Times Square will always greet you with predictable levels of insanity: fully-grown Elmos pawing at children for pictures, massive billboards flickering for attention, and sidewalks packed with tourists unsure how they’ve ended up in the armpit of the Earth.

It’s also home to some of New York’s most determined entrepreneurs. Walk more than a city block and you will undoubtedly be offered a mixtape from rappers pushing their music from the ground up. “We’re trying to bring it back to those Bad Boy days, back when Puff Daddy was handing out tapes with street promotion teams,” said Sean Hunter, one of the subjects of our Street Dreams documentary.

The rappers operate on donations but the CDs are rarely free. Good luck walking away with a tape without contributing a dollar or two.

Sunny Smack, another Times Square regular, told us that arrests are a daily concern. Charges range from tickets for blocking space to robbery.

But Manhattan doesn’t have a lock on guerrilla marketing—it just happens to be fertile ground for possible clients. Jadon Woodard chooses to take his talents underground, where he freestyles on subway cars with a backpack full of CDs that he trades for any donations. “Most people are scared to promote their stuff on the subways,” Jadon said, “because you have a higher level of rejection than you’ll ever deal with, and you have to perform your work.”

We followed these three artists in their daily routines to get a handle on how and why this underground economy functions. Are they just in it for the money? Is there any real opportunity to be had in petitioning strangers? Does anybody even have a CD player anymore?

Directed by Sean Stout.

Using Format