Marvel is no stranger to the world of animation and most of its top-tier characters have been adapted to cartoon-form at some point. As far back as 1966's The Marvel Superheros, young fans have been treated to incredible adventures full of action, humor, mystery, and surprisingly enough, even moments of genuine sadness.

RELATED: 10 Animated Series Every Marvel Fan Should Watch On Disney Plus

While many modern animated shows, Marvel or otherwise, may seem to avoid serious storylines and consequences, there was a time when these things were just as important as exciting action and wacky hijinks. For many fans, the Marvel cartoons of the 90s were an especially engaging time to be a viewer, but they weren't the only ones to tug at the heartstrings.

9 Jean Grey Sacrifices Herself To Save The Universe

Jean Grey, Phoenix from 90s X-Men animated series

The 90s X-Men series was notable for many aspects, and not just the iconic theme tune. The show took time to build up its characters and storylines over multiple-episode arcs and season 3 would tackle the infamous Phoenix Saga. In "The Phoenix Saga Part 5: Child of Light," Jean Grey, now possessed by an incredible alien force, fights to save the entire universe from destruction at the hands of D'Ken Neramani and the M'Kraan Crystal.

As chaos reigns down on Earth (in a scene that includes some awesome cameos), the X-Men fight a losing battle within the Crystal. Jean and the Phoenix arrive to save them and absorb the Crystal and the villain who commands it. They realize that there's only one way to contain the powerful artifact and after an emotional goodbye to her loved ones, Jean works with the Phoenix to fly into the sun. As she goes, Cyclops and the others can only watch.

8 Spider-Man Grants The Wish Of A Dying Girl

Spider-Man from 90s animated series, Make a Wish episode

In the third season of the hit 90s Spider-Man show, a two-part adventure sees Spidey visit a young girl who's desperate to meet her hero. What begins as an innocent encounter turns deadly as Doctor Octopus attacks and Spider-Man is left with amnesia. He then winds up working WITH Doc Ock in his confusion.

The young girl, Tania, partners with a New York cab driver to try and save the day. Ultimately, they're able to help Spidey regain his memories and take on Doc Ock. As Spider-Man takes his new sidekick home, she begs him to reveal his identity. He does so, making her day and she calls him her best friend before he leaves. In the final seconds of the episode, it's revealed to the audience that Tania is in a hospice for the terminally ill.

7 Cyclops Leaves The X-Men In His Grief

Cyclops from 90s animated X-Men mourning Jean Grey

After Jean's sacrifice, the X-Men mourn her loss as a team. Scott Summers, AKA Cyclops, loses faith in his place with them and leaves. He visits the orphanage where he grew up and meets an old friend, along with the orphanage's new mutant residents.

RELATED: Marvel Animated: 5 Voice Actors Who Nailed Their Roles (& 5 Who Fell Short)

Scott comes into conflict with the villainous Zebediah Killgrave, who brainwashes mutant children to carry out his schemes. The episode did a wonderful job of highlighting Scott's character and his pain, as well as showcasing the dangers that younger mutants can experience from those who might take advantage.

6 Eddie Brock Is Deserted By The Symbiote

Venom from Spectacular Spider-Man animated series

In a more recent animated effort, The Spectacular Spider-Man saw a bold reinvention of the titular character and his enemies. Taking inspiration from the Ultimate Marvel continuity, this series saw old friends Peter Parker and Eddie Brock become bitter enemies as Brock turned into Venom.

In the episode "Identity Crisis", Venom makes every attempt to expose and then destroy the web-slinger in front of an audience, until the battle sees them within their own school. With the help of Flash Thompson, Spider-Man is able to force Venom to ingest a serum that starts degrading his symbiote. As it withers away and leaves him, Eddie begs for the creature to come back. Peter tells him to let it go and finally stop hating, but Eddie tells him that he can't and that it "only loves me for the hate."

5 Mary Jane Falls Into Another Dimension

Mary Jane falls

Back to the 90s Spider-Man and fans were treated to a rematch between Peter Parker and Norman Osborn, the Green Goblin. After discovering Spider-Man's true identity, Osborn promptly goes for Parker's loved ones and kidnaps Mary Jane Watson 

The ensuing battle takes place atop the George Washington Bridge and as the two enemies fight it out, an accident causes Mary Jane to fall into a rift created by Osborn's teleportation gear. After the Goblin's defeat, Peter is unable to find Mary Jane anywhere, and his frantic cries for her haunted viewers at the time.

4 An Early X-Men Adventure Had A Tragic Ending

Beast, Wolverine and Morph in a "Night of the Sentinels" callback in "Sanctuary"

In the opening two-parter to the 90s X-Men series, the team would be reminded of the risks they take when going into battle. "Night of the Sentinels Part 2" saw the heroes attempting to shut down the Mutant Control Agency's headquarters and prevent their deadly robots from tracking down innocent people.

RELATED: The 10 Best Crossover Episodes In The Marvel Animated Universe, Ranked According To IMDb

After managing to destroy some crucial data, the X-Men retreat from the base and are ambushed by the Sentinels. Beast is captured and imprisoned, while Wolverine's comedic friend Morph is killed in action. Despite Wolverine's protests, Cyclops orders the team to escape and leave Morph and Beast behind.

3 An Evil Version Of Spider-Man Finds Redemption

Evil Spider-Man

In the final episode of the Spider-Man animated series, the hero joins forces with various alternate versions of himself from different realities. Their aim is to stop a villainous doppelganger, a Peter Parker who bonded with the Carnage symbiote.

As their numbers dwindle and only the true Spider-Man is left to face his evil twin, he finds himself in a reality where Peter is a world-famous and cocky hero with no guilt or sense of responsibility. It's here that he discovers the greatest possible weapon against Spider-Carnage: Uncle Ben. As the distraught villain speaks with his long-lost uncle, he sees the error of his ways and chooses to sacrifice himself to save the day, and all of reality with it.

2 Beast Had To Ignore His Own Feelings

Beast from 90s Animated X-Men

Despite his appearance and codename, Hank McCoy, AKA Beast, was a kind and intelligent soul who wanted to spend his time reading and learning over fighting. In the episode "Beauty & the Beast", Hank meets a blind woman named Carly at the hospital in which he works. Carly expects to receive surgery to restore her sight, but the hospital is attacked by the anti-mutant group the Friends of Humanity due to Hank's presence.

He soon falls for her and her eyesight is returned, right before she is kidnapped by the FOH. A battle ensues and the X-Men manage to rescue Carly and deal a deadly blow to the hate group. Hank realizes that he has to let Carly go, despite his own feelings, until relations between humans and mutants can reach a peaceful stage.

1 Mary Jane Returns... Or Does She?

90s Animated Spider-Man Mary Jane Hydro

After Mary Jane falls into a dimensional rift, she miraculously reappears sometime later with no memory of where she was. She and Peter rekindle their relationship and eventually marry, and after surviving a wedding gate-crashed by the Green Goblin and other villains, finally escape to their honeymoon.

However, the trip doesn't go to plan either, as MJ's ex-boyfriend, Morris Bench/Hydro Man, ambushes them and takes her away. Peter tracks them down to a secret lab run by disgraced scientist Miles Warren, and a shocking discovery is made. Not only is Bench simply a clone of the original, now deceased Hydro Man, but Mary Jane is also a clone of the original MJ who fell into the rift. This devasting revelation isn't over yet, as MJ also displays hydro-based powers and both clones discover that they are going to degrade and die in moments. In her final seconds, she tells Peter that the real Mary Jane loves him more than anything.

NEXT: Marvel: 15 Best Animated Movies (According To IMDb)