From undocumented workers to an arrest in Florida, street trading raises questions about money, immigration and the law.
Times Square is one of the most profitable entertainment districts in the world, but not all of its artists work under Broadway marquees. Some earn their living on the sidewalks, collecting money from tourists who stop for a song, a photo or a moment of entertainment. What seems like spontaneous entertainment is actually an economy worth examining. Who keeps track of the money? Who pays taxes? Why is the same activity permitted in New York and subject to arrest elsewhere?
Consider Robert John Burck II, better known as the Naked Cowboy. For nearly three decades, he entertained visitors to Times Square wearing little more than white briefs, cowboy boots, a hat and a guitar. According to a recent Business Insider As of the interview, Burck earns about $150,000 per year on average, with his best year reaching $250,000.
His income is not limited to tips. He grew Naked Cowboy into a trademarked business, generating revenue from custom Cameo videos, merchandise-related businesses, and other businesses. In one recent year, he reported about $20,000 in tips and $50,000 from Cameo alone.
Burck is an exceptional example, but his success raises a question that applies to any artist raising money on the streets: How is this income taxed?
The IRS considers money earned from busking to be taxable, whether received in cash or electronically. Self-employed artists generally report their business income and qualified expenses on Schedule C, and self-employment taxes may apply. Even without receipts or an employer issuing tax forms, cash income must be reported.
The difficulty is responsibility. A Broadway theater has ticket registers. A restaurant has sales receipts. A street performer who receives tickets from hundreds of tourists may not have an independently verifiable record of what was collected. The honesty of the reports depends heavily on the accounting of the performer.
This does not mean that performing artists escape taxation. However, this legitimizes the question of financial transparency.
Interestingly, federal tax law effective from 2025 to 2028 allows eligible workers, including eligible street performers, to deduct up to $25,000 of qualified tips per year from federal taxable income, subject to restrictions. The income must still be reported and the deduction does not eliminate taxes applicable to self-employment.
Then there remains the question of immigration.
Times Square attracts an international population of artists, including people who speak limited English. Their immigration status cannot be determined from their language or appearance, and there is no reliable public evidence establishing how many street performers are undocumented.
Nevertheless, the legal distinction is significant. An undocumented immigrant may have to pay federal income taxes and obtain an individual taxpayer identification number to file returns. This number does not provide legal immigration status or authorization to work.
In other words, a person may be legally required to pay taxes on income from work that they are not legally authorized to perform.
This raises questions about how work authorization, tax compliance and the city’s regulation of street trading intersect. Do artists keep professional records? Are income declared? How does the city enforce its rules consistently between artists performing in the same public spaces? These are questions worth asking without presuming that any particular artist is breaking the law.
The Naked Cowboy’s experience outside of New York reveals another contradiction.
In March 2021, Burck was arrested while performing at the annual Daytona Beach Bike Week celebration in Florida. Tourists posed for photos with him and put money into his guitar. Police considered the activity a violation of the city’s panhandling ordinance.
The encounter degenerated into an arrest for resisting a police officer without violence. The panhandling charge was dismissed, while Burck pleaded no contest to the resisting charge and was sentenced to prison, with sentencing denied.
Burck then sued Daytona Beach and two officers, challenging the order and alleging violations of his constitutional rights. In 2022, the city agreed to a $90,000 settlement without admitting wrongdoing. Two years later, in a separate case, a federal judge declared Daytona Beach’s panhandling ordinance unconstitutional.
Here’s the irony: An artist can earn substantial taxable income from accepting tips in New York, while still facing criminal prosecution for similar behavior in another jurisdiction. Tax law recognizes earnings, but local ordinances determine where and how artists can solicit or accept money.
New York has its own restrictions. In Times Square pedestrian plazas, performers asking for or accepting tips are generally required to stay within designated activity areas. These regulations are intended to prevent congestion, aggressive solicitations and interference with pedestrian traffic.
Such rules serve a purpose. Tourists should not be forced to pay for unwanted photos, and sidewalks should remain accessible. The regulations also raise questions about the treatment of independent artists whose livelihoods depend on public space.
There is a difference between a performer entertaining an audience, a costumed character demanding payment, and someone simply asking for financial assistance. However, these three elements can be mixed up in laws governing solicitation, public conduct and freedom of expression.
The biggest issue isn’t whether the Naked Cowboy deserves his reported winnings. He built a recognizable brand through extraordinary consistency, turning an unconventional performance into a business. It is also not reasonable to assume that artists who collect money, speak another language, or lack traditional terms of employment are automatically breaking the law.
The question is whether the rules that govern this highly visible economy are clear, fair and consistently applied.
Times Square benefits from its reputation as a place where anything can happen. Its street artists are part of this attraction, but the financial and legal structures surrounding their work remain largely invisible to the tourists who photograph them.
The Naked Cowboy may own his brand, but he doesn’t own the sidewalk. The IRS wants its share of the income, immigration law determines who is allowed to work, and local government decides where representation can take place.
For a business that can start with nothing more than a guitar and a handful of dollar bills, it’s a remarkably complicated arrangement.
Gn bussni
