Media I Like (that you should like, too)
Movies
I cannot overstate how much I recommend everyone see Knives Out. SUCH a good movie 
the characters feel dynamic and interesting, the plot keeps you on your toes, and it has such a whimsical vibe despite the heavy topics and it knows when to cut the shit and get real for impact, too. Every time I watch it, I see something new to be impressed by lol. The sequel, Glass Onion, is also good, not better than the first imo, but still very good.
Red Lights is also a spectacular movie. It didn't get great reviews or ratings, but that's not because it's a bad movie. There's a lot of context to know going in, and the target audience is pretty niche. Before you watch it, learn about James Randi, a very respectable man who put a lot of effort into exposing and debunking fake healers and psychics. Learn about the fake healers and fake psychics, and the way they scam people en masse. 
How they tell sick and desperate people that they'll fix all their problems, if they just keep paying large amounts of money that leaves them in debt, stringing them along with false hope and lies. That context matters. Check out the James Randi videos in this playlist (or the whole thing). I haven't watched this through, yet, but this video goes into the topic as well
Also Longlegs is a movie that keeps giving. Every time you watch it, there's more to see. There's so much to decode, to piece together, little details here and there to leave you wondering. And an ARG to go with it. The intent behind the film is so interesting as well, the director (Osgood Perkins) grew up with a gay or bi father during a time where you didn't talk about that. His father, Anthony Perkins, was the star of the movie Psycho, and died of aides-related illness at 60. Knowing the context of queerness, illness, repression, trauma and the impact these things had on Osgood's life going in really color the experience!
A little less in-depth with these lol... I also recommend Pan's Labyrinth, which I would describe as a serious-toned, darker Coraline, which I also recommend. Treasure Planet, Ratatouille, the OG Mulan and Tangled. The first How to Train your Dragon, and unironically Shrek 1 & 2. Plus, if you're 30 give or take a few years, grew up in the US, you should watch the entire lgbt+ movie series, Eating Out. You'll see a lot of familiar things in it and it was a serious throwback into highschool for me (even though I think they "take place in college").
Comics
Of comics and webcomics, Homestuck is one with such cultural/internet significance that you're really missing a lot of history if you don't take a look 
Is it long? Yeah.
Is there a plethora of lore, intent and inside jokes to uncover? Yeah!
So if you like deep-dives, you can see homestuck and all the necessary (and unecessary) reading right here, learn some history here, and you can look around to dig up some behind the scenes stuff as well.
Anya's Ghost 
is a graphic novel with interesting characters and an interesting story, and a really soft, pleasant art style that tells the story well. If you were/are a moody teen
or if you didn't fit in well, if you were out of place in the place you grew up or are growing up, it will speak to you.
Games
So, JRPGs... Misao and Mad Father by the creator Sen. They're nice stories with a lot of personality and lore packed into them, and Misao in particular takes on a tone I find similar to Corpse Party, which I also suggest checking out. And then basically any of JRPGs by Uri, with some of my personal picks being Mermaid Swamp, and the full Strange Man series- The Crooked Man, The Sandman, The Boogie Man, and The Hanged Man. These are all horror, and all really interesting little stories with mysterious to uncover and puzzles to solve.
A different kind of JRPG, play Breath of Fire 3 for PS1. If you don't have a PS1, or over a hundred dollars to spare on a discontinued game franchise, well- you could probably look around and find something in a place like this that would help you achieve your goal, but I wouldn't know about that! 
It's a cute little game that follows a cute little guy named Ryu
his purple-haired friend Teepo, and their neko gaurdian-ish, Rei. The game played with gameplay mechanics that were new at the time, giving a twist to the traditional JRPG. Super good, super cute game
One of my favorite games growing up was The Cat Lady, which at the time looked like a standalone game but is actually part of series. I've only experienced The Cat Lady and part of the following game, Lorelai 
but I'm sure they're all just as good. It deals with heavy themes, like depression, suicide, murder, and basically everything else. But the way it handled depression really struck a cord with me. Without spoiling too much, you play as a woman who attempted suicide. Afterwards, at home, you're just trying to avoid a mental breakdown. Mess up making coffee? One step closer to a breakdown. Find a stresser while you're looking for something you need? Closer to a breakdown.
The world knows about Undertale by now, which makes my list of "everyone should play" 
but there's certainly some inspiration taken from a less popular game. I was just in time to see the peak of the fandom, and it has pretty much faded into obscurity by now. OFF is a really cool game that plays with morals, ambiguity, and tells a story through metaphors (or something). It deserves more attention, although I'm not really 100% sure you can actually play it anymore...
It might be lost to time by now. Both games are good, but Undertale gives you a choice, and OFF tells a story.
Cartoons
You'll notice by this list that I'm really into cartoons... lol. These aren't all kid's cartoons, so please be mindful of the content before going in if you're sensitive to anything!
If you like artsy, silly, random humor (often with a darker atmsophere), check out Grim Adventures of Billy and Mandy, Invader Zim, the OG Powerpuff Girls, and Misadventures of Flapjack. Maybe Chowder, too. They're all cartoons you can really feel the creativity in 
with stylized art and awesome color usage, even if they're not really your thing.
The OG Powerpuff Girls follows three lab-created little girls while they learn normal lessons with OP superpowers
Flapjack is about a boy who lives with his adopted whale-mom and reluctant father-figure, and Chowder is about a boy apprentice in a weird food-oriented world. There's also... Foster's Home for Imaginary Friends, which seems mostly forgotten these days but is so, soooo good. About a world where imaginary friends become real upon being imagined, and the fact that kids don't keep them forever.
Then you haaave Regular Show which (barely!) pretends it isn't about stoners slacking off and partying whenever they get a chance, and Adventure Time, which... has so much lore. So much. And Gravity Falls, which has mysteries, thrills, believable and loveable characters, and then some extra lore and extras in books and short clips. Some more artsy, creative shows with a lighter tone are Edd Ed and Eddy, which follows three boys named with variations of "Ed" around their neighborhood. Hi Hi Puffy Ami Yumi 
which is a show about the singers of the Teen Titans theme song. Rugrats, which is about 4, 5 and then 6 babies and two older kids and their wacky hijinks. I never watched it, but people really liked My Little Pony: Friendship is Magic when it was airing.
If you prefer superhero stuff, the OG Teen Titans 
Young Justice, Invincible, the OG Ben 10 and Danny Phantom. They're all pretty standard teenagers-with-super-powers up until Danny Phantom
which has a more unique take on it. Although you'll find better characterizing and worldbuilding in the fandom than the show, thanks to a certain guy who has a name that rhymes with Futch Bartman. (And probably less humiliation kink, too- BH is a weird guy). If you're into similar things but craving more fantasy, Avatar: the Last Airbender is probably perfect.
For shows more geared towards adults, I'm currently very into Common Side Effects, an amazing and thought-provoking shows about a magic, healing mushroom. By the same creator, Mike Judge, there's also King of the Hill, a pretty wholesome show about a conservative Republican family in Texas, and The Goode Family, which centers around a liberal, hippy family in California. They're genuinely all so good. But if you're looking for something to brain-numbingly 420 to, there's Smiling Friends, which has a lot of background gags, chronically online humor and references and stuff, or Mr. Pickles, which has SO MUCH GORE but is about a demonic dog who is also just a dog. And Aqua Teen Hunger Force, which is about fries, soda and hamburger living on earth, and their neighbor, Carl. These are NOT child-friendly shows at all lol.
More non-kid shows, South Park, although if you're not old you probably will be lost in the earlier seasons for references and at-the-time current events. Still a good show, but keep in mind that it's one of those shows where the fanbase misses the obvious messages and takes it as a "yeah, shit on people I don't like!" lol. Speaking of, Rick and Morty has similar notoriety in terms of the fanbase, but is a good and funny show anyways. A lot of people didn't like when it started having more of a plot, but I personally enjoy it a lot more now.
Television Shows
If you like mystery, creepy stuff and slow-burns, X-Files is great, and Supernatural is a close second. If you lean towards horror, Hannibal is good, but much darker, and same for Dexter. Hannibal is a bit more serious and arsty, and Dexter feels more sterile and clinical. Prison Break was a goofy show with a cool plot and cool characters, if you suspend your disbelief you'll like it a lot more lol. I'd recommend Sherlock and Doctor Who starting in 2005 in the same tier. Not like, a masterpiece, but they both had a big following for a reason. Breaking Bad is really good, heavy though for something starring Malcom's silly dad from Malcom in the Middle, which I also recommend! It's a much lighter comedy that shows a realistic view of a poor/lower middle-class family. That dynamic is lost these days with the shrinking middle class and all lol...
For lighter, stupid-funny shows or just nostalgic vibes, I used to really like That's so Raven, Hannah Montanna, Lizzy McGuire, and Glee. And, although I think they're a bit bad or problematic in retrospect, Secret Life of an American Teenager and Prety Little Liars both held my heart at one point in time/
Other Stuff
Also, I'm working on building up collections of all the anime I've seen, and recommend and the games I've played/seen playthroughs of and recommend. But it's such a WIP, because I forget everything I've ever experienced the moment I try to think about it.