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(Credit: Far Out / Wikimedia / Picryl)


Exploring Frank Sinatra's favourite drinking spots


As one of the most celebrated actors and singers of his day, it’s no wonder Sinatra liked a drink – he had reason to celebrate, after all. Born in Hoboken in 1915, much of Frank Sinatra’s early life was spent in his parent’s tavern, watching the various characters flow in and out as his mind wandered, imagining himself somewhere far away.

It was also at this time that he began developing an interest in music; a passion that his mother, Dolly, was incredibly encouraging of, perhaps to a fault. While Sinatra would later say that he owed much of his energy and drive to his mother, his fourth wife, Barbara, would later claim that she was responsible for abusing Sinatra as a child.

In 1938, Sinatra got a job as a singing waiter in a restaurant called The Rustic Cabin In New Jersey. That, in turn, landed him a gig on a local radio station and, soon, Sintra was convinced he was destined to be a star, and he wasted no time in letting everybody know.

He wasn’t wrong, either. By May 1941, Sinatra was at the top of the Billboard charts. His charismatic stage persona and big band sound made him intensely popular amongst teenage girls, prompting the rise of ‘Sinatrmania’, which saw the singer access and previously untapped young audience. In the 1950s, Sinatra became an icon of the silver screen as well, appearing in High Society, Guys and Dolls, and countless others.

In his heyday, Sinatra was the toast of all America. He topped every bill, knew every person worth knowing, and appeared at every glamorous party from Chicago to Palm Springs. Here, we take a look at some of his favourite drinking dens.

Frank Sinatra’s favourite drinking spots:

The Palmer House Hotel, Chicago

Address: 17 E Monroe St, Chicago, IL

Website: The Palmer House Hotel

The towering Palmer House Hotel was where Frank Sinatra learned the tricks of the trade. The young Sinatra performed in the hotel’s Empire Room, a dining room famed for its opulence.

With its ornate chandeliers, stunning ceiling fresco and cosy, candle-lit atmosphere, the Empire Room has played host to some of America’s greatest musicians, including Louis Armstrong, Ella Fitzgerald, Judy Garland and Nat King Cole. After his sets, Sinatra would take to one of the neat, circular tables to sip at something strong.

(Credit: The Palmer House Hotel)

The Pump Room, Chicago

Address: 1301 N State Pkwy, Chicago, IL

Website: Sadly, none available.

After checking out of the Palmer House Hilton, Sinatra might stop by for a nightcap at Chicago’s Pump Room. While it was recently forced to close as a result of the Covid-19 pandemic, The Pump Room has been immortalised in the realm of popular culture.

The entrance and lobby, for example, were used for the opening shots of Alfred Hitchcock’s North By Northwest, while Sinatra himself namechecked the drinking establishment in ‘My Kind of Town (Chicago Is)’, singing the line “Chicago is… the jumpin’ Pump Room”.

(Credit: Chicago Eater / Facebook)

Lord Fletcher’s Restaurant, Palm Springs

Address: 70385 CA-111, Rancho Mirage, CA

Website: Lord Fletcher’s Restaurant

A place where it rains but one day a year wouldn’t seem like an obvious setting for a British-themed restaurant, but, nevertheless, Lord Fletcher’s has been a Palm Spring institution since 1966.

Offering sweaty Palm Springians a version of England that exists largely in the imagination, Lord Fletcher’s boasts timber-frame ceiling beams, a roaring fire decorated with pieces of medieval armour, and walls decorated with old London street signs. Sinatra loved the cosy interior so much that he chose Fletcher’s as the venue for his 75th birthday party, introducing both President Ford and Roger Moore to his favourite after-dinner drink, the “royal brandy ice.”

(Credit: Lord Fletcher’s)

Piero’s, Las Vegas

Address: 355 Convention Center Dr, Las Vegas, NV

Website: Piero’s

There are few places that evoke the glamour of Las Vegas in its heyday than Piero’s. Once a favourite haunt of the rich and famous, the drinking den became something of a home-away-from-home for Frank Sinatra, whose protégée Pia Zadora still sings there some weekends.

Offering homely Italian food and all the martinis you can drink, entering this dim-lit dining establishment feels like stepping back in time. With its curving leather booths and mahogany interiors, it’s easy to imagine Sinatra, surrounded by adoring companions, savouring a plate of Pollo Vesuvio with a tumbler filled with a generous measure of Jack Daniels, a drink he liked to savour in the comfort of his private dining room.

(Credit: Piero’s)

La Dolce Vita, Los Angeles

Address: 9785 Santa Monica Boulevard,
Beverly Hills, CA

Website: La Dolce Vita

Whenever Sintra found himself in Beverley Hills, he made a point to stop by La Dolce Vita, a favourite among the ‘Rat Pack’. With the restaurant expertise of Alessandro Uzielli guiding Dolce Vita into a bright new age, it’s a better time than any to experience this unique slice of Hollywood history.

There were places that meant as much to Sinatra as La Dolce Vita – and no wonder. Sinatra was one of the restaurant’s original investors and frequented the establishment regularly. As Uzielli recalls: “Frank would often slide into table number two and hold court over his favourite Veal Milanese, served thin and crispy, and his signature ‘gentleman’s drink’ of Jack Daniel’s. He was always full of energy and profusely kind, from the gift of a gold watch to our dishwasher to offering a Rolls Royce to our maître d—which was politely declined”.

(Credit: La Dolce Vita)