• Monty Python’s Holy Grail, Life of Brian and Meaning of life (in that order of rewaches). Although I haven’t seen them in years, now that I live somewhere where weed is legal I should do that (never seen them stoned)
• Primer, which if it’s not on your list here you either haven’t seen it or haven’t understood it
• The Mummy and Harry Potter (especially the first couple). They’re one of my wife’s comfort movies so we watch them every once in a while if she’s feeling down
• LotR, although it’s more of an event to rewatch them.
• Stargate, every few years we rewatch the TV show when we have nothing else to watch, we do that with some other TV shows as well as it’s good background noise to just relax. And since it starts and ends with movies we’ve watched those several times.
• Pink Floyd’s The Wall and Daft Punk’s Interstella 5555 are awesome music albums so I have watched those several times
• Hair, similarly love the musics

And although I haven’t seen them too many times (but at least twice) Memento is a great movie if you haven’t seen it. Also I haven’t seen it multiple times but The Strangers is a great horror movie.