Ed Roth
 

There was a dude in CA by the name of Ed Roth, artist, cartoonist, self promoter, in the late 50s and 60s. He was into the CA youth culture, especially the car culture. He also had a penchant understanding the counterculture attraction to youth.

He capitalized on both by airbrushing t-shirts and sweatshirts with Hot Rod, Surfing, and Hippie/drug images, at car shows. When they became popular he hired a bunch of airbrush artists and sold by mail order, then the most popular designs he had printed by the thousands for sale every place you could think of.

His most famous and best selling character was Rat Fink but he made a fortune selling shirts and decals of the badass counterculture image to suburban kids everywhere.
http://cellar.org/2014/ratfink.jpg

I'm not sure if he was following or leading some of the trends, but he seemed to always tuned in and able to monetize it.
From 1966...
http://cellar.org/2014/roth3.jpg

Heh, "snitch box".

This was my favorite kind of Big Daddy sketch from growing up, seeing them in the car mags. Giant engine, some kind of rat/troll and always, always, the giant gear shifter sticking up out of the vehicle, and the tongue hanging out in the wind.