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All Grown Up: 25 Of Our Favorite The Simpsons Characters Reimagined As Adults

The Simpsons. They’re the most iconic TV family of all time. Thinking back on the show, I’m struck by the strangeness of The Floating Timeline. That refers to the strange-yet-readily-accepted phenomenon of animated TV characters’ ages remaining static. Homer, Marge, Bart, Lisa, and even baby Maggie haven’t aged a day since the pilot episode. It’s the same deal with Family Guy or most other cartoons. In recent years, South Park has broken away from this rigid format, dipping a toe into serialized storytelling (or sometimes dunking its whole head in only to find the waters too chilling, like in season 20). But Kenny always comes back to life.

Stories require development by their very nature, which means change. But the change that occurs over the course of an animated episode is often reset next week, having little to no effect on the show as a whole. Yes, there is on occasion a Maude Flanders goodbye-type episode that becomes a permanent part of the universe’s story. But that is often the exception, not the rule. Weirdly, The Floating Timeline still works. We all instinctively understand it. They’re cartoon characters. They don’t have to age. It doesn’t have to make sense. Let me enjoy my respite from the soul-crushing slow march of aging.

Still, we can’t help imagining what the characters might be like if they grew up. It’s a question that has even fascinated the writers of The Simpsons, who have written a few flash-forward episodes. Of course, every episode has already been done because “Simpsons did it!”

25 DJ Bart And Co-Host Lovejoy

deviantart.com/the-quill-warrior

Art by: deviantart.com/the-quill-warrior

I love this piece. It tells us so much. Bart is a radio DJ in the future. Jessica Lovejoy has made a reappearance in his life. Based on his collar-grabbing and her laid-back demeanor, we have a perfect snapshot of their power dynamic.

She’s still got him wrapped around her little finger on her four-fingered hand.

The artist provides a synopsis of this spec episode. If you’re interested, click through to their page learn more.

24 Lisa’s Future Heartbreak

deviantart.com/missfuturama

Art by: deviantart.com/missfuturama

A winning entry from MissFuturama. Except this is a sad one. Thanks for making us sad, MissFuturama! For whatever reason, Lisa’s got something to cry about. We can superimpose all the causes we want but there’s no way of knowing what has her so emotional. It’s probably just a regular day of adult life. Or maybe it’s the pain of seeing loved ones go. Hey, The Simpsons are going to be thirty years old. Surely some of the elderly fan favorites haven’t survived that long. Except for Hans Moleman, who’s only thirty-one years old.

23 Who’s The Father?

deviantart.com/leif-j

Art by: deviantart.com/leif-j

Come get it, TheGamer fans. It’s a double-winner. Wonder whose kid this is? Well, the artist’s page hints at the possibility it could be Lisa’s British fiancee or even Milhouse! I’m going to officially declare that the baby is Milhouse’s because he likes spending time with the Simpsons family, unlike that cheeky Brit. Everything’s coming up, Milhouse!

22 Meet The Newest Simpson Sister

deviantart.com/leif-j

Art by: deviantart.com/leif-j

It’s a trademark of the deviantart community to include their own fan-invented characters in their favorite franchises. Allow me to introduce you to Lucy, a creation inspired by another artist. I think most of us can remember what it was like to be so in love with a show that we’d dream up new characters or even include ourselves in it, only to end up with a stack of cease and desist letters. Boy, the lawyers for Arthur sure knew how to burst a seven-year old’s bubble. Or so I’m told.

21 Big Toughies

dominicali.deviantart.com

Art by: dominicali.deviantart.com

Along with Nelson, Kearney, Jimbo, and Dolph were the meanies in Springfield. Depending on the episode, they’re either Bart’s best friend or he’s in their crosshairs. The show doesn’t seem to suggest that there’s a lot of hope in their futures. Likely they’re going to go down the same path as Otto Mann or Nelson’s mom Mrs. Muntz.

This fanart is a pretty good guess at what they’re going to look like at twenty-five. That is to say, the same.

20 Everything’s Coming Up, Milhouse

simpspin.deviantart.com

Art by: simpspin.deviantart.com

Milhouse has become Simon Sinek (he’s that guy from that TED video you might have watched one time). Throughout the series, Milhouse has tried to court Lisa in vain. This trend has even continued into flash-forwards where Milhouse got ripped to impress Lisa but to no avail.

“Why did Lisa dump me? Is it because of my small calves? They’re the hardest place to add mass!”

But here we have a switcheroo. Lisa is the one looking on regretfully at the man she rejected all those years ago.

19 Eat My Shorts And Adult Diaper

brightside.me

Okay now, this might not be what you came looking for. This is TOO old. An article title reads “reimagined as adults” — and here is a super old Bart. Being Springfield’s most notorious bad boy, Bart has made good fodder for flash-forward episodes. It’s interesting yet sad to see how our most beloved troublemaker grows up to be a functional addict with poor prospects. But The Simpsons has often been true to life *cries*.

18 A Tall Glass Of Sherri

superkoopatroopa.deviantart.com

Art by: superkoopatroopa.deviantart.com

Now is this Sherri or Terri? If you’re like the rest of us, they’re basically interchangeable— which might peeve a lot of real twins out there. I wouldn’t know. My good twin never survived. Oh my gosh, even that throwaway joke has already been done by The Simpsons (See: Treehouse of Horror VII: The Thing and I). The twins don’t get a lot of screen time on the show, but they’re recognizable enough to warrant fanart. According to the artist —and judging by her belt— this is Sherri. I’m not sure how they know either.

17 Well, This Is Awkward

deviantart.com/matsuri1128

Art by: deviantart.com/matsuri1128

This isn’t the first time we’ve seen Bart and Edna matched. As early as the third season in the episode Bart the Lover, Bart creates a fake alter ego to date his teacher. Although released in 1992, the episode foresaw cat-fishing. Cat-fishing is a terrible practice people have become more farmiliar with as the internet has marched on — needless to say, The Simpsons did it first.

16 Lisa At 30

deviantart.com/el-karpik

Art by: deviantart.com/el-karpik

Here’s a beautiful image of an older Lisa. It’s a classy, tasteful image. Not like some of the other associated images on deviantart which I beg you not to go looking for. Lisa is wearing a pink tank top with an exposed belly. It recalls the early work of a young Miss Spears. That’s fitting. If Lisa was aging realistically since the show’s release in 1989, she would come of age in the ‘00s.

15 Teen Maggie And Adult Lisa

deviantart.com/missfuturama

Art by: deviantart.com/missfuturama

Here we have adult Lisa and teen Maggie on vacation. The work is by an artist called MissFuturama, who specializes in The Simpsons fanart. I’m leaning on MissFuturama pretty hard in this article. Hey, her stuff is great. There’s not much this image tells us about Lisa and Maggie’s future. Lisa seems to be her old optimistic self while Maggie looks a tad embarrassed by her doting sister. It’s safe to assume that Lisa has gone on to great success while Maggie might be in her rebellious phase.

14 Maggie The Soldier

brightside.me

Maggie Simpson is the character on the show that people have most consistently re-imagined as older— and this time not just by fan artists. In the most famous flash-forward episode where Lisa gets engaged to that pretentious English guy, we’re treated to an older Maggie. But in a running gag, every time she opens her mouth to say something she gets interrupted. I guess we’ll never know what she really sounds like.

13 The Sun Sets On Springfield

deviantart.com/missfuturama

Art by: deviantart.com/missfuturama

Now, this is touching. Every time the writers envision a future for the Simpsons kids, Bart never gets much of a happily-ever-after. When Lisa gets to be president, he’s depicted as a good-for-nothing still getting in her away. At least this fanart shows tenderness between them in their adult years. This image has a companion fan-fiction. According to the author, “This scene took place in my story called Lisa's adventures at the Wonderplant, where Lisa was forced to work at the nuclear station under control of Mr. Burns.” I’d watch it!

12 Bart and Lisa’s Pop Stardom

deviantart.com/semiaverageartist

Art by: deviantart.com/semiaverageartist

This image is by an artist who does him/herself injustice with the username, semiaverageartist. Or perhaps they’re complimenting themselves. Either way, like all artists on this list, semiaverageartist is driven by a love of The Simpsons to the point of making their own art. I’m not totally sure why, but Bart and Lisa are pop stars? Hey, it beats most of the future depictions of Bart as a down-and-out loser so I’ll take it.

11 Barthood

imdb

Unlike the other entries in this list, this is an official still from an episode of the show. It was just too good not to include. That, and it’s hard to find solid entries for this article and why don’t you try it for a change. This is from an episode titled “Barthood” and this is the synopsis swiped straight from IMDB: A tale of Bart's journey from youth to adulthood, where he is constantly in search of approval from his father and in the shadow of his more-successful younger sister. Sound familiar?

10 Futurmama

deviantart.com/leenakill

Art by: deviantart.com/leenakill

Good news, everyone! Not only do we have an older version of Lisa, we also get a crossover extraordinaire. Lisa looks like she’s got a crush on Fry. I’m not surprised. This is rife with Freudian connotations. I mean, Fry is the closest character to what future Bart is often characterized as— a bitter burnout. Lisa may look for the same qualities in a man that she associates with her closest family members. I know, psychology is often gross. Also, I’m not good at it.

9 A Family Photo With The Newest Simpson

deviantart.com/simpspin

Art by: deviantart.com/simpspin

Another Simpsons family vacation photo. And there’s a new family member to boot! No, I’m not talking about Roy. But let’s talk about Roy. Did you know that he was a reference to FOX trying to convince The Simpsons writing staff to add a new character? I imagine they wanted to add someone like Roy, a chill young twenty-something to appeal to the coveted 18-25 demographic. Well, it worked. I want more Roy in my life.

8 Fourth Time’s The Charm

deviantart.com/simpspin

Art by: deviantart.com/simpspin

Has this article become about Eric Simpson? If you’ve glossed over all the other entries but you’re stopping at this one, allow me to re-explain. Eric Simpson is the personal creation of artist, Simpspin. Me and the other readers are cool with it because it’s neat to see one of the kids with Marge’s hair. Do keep up. Before you say it isn’t believable Marge and Homer would have another kid, allow me to remind you they already have one newborn, Maggie. They’ve just had her for thirty years.

7 Some Things Never Change

deviantart.com/yolodoze

Art by: deviantart.com/yolodoze

This terrific piece is inspired by an official episode from The Simpsons. You know the one. Lisa is going to marry that British jerk. So here we see the characters from that arc of the show continuing to have shenangians during that window. Of course Bart would take up Homer's mantle on the couch — the selfish slobs that they are.

6 Never Forget Nelsa

deviantart.com/matsuri1128

Art by: deviantart.com/matsuri1128

The Lisa and Nelson ship is an old favorite of the show. Why the connection? Because opposites attract and all that. Nelson is diametrically opposed to Lisa in almost every way. He’s an uncouth brute while she’s a bookworm.

Maybe they’re not different in any way. If I had to venture a guess as to why this ship is so successful, I think getting to see Nelson’s sensitive side is the reason.

5 Bart’s Brats

deviantart.com/simpspin

Art by: deviantart.com/simpspin

Guess whose kids these belong to? That’s right, I already said it in the title. They’re Bart’s, man. One can only hope they’re going to give him as hard of a time as he gave his parents. Now can you guess who Bart’s wife is? If the middle one didn’t give it away, it’s Gina Vendetti. Fans may remember Gina as Bart’s girlfriend from Juvie. She’s also an unlockable character in The Simpsons: Tapped Out! Huzzah! Video games! Everything comes full circle.

4 Milhouse: A Masterwork

deviantart.com/owenoak95

Art by: deviantart.com/owenoak95

This is too cool not to include. This portrait is awesome for a number of reasons; the aesthetic, the color and shadowing, the realism despite the surrealism. It’s hyper-stylized but also seems to capture Milhouse’s general persona and form in the future.

If Piccaso drew Simpsons characters, it might look something like this.

He still has an anxious and awkward outer shell even in adulthood. It’s a far cry from some other Milhouse art which depicts him as ripped and confident.

3 The Kids Made It

deviantart.com/gulliver63

Art by: deviantart.com/gulliver63

Here’s another creative reimagining of The Simpsons kids in the future. Like so many other quality works, this one also has its own fan fiction to go along with it. From the artist’s page: “Lisa's going to Springfield college, Bart takes classes on auto repair at a local community college, and Maggie is still in high school. It's cute seeing these guys never age, but it's also interesting when the show gives us glimpses of them growing up.” I know I’d watch!

2 The New Generation

deviantart.com/simpspin

Art by: deviantart.com/simpspin

Here’s a twist, folks. Notice anything remarkable about the above image? Upon first glance, we’re treated to a run-of-the-mill family photo of the Simpsons fam in the future. Not quite. Vigilant observers will, of course, note the new characters, Eric and his wife Felicia. These are creations of the artist, Simpspin. I’m not talking about them. Maggie is with Milhouse! That’s a pretty big age difference, folks. But the ship is the most surprising thing. And I’ve seen my fair share of messed-up stuff, believe me… *war flashback*.

1 Past And Future

deviantart.com/simpspin

Art by: deviantart.com/simpspin

Another fantastic fanart piece from artist Simpspin. That always means another Eric Simpson appearance. Eric Simpson is the personal creation of this fan artist. I’ve gotta hand it to the artist, it’s neat to see one of the Simpsons scions with Marge’s hair. And no, that’s not each kid lined up with their own kids. The image shows their past and future selves. Maggie’s ripped. Looks like Bart senior and Bart junior are none too impressed with each other.

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