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20 Crazy Fan Redesigns Of Unexpected ’90s Cartoon Character Couples

For those that grew up in the era, fans consider the 1990s cartoon era to be one of the greatest of all time. Some of the great television content that came out for youths during this decade have held up very well by present-day standards. With former '90s cartoons like Power Rangers and Transformers being turned in to feature films, and animes like Pokémon and Dragon Ball still producing great content, we can see the strength of shows from this era.

The reason why these shows have held up so well over time is due to their characters . Not only were the characters developed in a way that made them entertaining for fans, but they were also given personalities that transcended the shows they were on. If the character was meant to stand for everything that was good in the world, then fans truly felt that they were the personification of good. It does not matter if it was Batman or Bobby's World, the shows made viewers feel something each episode.

That is why '90s cartoon characters work so well with fan art. Despite some of these shows not being on the air for over twenty years, fans still love the thought of these characters being a part of a relationship. There are extra bonus points given out for when these fantastic artists are able to surprise everyone with who they pair characters with. It is easy to pair characters that are "meant to be together," but to throw a monkey-wrench in and pair them with someone unexpected? That is something artistic.

Here are 20 Crazy Fan Redesigns Of Unexpected ’90s Cartoon Character Couples:

20 Poison Ivy & Two-Face

Ask any '90s cartoon fan, and they will point to Batman: The Animated Series as one of the greatest of all time. Many fingers point to how the show was able to introduce some older characters to a new audience. Especially when it came to the villains.

Imagine if they joined forces together as a couple to take Batman.

It would be hard to conquer the combination of Poison Ivy's deadly plants and Two-Face's diabolical plans. With so many diabolical villains to explore from Batman, check out the some more art from the artist here. Here's hoping that the artist explores what their children would look like, because that would be a sight to see!

19 Edna Krabappel & Bart Simpson

Ay Caramba! Who would have thought that Springfield's resident bad boy would wind up dating his former teacher? After years of tormenting her as a student at Springfield Elementary, it seems that Bart has finally toned his attitude down. He has even toned it down enough to actually catch the attention of Edna Krabappel.

She may have hated having Bart in her class for so long-- especially because he has not graduated in almost thirty years-- but seems to have come around on him later in life. The real question is - how does Principal Skinner feel about Bart dating his former girlfriend? Hopefully he doesn't have a cow! There is plenty more Simpsons artwork at Matsuri's art page, in case anyone wants to check out on their other favorite characters.

18 Beavis & Butthead

Considering that they spent all their time together on the couch, it makes sense that they would eventually get closer. Even though they do not seem to know what is going on half the time, it seems that Beavis and Butthead eventually recognized that they were sitting next to their soulmate all along.

Neither of them have also never been very successful with "scoring chicks," but hopefully time watching music videos on MTV taught them how to kiss properly.

Otherwise this is not going to be a very pleasant experience when Butthead lays his lips on Beavis. Looking for more '90s cartoon fan art? Check out the artist here.

17 Arthur & Francine

It also seems that Arthur finally started to see who was right in front of him throughout his childhood. Out of all the other characters that live in Elwood City, Francine was certainly the coolest one. Muffy is a spoiled girl, and Fern does not have a lot of self-confidence. Meanwhile, Francine's personality makes her incredibly down-to-earth. She always bonded well with the entire group, but most fandoms pointed towards her getting together with Buster later in life based on how much fun they had together.

To see a free-spirit like Francine end up with Arthur is very surprising. Hopefully these two wind up very happy together! Contributor InCaseYouArt is to thank for this (and many more) creations about television shows.

16 Wanda & Arnold

Looks like life has moved far beyond the group's time with Miss Frizzle on the Magic School Bus. While they were the polar opposites while attending Frizzle's class, it seems that Wanda has warmed up to the once very timid Arnold. Wanda was always the boldest kid in the classroom when they went on their magical adventures, and it looks like she has just gotten bolder now that she is older. Meanwhile, Arnold seems like his regular, worried self and is almost hoping that he stayed home today.

Opposites definitely attract!

Want to see some other crazy '90s art? Check out some more from muimushroom here.

15 Angelica & Chuckie

Thankfully some of the characters in these shows are able to forget some of the negative experiences from their childhood. It seems that Chuckie has fully put them behind him. In fact, it appears that he has fallen in love.

To say that Angelica was a bully to the babies in Rugrats would be an understatement. No matter where the group turned, Angelica was there in front of them to put a stop to their fun. In particular, Angelica enjoyed targeting Chuckie because he was not able to defend himself as well as the other kids.  Thankfully they have gotten past that, and made something truly beautiful.

Out of all the fantasy pairings on this list, this one is the most heart-warming.

As the artist Jose-Ramiro has included, Angelica and Chuckie have even named their child after his father.

14 Sailor Moon & Goku

What happens when a Super Saiyan and a Sailor Scout mix together? Apparently a big surprise for someone who thought they were the strongest person in the universe. Even though Goku's strength may be over 8,000 (or is it 9,000), it seems that he has found a woman capable of out-lifting him. She is the one - Sailor Moon! The Soldier of Love and Justice has taken a break from fighting the forces of evil to scoop up her potential mate, and looks incredibly pleased in doing so.

This artist has taken the two largest mainstream animes geared towards young boys and girls, and mashed them together in to the couple that no one knew they wanted. However, now that everyone has seen it, we are in love too. The only thing that SailorballGT missed from this photo is Tuxedo Mask crying in the background.

13 Wolverine & Storm

Even the strongest ones can have the softest hearts. That is what happens when adamantium meets lightning.

It is well known that the '90s version of X-Men’s Wolverine has a big crush on Jean Grey. However, it seems that he finally took the hint from Cyclops to stay away from his girl, and move on to someone much more his speed. Storm is one of the strongest mutants in the group, and likely the only one who can keep Logan in line. He may have a tendency to lash out angrily, but surely someone this strong can curb any of these feelings.

This art by dkcissner is inspired by an episode of X-Men the Animated Series, with the character designs based on X-Men Evolution.

12 Kyle & Stan

If fans look past the vulgarity, there could be the beginnings of a beautiful relationship budding in the South Park gang. While both Kyle and Stan are not nearly as vulgar as Cartman, they are certainly not suitable for children. This is why it is so nice to see a softer side of both of them.

This may be the first time that either character is seen as showing true affection for another person.

Considering that South Park has been on the air for 22 seasons, the show is now quite long in the tooth. Perhaps this couple, which artist Kite-Mitiko has dreamed up, is the answer to making the show more popular in 2018.

11 SpongeBob & Sandy

Looking for the cutest love affair you did not know existed? Look no further than stephgomz's art dedicated to Sandy Cheeks and SpongeBob Square ants.

While these two have never shown feelings for each other on the show before, fans are now wishing that would.

There may not be much reason for a burger cook and a scientist to get together, but this picture proves they there is an irresistible attraction between the two. Could a sponge who lives in a pineapple under the sea give Sandy what she needs? Will Patrick be okay with relationship? By adding in The Little Mermaid comparison, this couple got even cuter. All that is missing is Gary the Snail meowing along in the background.

10 Patti & Roger

There are two main storylines on Doug - there is Doug's love for Patti Mayonnaise, and his hatred for Roger Klotz. Throughout his entire school-life, Doug has chased after Patti and run from Roger.

That is why seeing Patti end up with his mortal enemy is surely Doug's worst fear come to life.

The artist Sallychan surely did not mean to break hearts with this photo, but every Doug fan weeps a little bit when they see this. Not even Quail-man can undo this problem in the world.

9 Raphael & April

Teenage Mutant Ninja Turtle Raphael is well-known for having the true temperament of a teenager. His mood swings have gotten him in to trouble over the years, and usually result in his brothers needing to bail him out. However, it seems that this time his emotions have worked out in his favor.

April O'Neil is one of the only humans to know about the turtle's existence. She has spent so much time with them that surely she has wondered what life would be like if they were human. In SetoAngel's fan art, she finally gets that opportunity, and it seems she is drawn to the human Raphael.

8 Daria & Tom

Did Daria and Tom get together before the end of the series? They certainly did, but that does not mean fans have not been pining for them to get back together ever since. Daria is perhaps one of the most well-known outcasts from the 1990s. Her life was never picturesque, as everyone around her never seemed to fully understand her. The only constant part about Daria's life in Lawndale is her friendship with Jane, which is what made it so surprising when she got together with Jane's ex-boyfriend Tom.

While actions like this usually turn fanbases against a character, fans instantly fell in love with the Daria-Tom relationship. When they ultimately broke up at the end of the series, it was heartbreaking for fans. Thankfully, they can live on forever in SerifeB's art projects.

7 Ren & Stimpy


Artist SkunkyNoid has managed to pair together two characters who should never have ended up together. Despite all of their years of hijinks, Ren and Stimpy have no business being in a relationship together, especially based on how Ren has treated Stimpson J. Cat over the years.

Who ever thought they would end up in a relationship?

However, if there is one theme when it comes to this list, it has to be that opposites always seem to attract. Perhaps after finally settling down when their show ended, Ren realized that Stimpy was the love he was looking for all along.

6 Heffer & Hutchinson

Want to know why the '90s were fantastic? Because it was 100% possible to dream up a relationship between a married, doctor with a hook for a hand and an over-sized buffoon of a steer.  Dr. Paula Hutchinson may be married to the emotionally taxing Filburt, but it seems that Heffer's overwhelming charm won her away. Hutch is always someone to see the good in everyone-- which fully explains her relationship with Filburt. That must also explain why she has fallen in love with someone that everyone else considers to be a fool.

While there may not be a lot of sparkling conversation, there will certainly be a lot of laughs in their relationship. Looking for some other drawings that are a hoot? Check out others from the artist here.

5 Gretchen & Vince

The best kind of love is the one that has been in front of someone the entire time-- they just did not realize it. It gets even better when that relationship stems from a childhood friendship. The Recess gang featured every type of school-yard trope that everyone remembers from elementary school. Despite their differences, Vince and Gretchen were both a part of the same group of friends. It seems that through all of those adventures on the playground, a playful relationship continued as they grew older.

Vince has realized he has feelings for Gretchen.

The artist goofymoNkey has perfectly captured their personalities, and the beginning of a very unexpected relationship.

4 Fifi Lafume & Wakko

When he is not busy running around with his brother and sister on the Warner Bros. lot, Wakko has found someone who can finally calm him down. Despite being known as the wild one of the family, Wakko seems totally at ease when staring in to Fifi Lafume's eyes. Fifi herself is no stranger to craziness, and she comes from the Tiny Toon family, who know how to get into craziness themselves.

There is something beautiful seeing these characters at peace while skating together. There is nothing loud about this relationship, just quiet bliss. VovaNinja is a fan of dreaming up plenty of cartoon couples - more of which can be seen here!

3 Dexter & Blossom

What happens when you mix a scientist with super-powered little girl? Apparently an adorably cute couple. A genius like Dexter would be enthralled with Blossom. After all, the Powerpuff Girls were created in a lab from an experiment, which is right up Dexter's alley.

Could someone who is made of "sugar, spice, and everything nice" co-exist with an evil genius?

As this fan artist explores in their drawings, sometimes opposites attract in the fantasy world. Perhaps as Dexter grew up, he became less focused on taking over the world, which is how he was able to connect with someone as sweet as Blossom.

2 Daphne & Shaggy

Any Scooby-Doo fan knows that Daphne and Fred were meant to end up together. With Fred's disposition as the alpha-male of the Scooby-Gang, and Daphne's proclivity to needing rescue, they are a natural fit together. This stereotype is exactly what makes a relationship between her and the slacker Shaggy even more entertaining.

Their personalities could not be more opposite - Daphne is a princess while Shaggy is a slacker - but these friends could be a very fun couple if they let their guard down. Besides, Shaggy does not wear a silly neckerchief like Fred, so he is instantly a cooler person. The artist Jose-Ramiro has done it again and dreamed up another great couple - have a look for some more at his page.

1 SpongeBob & Squidward

It seems that the artist Sir-Cupid has found one of the most unlikely couples in cartoon history.  SpongeBob and Squidward have a very odd relationship on their show. SpongeBob believes them to be great friends, while Squidward resents everything that SpongeBob stands for. In fact, he regularly sits and loathes all the fun and noise that comes from SpongeBob's home. Meanwhile, SpongeBob is fully oblivious to how much Squidward hates him - he just continues to go about his day happily.

Could it be that underneath all of that hatred there is actually longing and affection from the squid to the sponge?

It looks like all of Squidward's loathing is not fully gone, but that could just make their relationship even spicier!


Which of these couples do you think makes the most sense? Let us know in the comments!

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