7. Jay Kay
The Jamiroquai singer was never seen with a bare head when his British band shot to fame in the nineties, but even as his band sunk back to anonymity, his head gear continued to have notoriety. There is even a Facebook page honoring his hats. Many of the hats were designed by his mother including the one on his head in the silhouette that serves as the band's logo making him look like a dead ringer for Bullwinkle the Moose.
The Motörhead and Hawkwind bassist's hat of choice is a mish-mash of two of the most manly professions a little boy could dream of. It is the shape and size of a cowboy's hat and it's black and it has the skull of a pirate on it.
5. Lady Gaga
Hers is more of a lifetime tribute award to her eclectic collection than for any specific brand of headwear. From a turtle to a telephone, anything inspires hats for this pop star.
4. Pharrell Williams
Williams might be the most successful recording artist of the century having produced everyone from Britney Spears to Jay Z to Snoop Dogg's "Drop It Like It's Hot," appearing on Daft Punk's "Get Lucky" and Robin Thicke's "Blurred Lines." But it wasn't until he appeared on the Grammys with that puffy brown concoction taken from an Arby's sign on his head to perform "Happy" that your Grandmother knew who he was.