Coolness was founded on the TV show Parker Lewis Can't Lose. This show was originally based on the teenage cult classic Ferris Buelers Day Off, however the writers stepped up and earned their paychecks and made something special. Like many FOX comedies that suffer without a real audience (Family Guy, Arrested Development), PLCL died in obscurity. Coolness itself doesn’t denote supreme awesomeness. Instead it connotates a very chill relaxed attitude.
"That girl keeps walking by and checking you out..."
"Coolness, give it a while, let her sweat it out"