1. Jacob's Ladder: Ever wanted to see Silent Hill in movie form? Well, this does that, except it actually understands its source material and puts a unique spin on it. Unlike the actual Silent Hill in movie form, which is a braindead slasher flick. Can't say much more without having a spoilers. Or Airplane. Airplane has a special place in my heart always.
2. This one's also split between Mud, The Bag Man and Ratatouille. Mud's a weird, weird coming-of-age story about Matthew Mcconaughey being Matthew Mcconaughey in a land so rural that people live on river-rafts instead of regular trailers. The Bag Man is an unapologetically flambuoyant Spy-Action-Noire thriller that takes place in a shitty motel. The whole movie looks and feels like David Lynch snorted a line of No Country For Old Men and ran off into the woods with a camera. Ratatouille is the heartwarming story of a torn-apart family finally coming together as one rat's dreams come true. Take your pick, unlike the last one, I can't tell which one of these is an acquired taste, I just know that 2/3 of them probably are.
3. Hero with Jet Li: If you're not fond of amusingly weird, hard-to-follow, Kung Fu movies, this is probably the best OG Wuxia flick you're going to find that doesn't fall into So-Bad-It's-Good territory. If we were going sheerly by my favorite Kung Fu movie, this would /easily/ be swapped out for Drunken Master (1979 original). However, sheerly because of how beautiful, layered, and epic it is, Hero probably has a lot more going for it. Noticing I may be blinded by nostalgia and the droll charms of Jackie Chan, Hero takes this spot, simply for being technically, artistically, and narratively more substantial.
4. Evil Dead 2: Takes the rules of a horror movie, turns them on their head and blatantly makes fun of them, while at the same time creating tension and even sneaking in a few genuine scares. Created the Ash we all know and love. And the gore is great too.
5. Redemption with Jason Statham: A poignant, in-depth criticism of often tonedeaf and over-romanticised aspects in action movies. It shows mental illness, the idea of a lonely drifter, the struggles of veterans, and revenge in general, for what they really are. And all without sacrificing the badass shit we watch action movies for. It's an unapologetic downer, and I love it for that. Not really the greatest as a standalone film, but it's a refreshing breath of sickening, terrible air.
EDIT: Decided to purposefully exclude Austin Powers and Indiana Jones from this list, because I can't really pick a favorite out of any of them. All I really know is that the 4th Indy (Crystal Skull) and the 4th Austin (Cat in the Hat) are both utter shit that ruined the fucking series. If I had a favorite, these would easily take 4 and 5. Hell, they'd take 2 and 3 and make the current ones 4 and 5.