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.

The cult-favorite bagel sensation is bringing its Grip, Rip and Dip philosophy to the Crossroads of the World, complete with exclusive flavors and a Broadway-worthy opening celebration.

New Yorkers have very strong opinions about their bagels. We debate the crust, the chew, the schmear, and whether a proper bagel should ever be toasted. We have elevated the humble combination of flour, water and yeast into something approaching a civic religion. So when a company comes along and suggests that perhaps we’ve been eating our bagels all wrong, it had better have something extraordinary to offer.

Enter PopUp Bagels, the cult-favorite brand that made a name for itself by stripping the traditional New York bagel experience down to its most delicious essentials. Following its successful Greenwich Village debut, the company is bringing its unconventional approach to Times Square, with a grand opening scheduled for Friday, October 16, at 7 a.m.

Forget the towering breakfast sandwiches, elaborate toppings and architectural feats of balancing smoked salmon, tomatoes and onions between two halves of bread. PopUp Bagels has a different philosophy: serve the bagels hot, sell them whole and let the customer do the rest.

Its trademarked Grip, Rip and Dip® approach is as uncomplicated as it sounds. Take a freshly baked bagel, tear off a piece and plunge it into a generously flavored schmear. There are no knives required, no carefully constructed sandwiches and certainly no need to pretend that eating a bagel should be an exercise in restraint.

It’s a clever reinvention of a New York ritual, turning something traditionally eaten on the run into an experience that’s meant to be shared, sampled and savored. The emphasis is on the bagel itself, with its crisp exterior and warm, chewy interior, rather than the mountain of ingredients that so often threatens to overwhelm it.

Naturally, the Times Square location isn’t arriving quietly. PopUp is marking its Broadway-area debut with a pair of flavors that could hardly be more New York if they arrived in a yellow taxi.

First comes the New York Cheesecake Strawberry Schmear, a playful tribute to one of the city’s most enduring desserts. The combination brings the richness of cheesecake and the sweetness of strawberries into PopUp’s signature dipping experience. It’s breakfast flirting rather shamelessly with dessert, and frankly, we see no reason to object.

Then there’s a collaboration that should get the attention of even the most opinionated deli traditionalists. PopUp has joined forces with the legendary Katz’s Delicatessen to introduce Everything but the Pastrami Butter, a distinctly New York creation that brings together two institutions with very different approaches to the city’s culinary traditions.

Katz’s, of course, is practically synonymous with the oversized pastrami sandwich, a Lower East Side institution whose reputation has endured for generations. PopUp, meanwhile, has built its following by rejecting the sandwich altogether. Bringing the two together is a delicious bit of culinary irony, and one that feels particularly appropriate for a city where tradition and reinvention are constantly competing for the last word.

For purists, the regular menu remains reassuringly familiar. Plain, Everything, Poppy, Salt and Sesame bagels provide the foundation, while the schmear selection includes Plain and Scallion Cream Cheese, Salted Butter and Brown Sugar Cinnamon Butter. The choices may sound straightforward, but simplicity is the entire point. When the bagel is good enough, it doesn’t need a supporting cast of fifteen ingredients.

Because this is Times Square, where even breakfast occasionally deserves its own opening-night celebration, PopUp is planning something considerably more festive than simply unlocking the doors.

The October 16 grand opening will feature a live DJ, exclusive New York City merchandise for the first customers in line and complimentary beverages courtesy of Saint James, La Colombe and Natalie’s. Early arrivals will have the advantage, although given the brand’s enthusiastic following, a line seems almost inevitable.

The new shop will also offer something particularly welcome in a neighborhood whose schedule rarely resembles the traditional nine-to-five workday. Open daily from 7 a.m. until 9 p.m., the Times Square location will have the latest closing time of any PopUp Bagels shop in New York City.

That makes it an appealing prospect not only for commuters and breakfast enthusiasts, but also for the theatre crowd. A warm bagel and an inventive schmear before an evening performance, or a quick bite after a matinee, may prove an attractive alternative to the neighborhood’s more predictable dining options.

There is something wonderfully New York about the whole enterprise. PopUp Bagels isn’t trying to replace the city’s beloved bagel institutions. It’s challenging the assumption that there is only one correct way to enjoy a food that New Yorkers have spent generations perfecting.

And while the company may have eliminated the traditional sandwich, it certainly hasn’t eliminated personality. Between its Katz’s collaboration, cheesecake-inspired schmear and celebratory opening, PopUp seems to understand that in Times Square, a little showmanship is practically mandatory.

The real test, naturally, will be in the bagel itself. New Yorkers will forgive a great deal of theatricality, but never a mediocre bagel.

PopUp Bagels opens its Times Square location on Friday, October 16, at 7 a.m., with daily hours from 7 a.m. to 9 p.m. For additional information, visit popupbagels.com.

Most people hire the first firm that answers the phone. That is understandable after a serious injury, and it is also how good claims end up undervalued. Consultations in San Diego are free and firms expect to be interviewed, so treat the meeting as one. These nine questions separate a firm that genuinely handles pedestrian claims from one that treats yours like a rear-end collision with a bigger hospital bill.

Question 1: How many pedestrian cases have you handled, specifically?

Car crash volume does not translate. Pedestrian claims turn on sight lines, lighting, crossing behavior, and vehicle speed rather than skid marks and property damage. Listen for: real examples and named corridors. Firms with a dedicated pedestrian accident attorney in San Diego practice, such as HHJ Trial Attorneys, cite specific county data, including the eight corridors where roughly 30 percent of these crashes happen. Long-established firms such as CaseyGerry can point to decades of similar files.

Question 2: Will you retain a reconstruction expert, and when?

Vehicle damage is repaired, video is overwritten, and signal timing records get purged. Listen for: a firm that talks about preservation letters and scene inspection in the first weeks, not after the demand is rejected.

Question 3: Who will actually work on my file?

You may meet a partner and never speak to one again. Listen for: a named attorney and a named case manager, plus a straight answer on response times.

Question 4: How will you handle the claim that I crossed outside a crosswalk?

Since the Freedom to Walk Act took effect in 2023, crossing outside a crosswalk is no longer routinely ticketed in California, but insurers still raise it to argue comparative fault and cut the payout. Listen for: a concrete plan, usually driver speed analysis, visibility distance, and whether the driver was distracted.

Question 5: Could a government entity share responsibility?

Faded markings, a burned-out streetlight, an obstructed sign, or a badly timed signal can put the city or county in the case. Listen for: awareness that claims against public entities generally require a government claim within six months, not the usual two years.

Question 6: Have you looked at my own auto policy?

Many pedestrians never think of this. In California, uninsured and underinsured motorist coverage on your own auto policy applies when you are struck as a pedestrian, and it often covers household family members too. Listen for: a firm that asks for your declarations page at the first meeting.

Question 7: What exactly are your fees and costs?

Under Business and Professions Code 6147, a contingency agreement must be in writing, must state the rate, must explain how costs affect your net recovery, and must state that the fee is not set by law and is negotiable. An agreement missing those elements is voidable by the client. Listen for: a clear percentage, whether it rises if suit is filed, and who advances expert costs.

Question 8: How do my medical bills get handled meanwhile?

Unpaid bills going to collections while a case is pending is one of the most common complaints injured people have. Listen for: a firm that coordinates health insurance, hospital liens, and treatment on a lien basis where needed, and that explains how those liens get negotiated down before you see your share.

Before you sign anything

Take the fee agreement home and read it. Ask for the answers to questions 5, 6, and 7 in writing. Interview two firms rather than one, since the difference in approach usually becomes obvious side by side.

Pedestrian injuries are among the most severe on San Diego roads, and the first offer rarely reflects future surgeries, lost earning capacity, or long-term care. HHJ Trial Attorneys and the other established firms in the county all offer free consultations, so asking these nine questions costs you nothing but an hour. Ask them before the insurer’s deadline pressure starts, not after.

Only in New York would it make perfect sense to take Monet, Klimt, Redon and Cross out of the museum and put them in your makeup bag.

Two decidedly New York institutions have come together for the limited-edition Bobbi Brown x The Met Collection, pairing the beauty brand born in New York City with The Metropolitan Museum of Art and transforming details from some of its celebrated works into objects considerably more portable than a masterpiece. The result is part makeup collection, part miniature art exhibition—and considerably easier to take home from The Met.

The collaboration draws upon works by Henri-Edmond Cross, Gustav Klimt, Odilon Redon and Claude Monet, translating their colors and imagery into packaging that makes opening an eyeshadow palette feel just a little more decadent. It is an inspired pairing because cosmetics and painting have always shared a language: color, shadow, light, texture and the occasional illusion.

At the center of the collection is an eight-well eye shadow palette filled with golds, bronzes and browns in matte and shimmering finishes—the sort of shades that can move easily from an understated New York afternoon to an evening when understated has left the building. A three-in-one Brightening Blush offers that elusive lit-from-within flush, while the Luxe Eye Shadow provides multidimensional shimmer for anyone who believes eyelids deserve their own little work of art.

The lips haven’t been neglected. Bobbi Brown’s Luxe Lipstick gets the museum treatment with skincare-infused color and a pressed, canvas-inspired bullet, while the Extra Lip Tinted Balm delivers a sheer, pH-reactive wash of color with plumping hydration. In other words, one can now contemplate great art while simultaneously wondering whether one needs another lipstick. We know how that usually ends.

The cleverness of the collaboration lies in the packaging. Rather than simply stamping The Met’s name onto a cosmetics case and calling it culture, the collection brings actual works from the museum’s holdings onto the pieces themselves. The compacts become tiny canvases, turning something normally destined for the bathroom counter into something you may be reluctant to throw away once you’ve hit pan.

There is also something wonderfully New York about the entire enterprise. The Met has spent more than 150 years collecting objects of beauty from across civilizations. Bobbi Brown built its reputation on a distinctly modern idea of beauty. One hangs masterpieces on Fifth Avenue; the other gives us the tools to create our own faces before heading out the door.

High art and highlighter were probably destined to meet eventually. The limited-edition Bobbi Brown x The Met Collection is available now through Bobbi Brown Cosmetics.

You may not be able to hang a Monet in your apartment, but apparently you can now keep a little piece of The Met on your vanity.

During Climate Week NYC, New York is awash in conversations about saving the planet. There are panels and pledges, statistics and speeches, dire predictions and ambitious promises. But at the heart of The Footprint of Life Gala, held September 24 at CORE Club, was a considerably more personal question: What are you going to leave behind?

Hosted by Green Vision Foundation co-founders Amy Green and Gary Green, the annual black-tie evening brought together environmentalists, philanthropists, athletes, scientists, business leaders, artists and advocates around the idea that influence carries responsibility. We all leave a footprint. The question is whether that footprint simply records where we have been or actually improves what remains after us.

That distinction gave the evening its purpose. The Footprint of Life was created to harness the collective power of its guests to protect the planet, transform lives and create a lasting legacy for generations to come. This year, its focus expanded the conversation by bringing together sport, philanthropy and global leadership—not as separate worlds, but as forces capable of moving people in ways institutions alone often cannot.

Amy Green

Adam Mett, Amy Green

The evening honored Adam Met, founder and executive director of Planet Reimagined, whose rather unusual résumé makes perfect sense in this context. Musician, educator and climate advocate, Met has taken the reach afforded him by one world and applied it to another. Through Planet Reimagined, he has brought researchers, advocates, policymakers and partners together with the goal of moving climate ideas beyond conversation and into scalable, actionable solutions.

The second honoree came from an entirely different arena. Legendary big-wave surfer Garrett McNamara was recognized for using sport as a force for change, accepting the honor on behalf of Laureus Sport for Good. As a Laureus Ambassador, McNamara represents an organization built around the premise that sport can be far more consequential than competition. Laureus works with children and young people around the world, using sport to help overcome violence, discrimination and disadvantage.

That partnership also made an intriguing point about environmentalism. We tend to separate issues into convenient categories—climate over here, poverty over there, education somewhere else, human rights in another room entirely. Real life isn’t nearly so tidy. Environmental degradation affects communities. Poverty affects opportunity. The health of oceans affects livelihoods. The future of children cannot really be separated from the future of the world they will inherit. The Footprint of Life placed those connections at the center of the evening rather than treating conservation as an isolated cause.

“The Footprint of Life is about recognizing that every one of us leaves an impact—and deciding together what we want that impact to be,” Amy Green told guests. “By bringing extraordinary people into one room, we had an opportunity to turn conversation into collaboration and individual influence into collective action. This evening was ultimately about the world we leave behind and the lives we have the power to change now.”

And it was quite a room.

Among those gathering for the black-tie dinner was legendary oceanographer and Mission Blue founder Dr. Sylvia Earle, whose presence alone provided a living connection to decades of ocean conservation. She was joined by philanthropist and Giving Back Foundation founder Meera Gandhi, television personality Melissa Gorga, former New York City Mayor Eric Adams, Lava for Good founder and CEO Jason Flom, Bank of America Executive Vice Chair Julian Mylchreest, MLB All-Star Joey Votto, former NBA player and coach M.L. Carr, and human-rights advocate Ilwad Elman.

my Green

Amy Green

Fashion and design were represented by Alejandra Alonso Rojas, Andrew Kwon and Nicole Fuller, while actor and filmmaker Randall Batinkoff, environmental justice advocate Saad Amer, We The Planet founder Kunal Sood, real estate developer and entrepreneur Tony Cho, and Laureus U.S. Ambassador Kely Nascimento were among the evening’s other guests.

It made for the kind of eclectic guest list that could only really happen in New York: oceanographers beside athletes, fashion designers beside human-rights activists, financiers beside environmentalists. Yet that was precisely the point. Solving enormous problems requires people who don’t normally inhabit the same rooms to begin talking to one another.

There is always a danger with galas devoted to serious causes that the glamour overwhelms the reason everyone has gathered. Champagne is considerably easier than climate change. A beautiful dinner is easier than conservation. A photograph beside a step-and-repeat is certainly easier than changing the way we live.

But glamour and purpose don’t have to be enemies. A room filled with people who possess money, visibility, expertise, access or influence is also a room filled with resources. The real measure comes afterward: what happens when everyone goes home?

The Footprint of Life is built around that question. Not whether we leave a footprint—we have no choice about that—but what kind of footprint it will be.

Because legacy isn’t ultimately what we say we cared about.

It is what is different because we were here.

The Footprint of Life was presented in partnership with Laureus Sport for Good and supported by Cerity Partners, The Twenty Five, Privé and Worth Magazine.