For me it's Fargo. I remember hating it when I say it 20 years ago, but after about a 10 year break I gave it another shot and can't imagine how I ever hated it in the first place. Now one of my favorite movies of all time.
For a little more context, I think when I was a younger person I found myself trying desperately to route for the characters in the film and found myself increasingly frustrated that they all seemed to make worse and worse choices until they descended into little hell's of their own making. I suppose after a decade of exposure to the real world and a fresh set of eyes, I was able to see the movie for what it is. A rather humorous farce that tells the story of terrible people reaping terrible rewards for their terrible motivations. And a damned well told story.
I think it happened because I dropped some of my own pretentiousness, to be honest. I was young, had lots of fun with the first movie, but always under the pretense of it being "philosophical", and then the sequels turned the ridiculousness to 11 โ but it's not like the first one was tame, in retrospect. I rewatched all of them after the fourth movie came out and now I really enjoy and respect the second one. The Wachowskis didn't play it safe, wore their hearts on their sleeves even harder, shot some badass and equally silly action scenes, and made a genuine story about love that I found really endearing