I can go on and on about movies, but I'll narrow things down to 10. In no particular order.
1. The Room. Watch it, I don't want to say anymore because that will be a filibuster. Watch it, do it. I'm not saying that because of the upcoming movie adaptation of the book that describes the behind-the-scenes story of The Room. Just watch that, you don't have to see The Disaster Artist. If you do, fucking watch the movie! Don't just one-off with the Franco film, that's my hope for said movie, it will get people to watch the grandaddy of it all.
2. A Better Tomorrow. I love this movie, so far it's my best first time movie viewing of 2017. Hong Kong action awesomeness from the 80s done by John Woo but with a very well written and heartfelt story. One I'd approve if they do an American remake. Chow Yun Fat, the fucking shit, I want to wear a trenchcoat and shades because of him. The toothpick, wouldn't fit with me though.
3. Fast Times At Ridgemont High, I don't like high school movies at all. I really don't, so the fact I recommend this says a lot. It's really funny, really well written (Cameron Crowe did the screenplay after all), memorable characters, a breeze to watch.
4. Jackie Chan's Project A. I have to recommend at least one essential Chan film, he's my number 1 in movies. Pirate stuff too, pretty light in comparison to Pirates of the Caribbean, it is a martial arts movie after all, but it's there. Really funny, crazy stunts in this, especially the clocktower sequence that Chan wanted to do 3 times, simply because he didn't like each previous take. The man dominated Hong Kong movies in the 80s, so I had to cherry pick one from that period.
5. Pulp Fiction. I'm starting to go into movies you probably have seen already, but eh. Violent, over the top, funny, dialogue that keeps you hypnotized, amazing acting, great camera work, smooth editing, a filmmaker's film basically. If that makes any sense. Fastest 2 and a half hours in your life by the way.
6. Dirty Harry. Similar to Chan, I have to recommend one Clint Eastwood movie. I would also go with The Good, The Bad, and The Ugly, but that is almost 3 hours long, so that may be a stretch. Admittedly its pace is really slow too, so I wouldn't compare it with Pulp Fiction on the speed factor. Classic movie though, no doubt about it. Dirty Harry on the other hand, pure 70s grime and grit, well polished at the same time since it's a big studio movie, Warner Bros, when they weren't sucking balls. One thing that kind of gets looked over, the villain. He's so damn good, it's not just all about Harry Callahan, it takes two to tango and that guy's so creepy, wormy, sleazy, punchable face (literally, a black man wearing gloves would agree, hint hint). I love it, the ideal 70s Hollywood movie for me.
7. Men In Black, fun sci-fi movie + Will Smith, sweet combination. I'm not that big into sci-fi movies, so I'm going with the easiest watch in the genre, and it's that film. Again you might have already seen it, but still, really fun.
8. Re-Animator. You said you liked deadpan humor. I could easily go with a Bill Murray movie, but he's too famous, I want to recommend something that should get more play. Horror movie, based on an HP Lovecraft short story, the dry humor comes from one man, who kicks Nic Cage's ass in the overacting, it's appalling that dipshit is an internet darling and not this guy, Jeffrey Combs. He plays the asshole main character Herbert West. The most lovable asshole in a horror movie though. The story is simple, someone tries to play God and it backfires multiple times, to comedic levels even, there's an infamous nude scene which I won't spoil (you probably would do it yourself if you googled the movie). Watch the "Integral Cut," the extended version, it fleshes out the story more, specifically one man's particular ability. I think the 85 minute unrated version is on Netflix, but again, I recommend the 102 or so minute version.
9. Vanilla Sky. I'm really not big on dramas, and somehow that was the first drama that came to mind. Convoluted maybe, but really interesting and lovely, and I don't know, I want to throw Tom Cruise a bone, a little love. Cameron Crowe directed this, so if you watch any of his movies and like them, you'll like this. Even Cameron Diaz, who is not a great actor, is really good in this. Also, topless Penelope Cruz, can't beat that.
10. Die Hard. Another you probably already saw, even if you did, watch for the characters. Direct your attention away from John McClane, don't focus too much on Hans Gruber even though he's amazing, focus on almost everyone else. That's what I've done since 2015 and fuck, I love the movie so much more, and I already adored it from the beginning. Given how many repeat viewings I've given it, in short spans of time no less, it has rocketed up to being in my top 10 all-time favorite movies. I'm even giddy about watching it next month, a yearly Christmas tradition. This year I appreciated the third movie in the series, Die Hard With a Vengeance, a lot more, also awesome. Die Hard 2, I love it, but it really hits on the same notes as Die Hard to a fault, and I kind of watched it too many times back in 2010 because it was TV and I DVR'ed it. So I have to give that more space in order to keep enjoying that. Die Hard 1 and 3 are different, but the former, I can watch that once a month and still love it as much as I do now. It's incredible.