Here are some from my list in no particular order and mostly things I haven’t seen mentioned.
“Captain Blood,” “The Sea Hawk,” and “The Adventures of Robin Hood.” I can’t believe no one has mentioned Errol Flynn. These movies can be watched over and over and enjoyed for his performance and just good movie making.
“The Battle of Britain” A great movie about the most important battle in Europe in WWII. Americans like to think it was D-Day, but if the Brits hadn’t won the Battle of Britain, there wouldn’t have been a D-Day. This is a great movie with no CGI. Those are real WWII era planes flying all those formations and battle recreations in the sky.
“Charade.” A great suspense movie in the style of Alfred Hitchcock with two great stars the top of their game, Cary Grant and Audrey Hepburn, and a great supporting cast.
“The Day of the Jackal” Others have asked how you can rewatch a suspense movie when you know what’s going to happen. Sometimes it doesn’t matter where it goes (I mean, you know DeGaulle wasn’t assassinated), but how you get there.
“Midnight Run” Not only is Robert DeNiro a great serious actor, but he shows here he can do comedy as well. Charles Grodin and Joe Pantoliano are great supporters.
“The Maltese Falcon” Humphrey Bogart as Sam Spade. Enough said.
“North by Northwest” My favorite Hitchcock, which I probably watch every year and have for longer than I care to admit. Second favorite is “The 39 Steps,” which I’ve also watched more than 10 times.
“A League of Their Own” I don’t know why but Tom Hanks performance just knocks me out every time. It doesn’t hurt that it’s about our National Pastime, though with a new take, and that it has one of the best lines related to it: “There’s no crying in baseball!”
“Mister Smith Goes to Washington” “It’s a Wonderful Life” is a great Christmas movie, and “It Happened One Night” won all 5 top Oscars in 1935, but MSGTW is Frank Capra’s best film and one worth seeing over and over again.
Almost any Marx Brothers film, but favorites are “The Coconuts,” and “Horsefeathers.”
No Woody Allen? “Play It Again Sam” is one I’ve watched numerous times because of its inventiveness, the obvious attraction between him and Diane Keaton, and because it has some of the funniest lines in any movie I’ve seen, and I routinely quote them on any possible occasion.
“Best in Show” Anyone who’s seen it knows how funny it is even after repeated watchings. If you haven’t seen it, you should. In my opinion the funniest of Christopher Guest’s movies, but “This is Spinal Tap” is a close second.