I know that everyone and their mother has attempted the "JN gang in high school!" concept...but my God, if "JN: Teen Genius" aired tomorrow, I'd be all over that shit faster than a hobo on a ham sandwich.
With that in mind, I sketched up a quick set of redesigns for the imaginary show. I'm really only happy with Libby and Sheen's, but hey, I need to move on with my life now 
So here's how I see it.
Libby
Libby may not be the most popular girl at Retroville High, but she's universally acknowledged to be the most sociable and the best-dressed. She never goes anywhere without her smart phone and ipod, and if something's going down, she's the first to know about it. While her mediocre grades give the impression of a girl uninterested in school, she is in fact a favorite among many of her teachers thanks to her extensive involvement in extracurricular activities. She's the head editor of the student gossip magazine, "Girl did WHAT?", plays five different instruments, sings solos in the choir, is a member of the school vegetarian club, and has her own blog about historical fashion faux-pas. She's planning to go to college for a media and communications degree, and hopes to eventually produce music albums and design clothes for celebrities. (I could never understand why so many fanfic writers make Libby into a total bitch in high school... I like Libby and so decided to keep her slightly gossipy, à la Lady Sings the News, but still nice).
Sheen
Sheen is that kid who's a huge nerd his whole life and then spontaneously gets hot the day he turns 18 (after all, in the good future, he does grow up to be a top male model). Libby's girlfriends have always questioned her sanity for dating him, so you can bet they're eating their words now. Sheen has taken a liking to rebellion-for-the-lulz, and his obsessive tendencies occasionally get him into trouble. He is ABYSMAL at classwork, and yet is intelligent enough to remember detailed info about every comic book and cartoon superhero show in existence. He likes wearing tight t-shirts and flirting shamelessly with the ladies, but is ultimately loyal to Libby because she's always had his back. He's got all kinds of (hidden) piercings and even a tattoo, 'cause face it, the boy likes pain. He doesn't get along well with Cindy, who is convinced that he'll drag Libby into bad decisions.
Cindy
On the surface, Cindy Vortex is the perfect straight-A student. She's goal-oriented, punctual, well-groomed, and a star athlete. She's head of the school debate team, has won multiple arts and writing competitions, and has earned every karate belt that her dojo offers. She can recite the Iliad from memory - in Greek - and she spent the summer between junior and senior year earning her pilot's license. And yet, none of her accomplishments are enough to satisfy her (I've always imagined Mrs. Vortex as a sort of caucasian Tiger Mom, and I suspect she's part of the reason for Cindy's attitude in this respect). Deep down, Cindy wants nothing more than to run away from her responsibilities and all the expectations for her future. In public, she still pretends to hate Jimmy, but in private she can barely keep her hands off him. And to make matters worse, he knows it now and loves to rub it in her face. What Cindy needs most of all is a wake-up call, because until she's honest with herself about who she is and what she wants from her life, she'll never be happy or successful. But hey, who ever figured that out in high school? 
Jimmy
Now that Jimmy's gotten better at creating inventions that actually work (you know, as opposed to causing mayhem and destruction), he's a lot more popular around Retroville. He's a star mathlete, world chess champion, and can build a hovercraft from the junk lying around in your garage. His inventions have already made life better for many people around the world, and the day he turns 21, he's gonna be stinkin' rich from all the cash waiting in his invention-sales trust fund. His naivete and desire to do good have kept this from completely going to his big fat head, but he can still be an arrogant prick sometimes. His hobbies include space travel, arguing obscure scientific theories with Cindy, and then waiting for the inevitable angry make-out session in his lab. He already has 3 college degrees, but he has secret plans to attend the same university as Cindy, just so he can waltz by and be like, "Why Cindy, you go here too? What a coincidence. Oh, what's that you say? You didn't get in early decision? Vortex, Vortex, you really should try harder..."
Carl
Senior year of high school, and our favorite redhead is still a chubber with numerous phobias and medical problems. Carl has the fashion sense of the Michelin tire man if he were living in a nursing home (it probably doesn't help that mommy still picks out his clothes for him), and most people tend to think he's pretty weird. He obviously doesn't fit in at Retroville High, but he's been able to find happiness outside of school by volunteering at the local llama farm and community garden. He's a late bloomer who tends to get along better with people outside his age group, especially really dorky old folks who wear their pants right up under their moobies. He's in a long-distance relationship with Elke, his Swedish pen pal...although nobody but Sheen and Jimmy believe that someone as odd as Carl could have such a hot girlfriend. Carl occasionally panics about his future, especially at the thought of leaving home, but Jimmy assures him that he's only a teleporter-dial away 
.........and shit, I have to get up early for work tomorrow 
WHY CAN'T I GET A LIFE 
EDIT:
Well, I caved. Mostly because Keith wanted to see Bolbi, and Em kept asking so plaintively 
So, here they are...high school aged redesigns for some of the more minor characters. From left to right: Elke Ekberg, Betty Quinlan, Bolbi Stroganovsky, Nick Dean, and Britney (click for full size).
And since I KNOW you want to waste your time reading imaginary bios:
Elke
Elke divides her time between Sweden and the U.S. During the school year, she attends her local gymnasieskola, but from June to August she works at a llama farm just outside Retroville and spends her free time hanging with Carl and his friends. Elke absolutely loves animals, especially llamas and alpacas, and she dreams of someday becoming a veterinarian. Her most prized possession is the yellow llama purse that Carl gave her during their sophomore summer - she's even been known to coordinate whole outfits around it. Elke looks forward to life after graduation, when she can move to America for college, and be closer to all the friends she's made during her visits (special thanks to Keirin-chan for inspiring me to give Elke a pixie cut).
Betty
You know, Betty gets a bad rap from fans, and I don't think it's deserved. She doesn't seem like a malicious person, and it makes no sense that people consistently write her as a maneater/seducer/conniving witch. I picture her style as mature, feminine, and classy, maybe with a 50's Hollywood flair. Since Betty's a year older than the rest of the gang, she would've already graduated by the time they hit senior year. She's super gorgeous, and all the high school AND college boys want to date her - but she's one of those chicks who "found Jesus" in high school, so now she's against teen dating and premarital shenanigans, haha. She's an active member of the local church and spends a lot of time going door-to-door bringing people "the good news" - and she has a lot more success than the less-hot members of her mission 
. Betty volunteers at the Retroville hospital as well, and she hopes to attend nursing school in a year or two.
Bolbi
THE KINGPIN, BABY 
Bolbi is tubby, bug-eyed, and incredibly bizarre...but he's found acceptance and even adoration among the members of the drama club, who respect him for his acting talents and celebrate his weirdness as "avant garde". After high school, Bolbi plans to return to Backhairistan and take over the family goat-herding business. His fashion style can best be described as "used car salesman chic", with the occasional sweater vest to spice things up. There's a bit of a rumor floating around Retroville High that Bolbi miiiight be playing for the other team, but if so, he's not out of the closet yet.
Nick
Years later, Nick is still Retroville's resident bad boy. He's cool, he's sexy, and he knows it. Now that he has his driver's license, he's upgraded from skateboards to motorcycles, and he's been in and out of trouble for skipping class to go smoke cigarettes behind the bleachers. Nick has mad skills with the ladies, and he always has at least two hotties buzzing round him at any given moment...he's even been known to charm female teachers into overlooking his tardiness and unfinished homework. Because Nick is so concerned with appearances and is so adept at coasting through life on his looks, he doesn't have any real goals set for himself after high school. It remains to be seen whether he'll be able to get his act together and move past his narcissistic loafing.
Britney
Since her appearances in the original show were mostly be limited to back-up singing for Libby and Cindy, I've surmised that Britney is one of those chicks who always seems to play second fiddle to someone else. She's known throughout Retroville High for her belly shirts, valley-girl accent, and tendency to sprinkle gratuitous "likes" into her sentences. She's a member of the cheerleading team, but despite her best efforts, has never been able to make team captain. Britney is totally devoted to Nick, but of course he's too cool to date only one girl - hopefully she'll wise up and find someone who will treat her with a bit more respect. Britney likes music, reality TV, and sports, and she hopes (perhaps unrealistically) to one day cheer for a professional football team.
Hope you like!
~*Mara*~ = ^.^ =
I will no longer be posting JIMMAY fanart in the Creative Works forum.
