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Turner G. Cowles/Money Magazine

In 1998, Robert John Burck flew to California to do a photo shoot with Playgirl magazine. He went on the beach in jeans and a flannel shirt. The photographer suggested he go out in just his underwear. "I did it, went out in my underwear and made over $100," he says.

"I've been doing it ever since."

Burck says he was performing in Times Square for three years before he took any money for his performances. But soon after he started accepting tips, being the Naked Cowboy became a very big business; he's even a spokes-cowboy for an oyster company. The Naked Cowboy spent some time with Money explaining all the financial angles of being the Naked Cowboy. Here's what he has to say.