I am honestly tired of liking bottom of the barrel things in life and want to understand complex emotions that they show in oscar movies so my question is: How do I enjoy Oscar movies?
Oscars are shit, go
Cannes or go home
But to be less facetious, Oscars (or indeed any
awards) aren't usually signs of good films. In my experience they tend to be given to certain kinds of films. For example I fancy myself a light film buff of sorts and all of the
Sundance stuff I've seen I'd rate as horribly dull and trite. Similarly, Oscars tend to be given to certain kinds of films. If you like that sort then you'll enjoy them, but what if you don't? Ever heard of the concept of
Oscar Bait? So don't fret too much about liking esteemed films.
But if you do want to try and find "good" (for objectivity and art don't really coexist), maybe try looking at other awards than Oscars? Or perhaps try Oscars from another time? Quick googling indicated that your stuff was from late 80's and -10's. Even if you don't end up enjoying them that much, just making the cultural journey of seeing what was considered good by some in the different decades can be an enjoyable experience by itself. Check something from the 70's, 90's or maybe early 00's. What resonated with the Academy Award crowd in the wake of Cold War ending? In the wake of 9/11 and second Gulf War? Maybe that sort of observation between film and real world could interest you, maybe not.
Another option is to look for various
critics' top choices. Different critics and different institutions tend to rate things differently, odds are that 10's Oscar Institution isn't one that gels with you. Keep looking and something will probably click, but I wouldn't stress too much about it.
The way I found films that I liked, and that also tend to be highly regarded by various institutions, is I started looking into the works of directors I already enjoyed. Have you seen Full Metal Jacket or Clockwork Orange? You probably should if you haven't. If you have, well you might then be interested to know that the guy who made those also made a
bunch of other films that are similarly awesome. Think back on some of the films you enjoyed, "smart/fancy/artsy" if you insist, and then check who made them. I tend to be a pretty auteur-centric viewer, but you could concentrate on a certain director, writer, actor or whatever else. Maybe you enjoy Johnny Depp but find Pirates of the Caribbean to be low brow popcorn flick? Do consider that he's often worked with Tim Burton and while Burton has a spotty record (IMO), it includes some relatively smart films. And from Burton it's only a few google searches to other interesting/deep/pretentious films with surreal elements. That's just to offer an example of how you could find some new (or old, I recommend old, old is good) interesting films.
Key here is to find stuff that you like, not to find stuff that other people say it's ok to like (though I will add that 50 shades is pretty horrid
). Oscars isn't the only institution that tells people what to like, so don't worry if they're not the one for you.