Groundhog Day (1993)
Groundhog Day is a great movie that inspired a plethora of other surprisingly good movies that take the concept of a repeating day and do something interesting with it. But those only exist because this one is so good!
Bill Murray plays Phil who is a man trapped in an endless loop of the same day over and over again. He’s yet another character who lives life selfishly and needs to learn the importance of doing things for others so he can break the endless loop.
This is probably the most upbeat and fun movie on this list and the only straight-up comedy. Murray is great, as expected, as the day continues to repeat itself over and over. With lots of funny and recurring bits that become microcosms of the movie itself, Groundhog Day is just a ton of fun.
At risk of making the cheesiest joke of all time, this really is a movie that you could watch on repeat. It’s very nature makes it so that it won’t get old because the situations are constantly slight variations of themselves.