The 2000s have been very kind to the Disney Company. The animation giant has been steadily creating amazing content for decades but the new age has allowed Disney to extend its reach to the masses. One could argue that the Disney Channel really hit its stride in the early 2000s, cranking out masterpieces like Even Stevens, Kim Possible, The Proud Family, and a variety of other popular shows.

Their success wasn’t limited to television either. Their newfound ally, Pixar, has helped them produce some of the greatest 3D animations the world has ever seen. Since 2000, Disney has graced the entertainment world with iconic films like Finding Nemo, Monsters Inc., Wall-E, The Incredibles, Cars, and many others.

To make their empire even stronger, Disney even managed to purchase and absorb the Star Wars franchise, giving them creative control over the space opera that everyone knows and loves.

But through all of these changes, Disney has stuck to their general formula of success. Each creation features a unique hero on a quest to defeat or escape a benevolent villain. Disney has tried to twist this formula a bit with recent projects but we still have an abundance of classic villains that we love to hate.

Fans are always creating new and interesting artwork to pay homage to these iconic baddies. This includes showcasing these villains as parents and with extended family. We’ve uncovered 20 pieces of family-based fan art that help to paint these villains in a completely new light. For this particular article, we are only focused on 2000s Disney villains (with one technically 90s film stuck in there!).

19 A Little Horned Bundle Of Joy

Maleficent is one of Disney’s most iconic villains. She’s been around since 1959’s Sleeping Beauty, had her own live-action film (starring Angelina Jolie), and re-appeared in 2015’s Descendants. She’s easy to identify thanks to her unique horned cowl, evil smirk, and ability to transform into a hulking green-fire breathing black dragon.

Thanks to Descendants we know that Maleficent has a teenage daughter named Mal, which led some fans to create an abundance of art featuring the evil mother and child. Precia-T shows us what Maleficent would look like as a proud new mother. There is something so adorable about seeing this evil villain taking care of such a small child.

18 A Family Scarred

We’re cheating a bit with this one but we couldn’t resist. After all, The Lion King II came out in 1998, which means that some kids who saw it (and remember it) witnessed the adventures of Simba’s Pride in the early 2000s.

In this film, we see one of Scar’s devoted followers, Zira, become the main antagonist.

There are many out there that create pictures of Scar’s “family” with Zira but Jayie-the-Hufflepuff took to it a step further and imagined Scar and Nala as King and Queen of the Pridelands, much to Nala’s disgust. We aren’t sure we like this Simba-less alternate future.

17 Raising Her Own Villainous Prodigy

Kim Possible tangled with a lot of villains during her time as a cartoon crimefighter. She found herself constantly saving the world from the likes of Monkey Fist, Warmonga, Gill, and a slew of other baddies. Yet, the abundance of villains aside, perhaps her biggest arch enemy was Dr. Drakken. He and his henchwoman Shego were a serious thorn in Kim Possible’s side.

Shego was especially troublesome, thanks to her strength and intelligence. She would clash with Kim on numerous occasions and push the secret agent to her absolute limit. Thanks to her “dedication to the craft” we can imagine that Shego would love if her daughter followed in her evil footsteps.

Source: rinacat.

16 Frozen Hearts Find One Another

While we’re on the subject of terrible villains that we all love to hate, we might as well talk about the handsome manipulator, Hans. Frozen attempted to break the Disney mold, showing children everywhere that it’s not exactly proper to instantaneously trust and fall head-over-heels for someone you just met.

Hans served as the perfect example for this important lesson. The man had been conning Anna from the start and planned to put an end to Elsa. But artist PrincessOfCorona imagines what it might be like if Hans and Elsa fell in love instead and started their own family, complete with an ice-infused child.

15 Oh Captain, My Captain

With each successful Disney animated featured film, we saw the introduction of new iconic villains, each with their own unique desires and attitudes.

In 1953, Disney wowed audiences with their rendition of Peter Pan, the story of a young boy who never grows up.

Kids and parents alike were captivated by Peter, the world of Neverland, The Lost Boys, and the frightening antagonist, Captain Hook. We know this article pertains to 2000s Disney villains, but a technicality allows us to showcase Hook here with his two children. Descendants (2015) is a recent film that follows the children of a variety of Disney villains.

Source: y-yuki.

14 A Family From The Other Side

The process of shipping characters seems simple from the outside but there are many people who are dedicated to the craft, showcasing just how complex it can be to weave multiple stories and universes together.

No characters are off limits when it comes to shipping. This includes the massive roster of Disney villains.

Artist CancerSyndromEdits gives us a glimpse at what it might be like if two of Disney’s crazier villains decided to play fathers to an adorable daughter. Everyone knows how firey Hercules’ Hades can be and after watching The Princess and the Frog we all know just how devilishly evil Dr. Facilier really is.

13 No Dogs Allowed

Like Maleficent, Cruella de Vil has made waves throughout the Disney universe and has appeared in a variety of different shows and films. Her first appearance was in 1961’s 101 Dalmatians and again in 1996’s 101 Dalmations remake. She can also be seen (with a son, Carlos) on 2015’s Descendants and is even a popular character on the Once Upon a Time series.

This particular piece of fan art shows Cruella starting a family with “the Author” from Once Upon a Time, with the two having an adorable son and daughter. Hopefully, the duo doesn’t plan to get a dog anytime soon, Cruella doesn’t have the best track record with animals.

Source: AnnettaSassi

12 We Still Despise Her!

Every so often, Disney comes up with a villain that far exceeds our evil expectations. Most villains do terrible things to get what they want but a few Disney baddies go above and beyond when it comes to achieving their wicked desires. Mother Gothel is a prime example and someone that Tangled fans absolutely love to hate.

Not only is she a twisted and deceiving woman, but she outright stole a child and successfully wasted a quarter of her life by keeping her imprisoned in a tower. All of this was done to give her a youthful appearance. This fan art imagines the wicked woman as a caring mother to Rapunzel but it doesn’t make us hate her any less.

Source: SerifeB.

11 Ewe’ll Love This Family

Plot twists can be mind-blowing and impressive when done correctly. Disney has generally stuck to its roots when it comes to developing clear-cut villains with dastardly motives. Zootopia changed things up quite a bit, offering up a cute and cuddly villain that viewers would be sure to remember for years to come.

In the beginning, Bellwether looked like a mild-mannered, adorable, sheepish secretary. As the film progressed, we found out that she was actually the mastermind behind all of the predator-based happenings throughout Zootopia. If she’d become a mom before the events of the film, perhaps things would have turned out much happier for the assistant turned antagonist.

Source: MustLoveFrogs.

10 Racing Through The Snow

Wreck-It Ralph resonated with a lot of us, thanks to its mixture of Disney magic and video game references. We loved the character cameos, as well as the main themes and interesting way that storytellers introduced to us the worlds inside of our favorite games.

It’s always fun to imagine what our favorite heroes and villains are doing whenever we are not actively playing through their adventures.

Wreck-It Ralph was another film that featured a secret antagonist, with viewers finding out that King Candy was really the malicious villain Turbo, who was seeking revenge after losing the “best game” spotlight. Perhaps if Turbo spent more time with Vanellope, he wouldn’t have minded living happily in the world of Sugar Rush.

Source: Kittykatpaws

9 So Much In Common

We already took a look at what Shego from Kim Possible might look like as a mother but this creation from Dinogaby showcases the parental side of Drakken too. There are many fans out there that believe that Shego and Drakken belong together, and it’s hard to argue when you witness the playful love/hate chemistry between the two. When it comes to villain-based ships, this is definitely one of the most popular.

It would be really interesting to see if these two would change after becoming parents. Drakken seems like the type of villain that would try to groom his children to become villains themselves but Shego might want to simply settle down.

8 He Created A Family-Inator

A lot of the entries on this list feature villains in fictional family settings. Many of the baddies you see never had children of their own but that doesn’t mean Disney hasn’t blessed a few evil-doers with their own kids. One 2000s-era Disney dad is Dr. Doofenshmirtz from the popular series Phineas and Ferb.

The bumbling evil scientist is constantly working on his array of Tri-State-area-conquering inventions but he still found time to create his own bundle of joy. It’s canon that Doofenshmirtz has a teenage daughter named Vanessa and this creation from Cezille07 shows an adorable moment between father and child when she was much younger.

7 An Incredible Dad

The Incredibles is easily one of Disney-Pixar’s greatest creations. The superhero adventure is the perfect blend of family fun and high octane action. It took the studio far too long to develop a sequel (according to fans) but the wait was well worth it with the recently released Incredibles 2 dominating the box office.

In homage to its current success, we thought we’d revisit the villain from the first film, Syndrome. The powerful villain put the Incredible family through the ringer, proving to be a very formidable foe. Artist crumblygumbly imagines what the maniacal madman might look like as a father. It seems that the parental role has completely changed the villain, reforming him into something heroic, rather than villainous.

6 The Ultimate Racing Team

We already showcased Turbo in a fatherly role as King Candy but it would be interesting to see how things would go for him if he changed his ways after revealing himself to the gaming world. Perhaps all it would take for Turbo to “turn good” is for the villain to finally have something other than super-stardom to strive for.

Perhaps that thing would be having a daughter of his own.

This creation from the appropriately named Turbotastique has the villain-turned-parent showing Vanellope his original game. He’s still as sarcastic, snarky, and proud as ever. It’s good to know that even if his alignment changes, his personality won’t.

5 The Absolute Worst Inlaws

People generally cringe when it’s time to meet the family of their significant other. Some of the greatest relationship dramas and compatibility tests can arise when family gatherings are involved. Some families just don’t get along with one another and there are many instances in which a significant other finds themselves shunned by the parents and siblings of their loved one.

PSI-missing imagines what this might be like by meshing two Disney families together that are sure to despise one another. This fanart sees the daughter of Kim and Ron falling in love with the son of Shego and Drakken. Talk about family drama.

4 The Next Scourge Of The Galaxy

Every once in a while a Disney film or animated series comes along that surprises and captivates us. There are many that argue that Disney has lost its luster since the early 90s but there are still some animated gems to be found. Take, for example, the wonderfully wacky series, Wander Over Yonder. Unfortunately, the intergalactic adventure only saw two seasons. It was still a wild ride from start to finish.

From the beginning, Wander found himself clashing obliviously with Lord Hater but later on in the series, a new threat named Lord Dominator (who was actually female) was introduced. In this case, we see Wander looking at Lord Hater as a father rather than a rival.

Source: DawkwingSnark.

3 Ohana Means Family

Lilo and Stitch was nothing short of a pleasant surprise when it premiered in 2002. There was something so fascinating about the “escaped alien experiments” storyline and Stitch was just adorable. Unfortunately, Stitch’s cuteness did little to distract the villainous Captain Gantu from arriving in Hawaii to bring the little creature into custody.

In true Disney villain fashion, Gantu is eventually thwarted and forced to admit defeat at the hands of our heroes.

That hasn’t stopped some fan artists from imagining the giant Galatic Federation soldier as part of Lilo and Stitch’s ohana. Maybe all the villain really needed a was a family of his own.

Source: ErinPrimette.

2 A Spooky Good Looking Family

Monsters Inc. featured a ton of creepy, crawly, and monstrous creatures. The premise for the film was imaginative, showcasing a world in which monsters live by scaring children. The central plot revolved around the loveable Sully and hilarious Mike as the duo discovered a rotten plan to force children into powering the world in which they live.

At the center of this terrible scheme was Randall, a slimy lizard-like creature who was always creating problems for Mike and Sully. Thanks to DoorToTheOtherWorlds we know what it might look like if Randall abandoned his evil ways and settled down with his own family.

1 It’ll Have The Best Uncles

We know this list is all about villains and while Dr. Doofenshmirtz is definitely the “main” antagonist of the Phineas and Ferb series, you can definitely make an argument that Candace is a villain. No, she’s not interested in dominating the Tri-State area, but she’s definitely a “bad guy” when it comes to her brothers.

Candace is constantly trying to bust Phineas and Ferb and plans to promptly put an end to each of their daily schemes, no matter what she has to do. That makes her a villain in our eyes (especially since we love the inventive brothers so much).

Leave it up to Phineas to make an astute (yet humiliating) observation about his pregnant sibling.

Source: Fruttistdar