When: 2005-2010

Larry Clark is most known for his film Kids, but he also tends to creep people out with his sexual portrayals of youth culture, and he didn't disappoint with his Supreme collaboration. He shot an X-rated calendar for Supreme in 2005 and also did a "Teenage Lust" T-shirt for Supreme which featured a naked couple making out. But not everything Clark has done for Supreme has been pornographic—he also shot a 2010 lookbook that's a reminder he's still down with skate culture.