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Great list, and a lot of good suggestions here in the Comments.
I had my son watching Keaton, Chaplin, and Lloyd from a very early age. For Chaplin, City Lights is his masterpiece but Modern Times has more to interest and delight the young ones. Keaton's best work still seems startlingly modern, and the gags kill even today. The General is probably Keaton's greatest film, and a distinct pleasure for boys. But I want to strongly recommend The Navigator as Keaton's laugh-out-loud funniest film, with a wide range of hilarious set pieces. It's the story of a spoiled, rich brat who finds himself adrift with his former girlfriend on an abandoned ship. My son (6 at the time?) was leaping up and down with laughter and excitement during the whole second half.
Others:
Zulu: Evenhanded account of an epic battle between a Zulu army and a greatly outnumbered British outpost; honors both sides and makes war look pretty grim -- but without the horrifying pornography of real war.
The Rocky formula (and that one's not bad for kids, either): Scrappy underdog works hard and triumphs in the end. Includes:
* Miracle: Kurt Russell's fine performance as coach Herb Brooks anchors this rousing tale of the U.S. Olympic Hockey Team's training for their epic 1980 battle against the U.S.S.R. Shows the value of teamwork, cooperation, and hard work.
* October Sky: Jake Gyllenhaal is Homer Hickam, son of a coal miner who decides he wants to be a rocket scientist. Inspiring introduction to the joy and adventure of science.
And a big shout out to the original Flight of the Phoenix (1965), in which Jimmy Steward & co. crash lands in the desert and depends on one of their passengers to rebuild the plane to fly them out of there. May be a little intense for younger kids.
Not So Much Department:
A Night at the Opera: I know it's considered a "classic" but it hasn't worn well. I just watched it a couple of weeks ago with my 12 year old son and he was bored through much of it. A lot of the gags are old-style vaudevillian gags incomprehensible to a youngster, or way out of date topical humor. And it's fatally schizophrenic; the anarchic Marx Brothers are all about puncturing the pretensions of the elite, but every time the two young stars break into one of their ghastly songs we're supposed to feel elevated by this Great Art. Stick with Duck Soup, but don't be surprised if it, also, fails to gain traction with modern young ones.
Mr. Hulot's Holiday: My son enjoyed it, but the pacing is pretty laconic by modern slapstick standards. Of course, Tati wasn't actually making slapstick at all, but rather laying the groundwork for his avant-garde masterpiece Playtime, an even more leisurely work but one packed with resonance. For the middle road, try Tati's Mon Oncle, which at least has conventional trappings like a modern family in a hilariously ultra-modern house.
Finally, I address the Commenter earlier (Jo Alice) who pointed out that this is a great list for educated white intellectuals, and asked for recommendations for her inner-city students. I thought of something the much-maligned Reverend Wright said on Moyers a couple of months ago: "You can't become what you haven't seen." This comment echoed something a friend told me almost twenty years ago: The Cosby Show was an eye-opener to many inner-city kids because it showed a healthy, successful black family -- one doctor, one lawyer -- in a way many black viewers had never even conceived of. It opened many eyes to the possibilities. So perhaps the best films are simply ones which model successful lives for people of color, not an easy list to compile, I'll admit. In the Heat of the Night, maybe? That's a film I loved when I was a kid. Of course, that was over 30 years ago. I don't know if it holds up as well today.
