Ronald Miller was a dorky, unpopular high school kid who rode a lawnmower for a part-time job. His problem was that he fell in love with wealthy, popular cheerleader Cindy Mancini, who he bribes for a date.
It’s a silly rom-com, but sweet—the exact typecast we have grown to expect from Patrick Dempsey. But Dempsey has sure come a long way since then and has been the man every TV viewer wants to either be or be with, having starred in “Grey’s Anatomy” as the beloved “McDreamy.” In 2014, the man out-cooled himself when he debuted his second career as a professional race car driver.
Felicia Day – Supernatural
It’s no surprise IT nerd-turned-hunter Charlie Bradbury is a "Supernatural" fandom favorite. Introduced as the “Girl with the Dungeon and Dragons Tattoo,” Charlie’s a venerated badass whose hacking skills put any male geek to shame. At the same time, she is irresistibly feminine.
In real life, Felicia Day is not just another pretty face. The self-proclaimed gamer (cool) launched her own production company (cool) called Geek & Sundry, and she still has plenty of geekiness in her (also cool, to be honest). She's recently voiced a role in the animated series "The Legend of Vox Machina."
Robert Carradine – Revenge of the Nerds
Louis Skolnick is the IT geek prototype. Back in the ‘80s, when a computer whiz was truly nerdy, "Revenge of the Nerds" (1984) totally nailed it. And just look at those glasses!
Louis epitomized someone like Bill Gates. But when Steve Jobs came along with the iPod, the rest of us finally had to admit that possessing digital superiority was a pretty cool asset, after all. Robert Carradine is clearly dashing and a celeb au naturel. The man was born a star. Robert Carradine was literally raised in Hollywood, California, by the prominent Carradine show business family, so yeah, coolness runs through the man's veins.
Josh Saviano – The Wonder Years
In "The Wonder Years," Paul is Kevin’s best bud who is super smart and a total dork. He can barely walk straight. He is debilitated by allergies. He also has a crush on Winnie, but this nerd does not get the girl. And it's not too difficult to understand why.
Granted, Josh Saviano graduated actually from Yale and practices law, but he’s pretty cool anyway. There is even a conspiracy theory that says he is, in fact, Marilyn Manson! When asked about it, he said he is quite happy with people thinking he is a rockstar rather than some dorky kid.
Emma Watson – Harry Potter
Hermione Granger is not just a nerd — she's a magical nerd. "Harry Potter" fans soon realize that her proficiency in spells and concocting magic potions makes her a valuable asset to her classmates.
In real life, Emma Watson has always valued her education. She grew up to be stunning and smart, and she graduated from Brown. Oh, we almost forgot — she also played in her college lacrosse team. So, let's see — looks? Check. Brains? Check. Successful career? Check. Plays sports? Check. Yes, she definitely qualifies for a cool stamp. And she is still killing it in Hollywood!