When: 2008, 2011

It doesn't get bigger in the intersection of art and streetwear than Kaws. His brand, Original Fake, has collaborated with Supreme twice. The first time produced a piece that definitely got people talking. His character wrapped around a bikini-clad Kate Moss, and it drove Supreme's audience nuts. On the second go-around, Kaws re-worked Supreme's logo in graffiti throw-up.