In college, we used to do this all the time. We had a circle of friends one summer that consisted of 2-3 movie buffs, 5-6 casual movie fans, and 2-3 clueless people (never seen anything) and we put together some GREAT Triple features…
Oh, with regard to the “food” triple feature, skip My Dinner With Andre. It was Louis Malle’s biggest film mistake. I’m someone who adores “talkie-art films” (BIG Whit Stilman fan) and I HATED this film. For a good Louis Malle/Andre Gregory/Wally Shawn film, get Vanya on 42nd street. At least it had a plot. Show Mr. Nice Guy instead (Jackie Chan as a cooking show host turned asskicker).
a few suggestions based on some triple features we showed:
The Prison Features:
Shawshank Redemption, Great Escape, Escape from Alcatraz
The War Features:
Full Metal Jacket, Bridge on the River Kwai, The Battle of the Bulge
The Terry Gilliam Feature (he is a genre to himself)
Brazil, Baron Munchausen, 12 Monkeys
The Sports Features:
Field of Dreams, Slapshot, The Longest Yard
“Play on Film” features:
12 Angry Men (the original), Glengarry Glenross, Vanya on 42nd Street
Cohen Brother’s features:
Raising Arizona, Fargo, Hudsucker Proxy
Teen Angst features:
American Grafitti, Rebel Without a Cause, Kids(a truly bad movie, but even bad ones can be fun)
Also you could have some true “trilogy” triple features, like Star Wars night, “Trois Couleurs” night (for the record, though subtitled, these films are QUITE enjoyable to the American viewers), Godfather night, Monty Python night, Evil Dead night, etcetera. This is a great way to spend a day when no one has anything else to do.