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.

New York Fashion Week may belong to designers, editors, buyers and the invited few, but on September 8, fashion walked directly into the middle of Times Square and invited everyone to watch.

The Fashion Week Experience’s “Runways on Fire” transformed Father Duffy Square into an outdoor runway, effectively kicking off Fashion Week with a five-hour celebration of emerging designers, international culture, music, entertainment and street-level New York energy. Better yet, it was free. No velvet rope, impossible invitation or carefully guarded front row was required. Tourists, New Yorkers and fashion devotees could simply stop in the middle of Times Square and watch fashion happen around them.

Produced by The Fashion Week Experience in partnership with HealthJox Foundation, Inc., with James Corbett and Dewry DuRoi Bradford behind the production, Runways on Fire was deliberately conceived as something broader than a conventional runway presentation.

The idea was to connect fashion with culture, community and social impact while creating visibility for emerging talent that doesn’t necessarily have access to Fashion Week’s more established rooms.

The HealthJox component gave that mission additional purpose: the New York City nonprofit works with at-risk youth through programs addressing mental health, sports, creativity and career development.

There was something particularly appropriate about doing it in Times Square. Fashion Week can occasionally become so insulated that it forgets clothing ultimately exists outside the fashion industry. Here, the audience wasn’t confined to editors studying a collection from folding chairs. It was New York itself. Models walked against one of the most recognizable urban backdrops in the world as the constantly changing Times Square crowd became part of the show.

The afternoon moved through multiple presentations rather than attempting to impose a single fashion identity. Emerging designers and independent brands were given room alongside entertainment and cultural presentations, creating something closer to a fashion festival than a traditional runway show. The Dan Smith Brand was among those featured, while Trouble to Triumph brought a bold urban-lifestyle sensibility to the runway, styled by @ichepalms_ip. The emphasis was less on retail-ready conformity than personality—giving designers and creatives a chance to show audiences exactly who they were.

Prince Mario-Max

One of the day’s most colorful presentations turned the runway outward, celebrating countries and cultures from around the world. Prince Mario-Max was among those who walked, adding a wonderfully unexpected touch of international pageantry to an event already taking place beneath the sensory overload of Times Square. It worked because Runways on Fire wasn’t pretending to be a hushed Paris salon. It understood its location and embraced it.

That accessibility may have been the event’s greatest strength. There is an enormous amount of conversation within fashion about diversity, inclusion and creating opportunities for new voices, but Runways on Fire made the concept remarkably literal: put the runway in a public square and remove the price of admission. Suddenly the person who never receives a Fashion Week invitation can stand beside the person who attends shows professionally. A young designer can see a possible future. A child walking through Times Square can see models and designers who look like them. Fashion stops being something happening behind a door and becomes something happening in their city.

The partnership with HealthJox Foundation reinforced that idea. Runways on Fire was designed not simply to promote clothing but to use fashion and entertainment as vehicles for youth empowerment, mental-health awareness, community engagement and opportunity. HealthJox describes its larger mission as helping young people develop practical skills and pathways toward sustainable careers, making fashion one part of a considerably larger conversation about possibility.

Prince Mario-Max and one of the founders and coordinators

There would be plenty of polished rooms, celebrity arrivals, champagne, impossible shoes and carefully curated guest lists in the days that followed. That is Fashion Week, too, and frankly, some of us rather enjoy it. There was something refreshing about beginning this one outside.

Suzanna Bowling and Prince Mario-Max

Before New York Fashion Week disappeared behind its doors, Runways on Fire put fashion in the middle of Times Square and let the city have the first look.

Times Square smelled considerably better than usual Wednesday afternoon as Taste of Times Square returned September 9, turning Broadway and Restaurant Row into one enormous outdoor dining room. More than 30 neighborhood restaurants participated in the annual Times Square Alliance food and music festival, which stretched along 46th Street from Seventh to Ninth Avenues and across the Broadway plazas between 45th and 47th Streets.

For four hours, the neighborhood became a tasting menu of itself. Italian, Mexican, Caribbean, Cuban, Indian and classic American dishes appeared within steps of one another, with longtime Theatre District institutions joining newer arrivals and giving New Yorkers and visitors the chance to graze their way through the neighborhood without committing to a full dinner. Most tastes were priced at $5, with several larger offerings at $10.

Among the participating favorites were Bond 45 NY, Brooklyn Chop House, Ellen’s Stardust Diner, Hard Rock Cafe, Carmine’s, Becco, Havana Central, Le Rivage, Junior’s, Serendipity 3, Toloache, Tony’s Di Napoli and Virgil’s Real Barbecue. It was a rather wonderful reminder of something those of us who actually live and work here already know: Times Square may be famous for its lights and Broadway theatres, but there is an extraordinary amount of food tucked into these blocks.

Toffee Sticky Pudding from The Long Room

We started with dessert—or at least made very certain we didn’t miss it. The Toffee Sticky Pudding from The Long Room proved one of our happiest discoveries of the day. Sweets were surprisingly scarce, particularly compared with the number of savory offerings, making that pudding even more welcome. Between it, Serendipity 3’s Frozen Hot Chocolate and Junior’s cheesecake, the neighborhood’s sweet tooth was represented, but only just.

Toloache’s pork taco

Then came Toloache. Their pork taco was delicious enough to accomplish exactly what an event like Taste of Times Square is supposed to accomplish: it made us want to go back and review the restaurant properly. A few bites can be a far more persuasive advertisement than any press release.

Palermo Argentinian Bistro Steak and cheese bread

We already knew what Palermo Argentinian Bistro could do, having previously reviewed and loved the restaurant, but its steak and cheese bread provided a useful reminder. The steak was quite simply melt-in-your-mouth tender. There is also another Mexican restaurant, Rosa Mexican, preparing to enter the neighborhood, and we are more than ready to see what it brings to the increasingly interesting Theatre District dining scene.

Food, however, was only half the atmosphere. Music spilled through the plazas, including TSQ LIVE + MTA Music performer Bella Breen at Broadway and 47th Street, while the Broadway Dreams Foundation and Ellen’s Stardust Diner’s Stardusters were among the scheduled performers farther downtown. Street musicians filled in the spaces between, and at one point models were being filmed in the middle of it all. It was Times Square doing what Times Square does best: food, theatre, fashion, music and complete visual chaos somehow occupying the same few blocks without asking one another’s permission.

Catherine Russell

One of our favorite encounters was with Catherine Russell, who has spent nearly four decades playing Margaret Thorne Brent in the Off-Broadway thriller Perfect Crime. Russell isn’t simply part of Theatre District history; she is one of those people who actually makes the neighborhood feel like a neighborhood. She owns The Theater Center and Patzeria Perfect Pizza, and there she was Wednesday, not posing beside the booth but serving pasta to the people who stopped by.

That accessibility is part of what made Taste of Times Square work. For one afternoon, the barrier between restaurant and customer, performer and audience, Broadway and sidewalk largely disappeared. Restaurant owners and workers served food in the street while musicians performed a few feet away and thousands of people wandered from table to table deciding what smelled too good to pass up.

New York has an unnerving ability to place celebration and violence almost side by side.

Just a block from Restaurant Row, two people were stabbed Wednesday afternoon inside a West 47th Street building. Early reports differed on the precise address, ages and conditions of the victims, but police confirmed that a man and woman suffered stab wounds in the incident at approximately 2:45 p.m. Later reporting said both victims had been taken to Mount Sinai West and were in stable condition, while police were searching for a suspect. Contrary to some initial information circulating Wednesday, the latest reporting I found does not confirm that the male victim died or that a person of interest was in custody.

The contrast was impossible to ignore. A block away, people were eating tacos, listening to music and celebrating the restaurants that make Hell’s Kitchen and Times Square feel like home. Nearby, police were investigating a bloody act of violence.

That, too, is New York: glorious and maddening, communal and frightening, sometimes within a single city block.

For most of Wednesday, though, Taste of Times Square offered the version of the neighborhood worth fighting to preserve. Restaurants opened themselves to strangers, performers turned sidewalks into stages, Catherine Russell handed out pizza, and thousands of people ate their way through a community that is far richer and more local than the flashing billboards sometimes allow the rest of the world to see.

Somewhere in all of that, we discovered a sticky toffee pudding worth going back for.

Broadway will go dark for a moment on Tuesday, September 8 at 6:45 p.m., when the marquees of all 41 Broadway theatres dim simultaneously in memory of 13 artists and industry figures whose work helped shape the theatre—and, in several cases, American culture far beyond it.

The September Broadway in Memoriam tribute will honor Tim Curry, Clive Davis, Gina Ferrall, Josh Grisetti, Jeff Hamlin, Glen Hansard, Louise Lasser, Anna Louizos, Seth Marquette, Dolly Parton, Anne Russell, James Walsh and Harold Wheeler.

There is something particularly moving about the Broadway tradition of dimming the lights. Theatre is built on illumination—the marquee, the footlights, the spotlight—and so Broadway marks loss by taking that light away. For a few moments, Times Square becomes noticeably darker, acknowledging that someone who contributed to its brilliance is no longer here.

This September’s list crosses nearly every corner of the industry. Tim Curry, forever associated with his indelible Dr. Frank-N-Furter in The Rocky Horror Show, was also a three-time Tony Award nominee whose Broadway career included Amadeus, My Favorite Year and Spamalot. Dolly Parton, whose songs, personality and unmistakable generosity made her one of America’s most beloved entertainers, also left her mark on Broadway through 9 to 5: The Musical and the theatrical projects that followed.

Clive Davis, Nancy Pelosi

Clive Davis, one of the towering figures of the recording industry, spent decades influencing the music that ultimately found its way onto stages as well as records. Glen Hansard, whose music helped give Once its singular heartbeat, became part of Broadway history when the intimate musical defied conventional Broadway expectations and captured the 2012 Tony Award for Best Musical.

Broadway will also remember the extraordinary orchestrator, composer, conductor and musical director Harold Wheeler, whose career stretched across decades and included work on The Wiz, Dreamgirls, The Full Monty, Hairspray and countless other productions. Wheeler’s contribution was often the kind audiences feel without necessarily knowing whose hand created it—the musical architecture beneath some of Broadway’s most memorable nights.

Anna Louizos and Ken Billington in The Producers Exhibit Photo credit Rebecca J Michelson

Theatre designer Anna Louizos gave physical form to stories through a career that included scenic and costume work and multiple Tony nominations.

Louise Lasser Photo Magda Katz

Louise Lasser, best known to much of America through television and film, also had roots on the New York stage. Gina Ferrall, Jeff Hamlin, Seth Marquette, Anne Russell and James Walsh will likewise be remembered for lives and careers connected to the Broadway community.

Josh Grisetti

For T2C, the inclusion of Josh Grisetti carries particular weight. Grisetti, who died at only 44, possessed the kind of talent that made an audience look twice: an actor with comic precision, musical intelligence and an individuality that could not be manufactured. His work ranged from the stage to television and film, but those who saw him in the theatre understood exactly what Broadway has lost.

The September ceremony is part of the relatively new Broadway in Memoriam initiative, established last year to create a more consistent and inclusive way of honoring members of the theatrical community. Rather than allowing recognition to depend upon sporadic individual marquee dimmings, the quarterly tradition gathers multiple members of the Broadway family into a shared remembrance.

The ceremony now takes place four times annually, on the second Tuesday of September, December, March and June, with all 41 Broadway theatres participating simultaneously. The committee can also designate a separate dimming for an individual whose contribution to Broadway is considered profoundly significant.

Members of the Broadway community may submit creative professionals who have worked on Broadway, as well as career professionals who devoted their lives to the industry, for future consideration. The next submission deadline is November 17, for the December 8, 2026 dimming. Information and submissions are available through Broadway in Memoriam.

Broadway is an unusual place. Shows disappear. Sets are struck. Costumes are packed away. Dressing rooms are emptied and another name eventually goes above the theatre door. An industry devoted to creating moments that vanish every night has always had a complicated relationship with permanence.

That is why September 8 matters.

At 6:45 p.m., Broadway will briefly extinguish the lights that ordinarily announce who is playing, what is opening and what audiences should see next.

For that moment, the darkness will say something else entirely:

We remember who was here.