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.”
Patrick Dempsey – Can’t Buy Me Love
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.
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.
Tobey Maguire – Spider-Man
Director Sam Raimi’s Peter Parker, brought to us by actor Tobey Maguire, goes out of his way to make Spider-Man’s alter-ego as dorky as humanly possible. The Marvel comic book character finds his roots as a high school orphan from the Queens borough, and so does this Peter Parker. This could make him the most authentic Spidey.
Spider-Man was a $100 million success story at the box office and the most successful comic hero movie ever. You can say that makes actor Tobey Maguire pretty darn cool. And the fact that he reprised the role for "Spider-Man: No Way Home" makes him even cooler in our books.
Jaleel White – Family Matters
Steve Urkel is a classic nerd. In fact, we would go as far as to say that when you think of TV nerds, it's impossible not to think of Urkel. With a nasally high-pitched voice, super high-waisted pants, and coke-bottle glasses, he is a grotesque caricature.
He shows his cool side in "Family Matters" when he transforms into Stefan Urquelle by drinking a magic potion. Interestingly, Stefan's character is the actor’s normal self. Just think of all the coolness he had to reign in to become Urkel! But Jaleel White is a real handsome, cool dude in real life, as you can see in this picture alone.