Marvel is a comic book company that produces and owns the intellectual properties to some of the most fascinating and compelling characters in all of fiction. Cartoons are an often-underestimated artistic medium that can convey grand esoteric concepts in a consumable, entertaining manner. Separate, these two are great things all on their own. Combined? Well, they still get their lunch eaten by DC’s cartoon line up but Marvel still has a sizable cavalcade of animated serial through which to display their storytelling prowess. Especially with Marvel’s sale to the Disney conglomerate and the unprecedented success of the MCU, the company has placed a renewed interest into their superhero cartoons.

RELATED: The 15 Most Offensive Superhero Cartoons (That You Still Love)

But no cartoon is perfect and Marvel itself has gone to some dark places in the past both in comics and films. Inevitably, a few moments of their cartoons have gone to disturbing areas of creativity, particularly for a medium aimed primarily at children. This doesn’t necessarily lessen their quality, quite the opposite in some cases, but it should be noted that as gritty as Batman: The Animated Series or Teen Titans got, Marvel was no stranger to these themes either. With that in mind, here are the 15 most disturbing episodes of Marvel cartoons.

15 "GUARDIAN ANGEL" (WOLVERINE AND THE X-MEN)

Taking a leaf out of Alan Moore’s deconstructionist playbook, Wolverine and the X-Men told the story of Wolverine reforming the team after a massive disaster so they can preemptively stop the Sentinels from creating the "Days of Future Past" storyline. It was a pretty adult series, but its most harrowing episode was “Guardian Angel.” Angel’s wings are critically damaged in a fight with the MRD and, while he’s unconscious, his father takes the opportunity to have his wings surgically removed, turning his son into a ‘proper human.’

The rest of the episode is devoted to Angel’s fall to the dark side as Mr. Sinister gives him a new set of mechanical wings, but the real kicker of the episode is the scene where Angel wakes up to learn he is distinctly no longer an angel. The tone of sheer loss and shock in his voice is nothing short of chilling.

14 "CONTROL-ALT-DELETE" (IRON MAN: ARMORED ADVENTURES)

Lots of shows have pulled a Matrix and done a hero-caught-in-illusion-has-to-break-out story, but no show has done it in such a terrifying way as Iron Man: Armored Adventures. A delightful little CGI show with a techno theme song about a teenage versions of Tony, Armored Adventures featured the episode “Control-Alt-Delete.” Tony finds himself in a weird, twisted version of his own world where none of his friends know him, nobody lives where he remembers them, and people act out of character.

Eventually, it is all revealed to be a ploy by the Controller, but the truly disturbing part of the episode is the last five seconds. After defeating the Controller, Tony marvels at the prospect of a completely immersive virtual reality and suggests the concept that all perception is merely a simulation. As he leaves to get dinner with his friends, reality glitches behind him, revealing that he’s dead right.

13 "EVERYTHING IS WONDERFUL" (AVENGERS: EARTH'S MIGHTIEST HEROES)

Avengers: Earth’s Mightiest Heroes was a contained, stylistic show that was definitively geared towards kids but was more willing to get its hands dirty than its fellow Marvel productions. Case in point, “Everything is Wonderful,” an episode-long origin story for Wonder Man. It begins in medias res before jumping to Simon Williams being shown up by Tony who buys out his company. In retaliation, Williams volunteers for an A.I.M. experiment that ionizes him and turns him into an unstable energy being.

Though powerful, his body starts to break down and dissipate. Tony tries to save him by integrating his body into a massive arc reactor, but is apparently too late. He reveals that he bought Williams’s company to help improve it, not to fold it into his own. This episode wasn’t just an exercise in introducing a generation to dramatic irony, it was a straight up Shakespearean tragedy.

12 "ULTIMATE DEADPOOL" (ULTIMATE SPIDER-MAN)

Imagine Deadpool, the merc with a mouth known for breaking the fourth wall and being as obscene as possible, on a show like Ultimate Spider-Man, a show known for breaking the fourth wall and being as puritan as a pilgrim. It goes about as nonsensically as you imagine. The episode “Ultimate Deadpool” begins with Deadpool getting eviscerated by and eviscerating a gang of thugs in a New York alley all while bombing at stand-up. And it only gets weirder from there.

Spidey joins up with him to catch the mysterious ‘Agent McGuffin’ and, when it’s revealed Deadpool was lying because of course he was, the two engage in a battle of puns, fourth wall breaks, stale jokes, weapons pulled from hammer space, and general cartoon chicanery. Also, it’s unclear if the fight takes place in the real world or in one of their imaginations. Or both of their imaginations. Maybe.

11 "ENTER, THE MAESTRO" (HULK AND THE AGENTS OF S.M.A.S.H.)

One of the weirder show concepts in Marvel’s current cartoon line-up, Hulk and the Agents of S.M.A.S.H. is mockumentary-style show about a web series made by Hulk and his gamma-powered team. It’s corny and cheesy, but gets almost inappropriately disturbing in the episode “Enter the Maestro.” Connections to the equally disturbing comic character aside, the episode is about a future version of Hulk coming back to prevent an apocalyptic catastrophe.

Once disaster is averted, it is slowly revealed that future Hulk, who calls himself Maestro, is actually evil and represents what Hulk becomes if he loses control of himself permanently. One of the most heartbreaking moments of the episode? The Hulks initially don’t trust Maestro and he says he understands why they don’t. Hulk then remarks he has a lot of experience not trusting himself. Right in the feels.

10 "THE DARK AVENGERS" (AVENGERS ASSEMBLE)

Avengers Assemble is one of the more current Marvel cartoons. Loosely based around the MCU, the show follows the mundane or, for lack of a better word, cartoonish adventures of the Avengers on a day to day basis. That also means the show can get away with more in the way of creative stories. “The Dark Avengers” sees the heroes that had been ingrained in the minds of thousands of children abruptly made into villains with almost no explanation.

In seemingly a different world, alternate versions of the Avengers are villains. A brief vision alerts evil Iron Man that something is awry and he spends the episode convincing the others that they’re supposed to be heroes. Turns out the Squadron Supreme, evil Justice League analogs, had used the reality gem to rewrite existence. But the truly disturbing part was seeing heroes be actively apathetic to the plight of innocents.

9 "BAD MOON RISING" (GUARDIANS OF THE GALAXY)

It’s safe to say that the Guardians of the Galaxy cartoon only exists because of the popularity of the movies. So it would be easy for the show to be a bland cross-promotion, and for most episodes it is. But occasionally it produces an episode like “Bad Moon Rising” to show that the clown also cries. The Guardians as they land on the moon Mandala and immediately start going crazy, reverting to their former, more psychotic personalities.

Not only does this suggest that the changes they made that define their characters are superficial and meaningless, but it’s revealed that Mandala is actually sentient (an idea James Gunn may or may not have lifted for Guardians of the Galaxy Vol. 2) and the team’s insanity is a result of a near omnipotent entity being bored and deciding to turn the heroes into its dolls. Because kids don’t need to sleep, right?

8 "MIDDLEVERSE" (X-MEN: EVOLUTION)

X-Men: Evolution was an animated attempt to bring the original vision of the X-Men, a team of teenage outcast superheroes, to the modern age. And to be fair, it did so with few, albeit noticeable, bumps in the road. One of those bumps was the episode “Middleverse,” wherein the heart and soul of the team, Nightcrawler, accidentally gets transported to a ghost dimension where he can see and hear everything that goes on in the real world, but can’t interact with it.

There, Kurt meets Forge, a tech-mutant who created the device that trapped them and had been an untouchable ghost since the '70s. That’s right, Forge basically pulled a Captain America as a teenager and, when he and Kurt escape, has 30 years to catch up on while still going through puberty. The dark implications of this are probably why Forge only had one other appearance in the series.

7 "MENTAL ORGANISM DESIGNED ONLY FOR KISSES!" (SUPER HERO SQUAD SHOW)

No Marvel cartoon show, and arguably no superhero cartoon overall, has ever pandered to kids more than the Super Hero Squad Show. Need proof? Just reread the name. The show was almost aggressively childish and tame, save for one episode that decided to explore romance, titled “Mental Organism Designed Only for Kisses!” You ever want to see Captain Marvel make out with M.O.D.O.K? It’s your lucky day!

You want to see Enchantress fail to seduce Thor and rebound onto Iron Man? Um…congrats? You want to see characters complain about how icky kissing is only to immediately round first base? You’re probably on a list somewhere. You want to see all that in a show where everyone looks like a preschooler’s action figure? Seek help, friend. Oh, and there’s a show for you.

6 "SLAVE ISLAND" (X-MEN)

The laudable ­X-Men cartoon from the '90s stands out as one of the best superhero cartoons of all time, occasionally coming near the levels achieved by the DCAU in terms of quality. And it probably couldn’t have been as good as it was without taking the odd walk on the dark side. The best example of this is probably the episode “Slave Island.” The X-Men are in the process of investigating the island of Genosha when they are captured and used as slave labor. ­

X-Men was known for its high-quality animation and its vivid depiction of mutant concentration camps and how the characters acted when presented with literally their worst nightmare was terrifyingly realistic. Storm gets locked in a box, Jubilee is confronted by jaded prisoners, and Gambit loses all hope. Things are put right by the end of the episode, but it’s hard to watch nonetheless.

5 "SNOW DAY" (ULTIMATE SPIDER-MAN)

Ultimate Spider-Man inhabits the same universe as the Guardians of the Galaxy and Avengers Assemble cartoons but with teenage leads. You’d think that would mean the show could afford to have a more light-hearted tone than its fellows, but then an episode like “Snow Day” comes along to put such thoughts to rest. Spider-Man and his team decide to take advantage of a day off and go on vacation to a tropical island.

But they soon learn they’re not alone as the island begins the change around them, isolating and gaslighting them individually. Turns out the island is the exotic prison of the Sandman, reimagined here as a bipolar, unstable tragic character. He was left on the island because his powers and mental illness made him a danger to himself and others, but solitary confinement in the middle of the ocean had only worsened his mind.

4 "SPIDER WARS CHAPTER II: FAREWELL TO SPIDER-MAN" (SPIDER-MAN)

The Spider-Man cartoon from the mid-'90s goes largely unremarked upon mostly because it wasn’t as bad as its '70s predecessor and not as good as its successors. Still, it lasted for five seasons and ended in spectacular, albeit highly disturbing fashion. The finale saw the culmination of a convoluted story involving clones, alternate worlds, and multiple symbiotes. After an alternate version of Spider-Man sacrifices himself to destroy Carnage and a team of Peter Parker's who were assembled to save the multiverse disperse.

Except the main Spidey from the series, who follows another Spider-Man who is actually just an actor who plays Spider-Man. In his world, the Spider-Man from the show gets to meet Stan Lee in one of his first recorded cameos. As a present for creating him, Spider-Man gives Lee a swing around the neighborhood before they bump into Madame Web, voiced endearingly by Lee’s late wife Joan Lee.

3 "ANTIBODY" (SILVER SURFER)

The short-lived Silver Surfer cartoon didn’t even last all of 1998 and a simple viewing of just about any episode will show why. It’s pretty terrible overall, but it wasn’t afraid to be absurdly terrifying during its brief run. The episode “Antibody” saw Surfer trying to save Galactus, despite their mutual hatred, by flying into the planet-eater’s body. In exchange for his service, Surfer is promised information on his lost homeworld. I

n Galactus’s mind, Surfer learns that his home planet is completely lost because Galactus literally threw the planet into the void of space and didn’t care to find out where it landed. Meaning that Surfer was not only ticked into saving the life of his mortal enemy, but his only hope of finding his home was virtually none. The episode ends on a hopeful note, but only through the contrivances of cartoons. The whole affair is cripplingly depressing.

2 "LIVING LEGEND" (AVENGERS: EARTH'S MIGHTIEST HEROES)

Some episodes are disturbing because of the larger implications of the story and the effects it has on the characters. Some episodes are unsettling because they suggest uncomfortable notions about humanity and our true nature. Some episodes are gross because they have a lot of gross things in them. Enter “Living Legend,” an episode of Avengers: Earth’s Mightiest Heroes.

Captain America is thawed out of the ice and realizes he’s in the future, and while that remains the main focus of the story, the B plot revolves around Arnim Zola releasing a massive goo monster on Liberty Island and Avengers Mansion. The whole blob looks like bubbling vanilla pudding that splatters across the entire screen and is genuinely kind of sickening to watch. Kudos to the animators for making something so gross it inspires real nausea, but if that feels like a backhanded compliment, it’s because it is.

1 "EMPEROR STARK" (AVENGERS: EARTH'S MIGHTIEST HEROES)

If the Netflix Jessica Jones series proved nothing else, it’s that the Purple Man is one of the most terrifying villains ever. Capable of completely controlling the actions of anyone close enough to hear him, the Purple Man’s second most jarring appearance in television was in the episode “Emperor Stark” of Avengers: Earth’s Mightiest Heroes. The episode follows the newly face Vision as he wakes up from a weeks-long repair cycle to find the world under the despotic rule of Tony Stark, being controlled by the Purple Man.

The episode is filled with the usual fights and one-liners the series was known for and leads to Vision freeing Tony from Purple Man’s control, restoring the world to its rightful place. The episode ends with Tony confessing that Purple Man hadn’t actually given him any ideas, everything he’d done had been concepts he’d legitimately produced to make his own perfect future.

Which of these episodes made you the most uncomfortable? Let us know in the comments!