From undocumented workers to an arrest in Florida, the business of busking raises questions about money, immigration and the law.

Times Square is one of the world’s most profitable entertainment districts, but not all its performers work beneath Broadway marquees. Some earn their living on the sidewalks, collecting cash from tourists who stop for a song, a photograph or a moment of amusement. What appears to be 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 result in an arrest elsewhere?

Consider Robert John Burck II, better known as the Naked Cowboy. For nearly three decades, he has entertained Times Square visitors wearing little more than white briefs, cowboy boots, a hat and a guitar. According to a recent Business Insider interview, Burck earns approximately $150,000 annually on average, with his best year reaching $250,000.

His income is not limited to tips. He has developed the Naked Cowboy into a trademarked business, generating revenue from personalized Cameo videos, merchandise-related ventures and other enterprises. In one recent year, he reported approximately $20,000 in street tips and $50,000 from Cameo alone.

Burck is an exceptional example, but his success raises a question that applies to every performer collecting money on the street: How is that income taxed?

The IRS considers money earned through street performance taxable, whether it is received in cash or electronically. Independent performers generally report their business income and eligible expenses on Schedule C, and self-employment taxes may apply. Even without receipts or an employer issuing tax forms, cash earnings must be reported.

The difficulty is accountability. A Broadway theatre has ticket records. A restaurant has sales receipts. A street performer receiving dollar bills from hundreds of tourists may have no independently verifiable record of what was collected. Honest reporting depends heavily on the performer’s bookkeeping.

That does not establish that performers are evading taxes. It does, however, make the question of financial transparency legitimate.

Interestingly, federal tax legislation effective from 2025 through 2028 allows eligible workers, including qualifying street performers, to deduct up to $25,000 in qualifying tips annually from federal taxable income, subject to restrictions. The income must still be reported, and the deduction does not eliminate applicable self-employment taxes.

Then there is the immigration question.

Times Square attracts an international population of performers, including individuals 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 can owe federal income taxes and obtain an Individual Taxpayer Identification Number to file returns. That number does not provide legal immigration status or permission to work.

In other words, someone can be legally obligated to pay taxes on earnings from work they are not legally authorized to perform.

This raises questions about how employment authorization, tax compliance and the city’s regulation of street commerce intersect. Are performers maintaining business records? Are earnings being reported? How does the city enforce its rules consistently among performers operating in the same public spaces? These are questions worth asking without presuming that any particular performer is violating the law.

The Naked Cowboy’s experience outside New York exposes another contradiction.

In March 2021, Burck was arrested while performing at Daytona Beach’s annual Bike Week celebration in Florida. Tourists had been posing for photographs with him and placing money inside his guitar. Police considered the activity a violation of the city’s panhandling ordinance.

The encounter escalated into an arrest for resisting an officer without violence. The panhandling charge was dismissed, while Burck entered a no-contest plea to the resisting charge and received time served, with adjudication withheld.

Burck subsequently sued Daytona Beach and two officers, challenging the ordinance 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 ruled Daytona Beach’s panhandling ordinance unconstitutional.

Here is the irony: a performer can earn substantial taxable income accepting tips in New York, yet face criminal enforcement for similar conduct in another jurisdiction. Tax law recognizes the earnings, but local ordinances determine where and how performers may solicit or accept money.

New York has its own restrictions. In Times Square’s pedestrian plazas, performers requesting or accepting tips must generally remain within designated activity zones. These regulations are intended to prevent congestion, aggressive solicitation and interference with pedestrian traffic.

Such rules serve a purpose. Tourists should not be pressured into paying for unwanted photographs, and sidewalks must remain accessible. Regulation also raises questions about the treatment of independent performers whose livelihoods depend on public space.

There is a difference between an artist entertaining an audience, a costumed character demanding payment and someone simply asking for financial assistance. Yet all three can become entangled in laws governing solicitation, public conduct and freedom of expression.

The larger issue is not whether the Naked Cowboy deserves his reported earnings. He has built a recognizable brand through extraordinary consistency, turning an unconventional performance into a business. Nor is it reasonable to assume that performers who collect cash, speak another language or lack traditional employment arrangements are automatically breaking the law.

The issue is whether the rules governing this highly visible economy are clear, fair and consistently enforced.

Times Square profits from its reputation as a place where anything can happen. Its street performers are part of that attraction, yet the financial and legal structures surrounding their work remain largely invisible to the tourists photographing them.

The Naked Cowboy may own his trademark, but he does not own the sidewalk. The IRS wants its share of the earnings, immigration law determines who is authorized to work, and local government decides where the performance may take place.

For a business that can begin with nothing more than a guitar and a handful of dollar bills, that is a remarkably complicated arrangement.