Clueless’s Josh is a college nerd. He cares about the environment, social issues, and geopolitical foreign policy. He reads Friedrich Nietzsche for fun, and he’s the step-brother of Cher.
It’s been 25 years since the film came out, so if he doesn’t really seem like a total geek, rest assured, next to a fashionista and supermodel hopeful played by Alicia Silverstone, he is a bonafide dork. In real life, clearly, he’s drop-dead gorgeous. Oh, and did we mention he co-owns a New York candy store with actor Jeffrey Dean Morgan? You don’t need us to tell you that candy is cool, do you?
Alfonso Ribeiro – The Fresh Prince of Bel-Air
Standing next to Will Smith, anyone is going to look like a dork. The Fresh Prince’s cousin Carlton Banks is signed, sealed, and delivered as far as dorkiness goes. And not to mention the fact that Carlton is responsible for one of the nerdiest dances in the history of TV.
He is also annoying, arrogant, awkward, and known to flaunt a superiority complex to a comical effect. The television star is still on TV. Alfonso Ribeiro hosts "America’s Funniest Home Videos." This means his job is to talk about funny internet videos. That may very well be the coolest job on the planet.
Ariel Winter – Modern Family
"Modern Family's" Alex Dunphy is smart, sarcastic, and snarky. Her intelligence causes her to be impatient with her family, who she considers dumb as dirt. She’s the middle child who feels like an outsider and would be glad not to be related to them. Certainly, she was one of the breakout stars of the popular sitcom.
In real life, Ariel Winter is all grown up and not afraid of wearing clothes that accentuate it no matter the criticism. When faced with some of her haters' comments, she told them to simply “get a hobby.” Only cool kids can say it like it is, and she's definitely one of them.
Mara Wilson - Matilda
We are met with Roald Dahl’s Matilda in kindergarten. The lovable child genius is played by Mara Wilson In the 1996 film version. Her character has a despicable dad who lords over the Wormwood household, and she deals with him with an ironclad anti-intellectual bent.
Wilson has since quit acting and turned to professional writing. She has even published a couple of books: "Sheeple" and "Where Am I Now?: True Stories of Girlhood and Accidental Fame." Definitely cool. Oddly enough, she doesn’t consider herself exceptionally attractive. She even tweeted “Hot people’s lives are WILD. Their Instagrams alone. They don’t even have to try.” Somehow, this makes her even cooler.
Alexa Vega – Spy Kids
In "Spy Kids," Carmen Cortez transforms into an international secret agent to save her parents, who are real secret spies but have gotten into a bit of a bind. She’s cute and funny and has a pesky baby brother.
In real life, Alexa PenaVega is a beautiful, happy mother of two, raising her family in Hawaii with her husband Carlos PenaVega. Vega's talents stretch beyond acting and reach the realms of singing and dancing. She has contributed her voice to the soundtracks of many of the films she starred in and came in sixth in season 21 of "Dancing With the Stars." That's pretty darn cool if you ask us.