Disney's Aladdin is pretty racist in that ”if you steal, we'll cut off your hand” depiction of Middle Eastern society, and it never questions whether having a monarch who lives in a massive palace and forces his daughter to get married is actually bad.
Plus, when Aladdin becomes Prince Ali, the song says he has slaves 
This is a weird one but the nihilism of Robot Chicken used to really get to me. Just vignettes of characters dying horrible ironic deaths. Its funny I guess in a group setting but alone and stoned in my room, not so much. I think the elephant in the room is South Park. Especially around 2013/14 when they helped bring the term "PC" back into the political zeitgeist, which was the buzz word the right loved before "woke".
Soooooo much shit I enjoyed as a kid had a plot where a dude 'wins' a woman as a prize for completing the hero's journey, and I genuinely think it messed up the entire millennial generation
1980s GI Joe is the most glaring example I can instantly think of.
I am still baffled by the fact that decades later some blue curtain bazinga in my guild in one of the games I played insisted that the good old days of cartoons had zero political messaging, unlike today, and his example was... GI Joe.
After I gave exhaustive examples of the political messaging of that show (everything from the plain as day glorification of the US military, the OPEC oil crisis being simplified as being backed and perpetuated by a bunch of terror-loving puppet governments... puppets of Cobra of course) and what I got back was, verbatim, "did anyone ever tell you... the curtains are fucking blue?" 
It's a low bar, but all the copaganda shows (CSI, Castle, Brooklyn 99, Bones, etc) for obvious reasons. Even the heckin' wholesome funny NYPD detectives in B99 talk about defense lawyers being scum, all suspects being guilty (otherwise they wouldn't be suspects, would they?) and of course even when they did touch on the rampant racism in the NYPD the solution was "be a better pig and change from the inside!" (Don't laugh!). I could go on about the others too, but it's a topic that's already been covered better by other people
Long post short, even light-hearted cop shows where Malcolm Reynolds plays a goofy man-child writer have dogshit politics
Rikki-Tikki-Tavi, which takes place in colonial India, and is about a mongoose defending a white settler family against evil indigenous cobras. The mongoose kills all 3 snakes and squashes the mother cobra's eggs, then a bird sings about how that is good actually, and all the snakes never dare enter the white colonist family's garden again, the end
Looking back, with the political education I've had, a case could be made that Paw Patrol contains some subtle pro-police messaging. Can't be too sure tho.
Stickdeath.com, although I was already a teenager at that point. Stuff like ”Crackhouse Clean-Up” where the bad guy green stickmen were obviously supposed to be black stereotypes, but back then I didn't know enough about 
racial politics to realize.
After 9/11, the guy started doing cartoons of racist Middle Eastern caricatures being killed by US soldiers while Korn played and racist caricatures being tortured in Gitmo, and the fucked up messaging was no longer hidden 
The first Ace Ventura movie is unwatchably transphobic now. 
As a kid I thought the United States of America was the best in the world. Hell I pledged allegiance to the flag nearly every day.
Turns out its just a racist fascist shithole run by and for corporations.
Finding out that the author of Death Note's absolute dogshit way of writing women wasn't just the usual shonen author bullshit and fanservice but he's actually a big misgynist chud who writes women badly on purpose.
Worst one is I thought Jeff Dunham was hilarious up until I was like 10. Glad I was done with that before middle school lol
Donalc Duck. It has a status where I live, it "teaches kids to read". One of our brainwormed metal music artists who is a fan even did the whole "woke-mind virus" outrage in the media after it was suggested we remove the most obviously racist and colonial images from it.
Tbh I have noticed and known how problematic it is from the start, as a girl reading the way women are framed in these comics was eternally annoying to me as a kid. So was the way it Others anyone who isn't Western.
But it took me longer to notice how incredibly white it is, how it frames people who do crime and how Scrooge McDuck is a settler colonialist image that worships billionaireism/getting rich. Pretty sure most of my age group also were in a Scrooge McDuck Club where the comic would send you tips on making money, saving money and essentially idolizing the figure by making sure we think he got that rich by wit, by being smart with his money and by courage alone.
Another offshoot of this here is the Italian versions of it where the incredible meanness and kind of violent framing of life always bothered me a lot as a kid, the way Donald got put into basically slave labor for lols and such.
I read it on the toilet sometimes still, mostly to re-educate myself on the framing in it. Just the other day read a story with Mickey Mouse and the Goofy Indiana Jones where language like "the savages" is just casually used. It has been an effective tool for Othering here for sure.
The comic was brought to this country by a right-wing capitalist and framed as project to get the kids to read. I get it now.
Redwall. Such a fun book series, but when you think about it, it strongly endorses something that pretty neatly maps to racial essentialism (the "bad" species, e.g. rats, stoats, ferrets, etc, are portrayed as inevitably irredeemable, even when raised by "good" creatures).
Tintin. It took me until I read "tintin in the Congo" to realise something was up. It really hit a second time when I found out Hergé was Belgian.
Then of course the whole cowboy stuff that was sooooo popular. Karl May, Lucky Luke etc.
Even a lot of lullabies or play songs are so plainly racist its mindboggling. I was worried about having to check what media my kid is consuming when he gets older what with all the copaganda and other korra-like liberal messaging but the overt racism in songs for babies really blindsided me.
And then others look at us like "why are white people so racist?" My friend, we've been fed this shit before we could even understand speech.
007 spy shit, along with stuff like Mission Impossible and MacGyver being used to romanticize US imperialism and anti-communism.
There's also Tomb Raider's Lara Croft engaging in plunder of other nation's indigenous artifacts and outright killing delicate, endangered wildlife.
There's also the trend of rock, metal, and various other similar type bands showcasing nazi and white supremacist symbolism and rhetoric (Pantera's lead singer comes to mind) (from nazi salutes to iron crosses (Lemmy's guitar from Motorhead had these on them), to brown shirts and nazbol flags (Combichrist), to more subtle dogwhistles), stuff like confederate flags (Combichrist), and a few instances of members turning out to be perpetrators of SA (Tool's lead singer), and even things like vulgar misogyny and anti-LGBTQ+ themes (also Combichrist).
There's a lot of insidious far-right influences in a lot of shit, and it's quite sad.
As a kid I played a game called Secret Weapons of the Luftwaffe, a flight sim by LucasArts designed by the guy who would later do X-Wing and TIE Fighter (I guess the latter was also bad because you fought with the space fascists). You could fly all kinds of Nazi planes that never saw action in real life like jet fighters, and it wasn't until much later whenI realized that glorifying cool Nazi superweapons was bad, actually.
Same with Panzer General, which was a fun lite strategy game otherwise, but you literally played as Nazi Germany. I can't believe that actually wasn't considered a big deal at the time.
All cartoons, which are for babies. They have the fucked message that they're not for babies.
Upon introspeecetion, I didn't like that Goku spared Freiza. Goku was clearly told by Vegeta that Freiza's a genocidal space tyrant responsible for annihilating the Saiyans, Goku believed Vegeta, but spared Frieza anyway. Because Frieza put up a good fight or was pathetically groveling.
Also the Saiyans inhibiting Bulma from finding Gero & The Androids/Cell before they were supposed to show up. The TeamFourStar joke about Piccolo being more of a father to Gohan rings really true.
For me though:
Attack on Titan, but during Season 1/2.
Eren's "kill or be killed" mantra was a red flag. Then the government being controlled by a secret leader/conspiracy stuff. Whole series was a fascist dog siren.
Noted fantasy writer Piers Anthony
Didn't really notice the misogyny or leering at underage girls at the time
Also his writing is just garbage even ignoring the problematic content
1984 used to be my favourite book as a child 💀
I was a huge NCIS fan in my early 20s. Realized looking back that's it's just a big patriotic circlejerk
Pepe le Pew. I haven't watched it since I was a kid but thinking back he'd mad stalker/rapey vibes
I absolutely love the movie hackers but it has a surprisingly homophobic/transphobic scene considering how queer coded many of the main characters are. Maybe to appease the censors. It was the 90s after all.
It also packs a lot of patriarchy and misogyny despite also making Acid Burn the most bad-ass character.
Bleach. Well I still like the new Bleach as well
Author inserts Nazi imagery and parallels for apologia everywhere. Average anime lmao
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