Everything Everywhere All at Once, Interstellar, Fight Club, Arrival, The Sixth Sense, Primer. I'm sure I could go on but all of those are great on a rewatch.
All three of those make much more sense the second time around.
In general, though, that's a matter of personal preference. I will never turn down Young Frankenstein, The Blues Brothers, Blazing Saddles, Groundhog Day, or The Princess Bride.
Primer or really any good time travel movie. For Primer, you pretty much have to re-watch out to make sense of what is going on. Highly recommended though!
Ramayanam
Mahabharatam
Unforgiven
The magnificent seven
The good, bad and the ugly
There will be blood
Nuvvu naaku nachaav
Athadu
Cloud Atlas
Cast away
Bahubali
Deyyam
......
Maybe not worth rewatching every night/weekend, but from time to time I absolutely love rewatching Legend of Hei.
I don't remember where, but I remember some people online kinda comparing it as something like a Chinese Studio Ghibli film, which in a way is partially true since it has a magical feel to it.
I got a DVD/Blueray set through Shout! Factory and do not regret the purchase, personally.
Margin Call, The Big Short, The Wolf of Wallstreet, Nobody, Moneyball, The gentlemen, Layercake, Heat, The Running Man, Roadhouse.
BTW, if you've not heard of it, The Rewatchables is a great podcast where a group of guys talk about and critic movies they consider rewatchables. If you're interested, listen to episode 1. The list of shows would be a pretty good answer to your question but this list is off the top of my head.
my personal favorite is Kiki's Delivery Service, as it's a film that doesn't have common Disney/Western tropes of trauma or horrible things happening. the main character has a loving family, she is strong willed, sticks to her convictions and is honest/empathetic/kind. there's action and conflict in a non violent way and the characters are sane. while I don't have kids, it's also appropriate for children and has lessons that are valuable for all ages.
the animation is beautiful to boot and the story is fun. I honestly think it's an example of a perfect film.
i've only seen reservoir dogs once but i feel like i need to rewatch it just to gain greater understanding of the whole situation. those are my favourite type of rewatch experiences.