Go inside the family-owned business where big shots like Frank Sinatra and Rudy Giuliani have gotten their cigars for decades

In the midst of Midtown Manhattan’s modern hubbub, you can stumble upon a place that’s a step back to an entirely different time. . 

Celebrating 85 years in operation this year, the family-owned-and-operated Nat Sherman brand has weathered the trends to remain the preeminent American brand of cigars. The townhouse itself has been a favorite hangout of everyone from Frank Sinatra to former mayor Rudy Giuliani.

Inside the smoke-filled parlor, you’ll find an eclectic mix of patrons, antiques, and distinctive tobacco products. Take a tour back in time with us, below.

The anachronistic storefront on busy 42nd Street, dwarfed by the neighboring modern high-rises, is an indicator of the throwback world you’ll find within.

Step inside and into a narrow, high-ceilinged shop decked out in dark wood, old-school store counters and a lingering haze of tobacco smoke. Nat Sherman started his namesake shop during the Prohibition era in the Garment District before the company moved to Fifth Avenue and then opened up in its current location in a full townhouse.

This is a family business, helmed by the three grandchildren of Nat Sherman. Larry Sherman, pictured, knows the name of everyone in the store and strikes up regular conversations with customers.

The Sherman siblings — from left, Bill, Michele, and Larry — have worked together as the third generation in their family business for 25 years. With backgrounds in sales, business, and fashion, they each bring their own twist to the endeavor.

In the mid-1900s, cigars were a mark of status. “You could tell a man’s worth by the shoes he wore and the cigar he smoked,” Michele Sherman told us. Today, with indoor smoking limitations, the Shermans see cigars as a kind of luxury product.

Visitors are brought to the back to find the perfect cigar for their tastes. The room, like a wine cellar for cigars, is kept at 70 degrees and 70 percent humidity for optimal cigar storage conditions.

Inside, you can find nearly a thousand different facings of cigars from around the world, all stored on the organized shelves. They can range from about $5 to as much as $50 a piece.

One shop assistant seeks out a specific cigar for a customer. Nat Sherman prizes their ability to offer a personalized experience: they encourage each customer to speak to an employee to make the perfect choice.

Cliff Gold, lead sales associate, is one of the experts who guides visitors and matches their tastes to the right product. Each associate is a certified tobacconist — and looks the part. “We dress to our best-dressed customers,” Michael Herklots, the company’s vice president, told us. “It’s a mark of pride.”

Their best-selling cigar is the Nat Sherman Host Hobart, which goes for $5.75 each, or $157.50 for a box of 25. Since cigars are about the price of a fancy cup of coffee, it’s what the Shermans call an “affordable luxury”, and a habit that appeals to “all walks of life.”

To mark the 85th anniversary of the brand, they’ve released a Limited Edition 85th Anniversary cigar made of Nicaraguan and Dominican components. It’s $217.50 for a box of 10, and was designed with input from tobacconists from across the country.

Nat Sherman also produces 23 varieties of cigarettes, which are sold in tobacco stores and convenience shops across the US. Back in the heyday of cigarettes, Nat Sherman would produce customized versions for special events or high-profile clients; Frank Sinatra was apparently partial to an orange paper, which matched the interior of his airplane.

In the corner of the shop, a light-up section shows off the high-end Dupont brand lighters and smoking accessories. These lighters can cost upwards of $200 each.

Here’s one of those fancy lighters in action.

Pipes, once popular, decorate this wall as emblems of an era gone by.

These funky animal figurines are actually beer steins. Periodically, they’ll host events at the clubhouse where the steins come in handy.

The player piano on the upstairs mezzanine has been used by the likes of Harry Connick, Jr., who played it at the former location of the townhouse on Fifth Avenue.

For those who don’t have an entire room to dedicate to cigar storage, a humidor is the usual approach. This antique lacquered humidor is decorated like a European-style house. Most are made of Spanish cedar.

The Shermans think of the townhouse as a democratic space where everyone is welcome and people of all walks of life can feel at home. “There is not a person who can’t afford to come in and enjoy a Nat Sherman cigar, no matter who they are or what they do,” Herklots said.

But downstairs, you’ll find the clubhouse. This space is reserved for members, who pay a $3,000 annual fee that also functions as store credit. It’s a dimly-lit, smoky haven of relaxed chat, and members sprawl comfortably on the worn furniture.

Club members are given personalized lockers to store their cigar stashes. There are currently a few hundred members, and many others are on a waiting list.

Here’s the locker belonging to former New York City Mayor Rudy Giuliani. The Shermans recall a time when Giuliani, prepping for a keynote address at his nearby office, badly wanted to smoke — so he popped into the townhouse to finish practicing.

Despite the long-standing history, the Shermans see their company as an innovator in the space, constantly putting out new products while maintaining their focus on quality. “That’s one of the things that as a family we’re most proud of — we can afford to not compromise,” Bill Sherman, pictured, said.

“Cigars bring people together. That has not changed,” Larry Sherman said.