" "Anybody want a peanut?") and Monty Python's Holy Grail, which we quote constantly ("It's only a flesh wound!" "Be quiet! I order you to be quiet!" "We have ridden since the snows of winter" "He's go two 'alves of coconuts and he's bangin 'em together!" "Help, help, I'm being repressed!" "What if we built a large wooden badger?"and on and on).
Agree with adding all Python movies and also 'Millions' which was fabulous.
Also for older kids, "Galaxy Quest" a spoof on the Star Trek genre is hilarious. My kids loved Mel Brook's "Spaceballs" which did have some funny moments along with a lot of tedious "Druish Princess" jokes. There were some sexual stuff (Brook's character talking to other character's breasts...ugh!) and language issues but they thought it was hilarious.
The Christopher Guest Canon has also been a been fun to watch as a family as the kids get older: This is Spinal Tap, A Mighty Wind, Best in Show....all hilarious.
Also, it is great to watch movies that are based, even loosely, on classics. We watched "West Side Story" when they studied Romeo and Juliet in school. We have seen some great Shakespeare (thanks to Barbara Gaines's wonderful theater in Chicago) and so have followed up "Taming of the Shrew" with Cole Porter's "Kiss me Kate" and "Ten Things I Hate About You". Same with Jane Austen's "Emma" and "Clueless". These pairings provide great opportunities for discussing social and class issues and what has changed or not changed since the originals were written. (I'm not saying "Clueless" and "Ten Things.." should make the list on their own merits, however!)
I also would echo a previous writer with regard to the R vs PG-13 issue with another example. A few years ago I took my kids (then ages 11-13) and some of their friends to see 'Anchorman' which was PG-13 and filled with jokes about sex and priapism, the latter visible in the trousers of one of the actors for a prolonged period, etc. I was not horrified, but did feel it was a bit much for a PG-13 movie. Later, I took my boys to see Farenheit 911, which was rated R and had nothing racy at all, just scary revelations about our government. It seemed that the ratings should have been reversed.