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Frank Sinatra spent the nights after his New York performances posted up at a handful of his favorite bars and restaurants, drinking with celebrity friends until just before the sun rose. He valued this time with his friends, so much so that he didn’t ever want it interrupted. One of his confidants shared the words that the singer never wanted to hear while he was out. 

A black and white photo of Frank Sinatra standing in front of a microphone at a New York concert hall.
Frank Sinatra | William Gottlieb/Redferns

Frank Sinatra used to host dinner parties at several select New York restaurants

Those close to Sinatra knew that he never went to dinner alone. He had a selection of New York restaurants he frequented, and he always invited guests to join him.

“He grew up as an only child, and he vowed that, as an adult, he would always have people around him,” Mark Simone, a frequent dinner guest of Sinatra’s, told the New York Post.

Hardly anyone would turn down an invitation from Sinatra, but Simone said that guests didn’t expect to actually speak to him during the meal.

“If he invited you to dinner, you’d be honored,” he explained. “But dinner was 27 people. You’d be lucky if you were 14 seats away from him.” 

At one meal, comedian Jerry Lewis, seated at the other end of the table from Sinatra, left for a moment. Soon, a waiter gave Sinatra a telegram that read, “Frank — pass the salt. Jerry.”

His friend shared the phrases the singer never wanted to hear while out

Sinatra’s level of fame meant that restaurants catered to him at hours they would not otherwise take customers. One Thanksgiving, when Sinatra’s marriage to Ava Gardner was ending, he had nowhere to go, so he booked a table at a New York restaurant. Though it was closed, the owner instructed his staff and their families to come dine so that the restaurant would be full when Sinatra arrived.

When Sinatra finished a performance, he always wanted to go out for a drink afterward. Often, this meant arriving at bars and restaurants into the early morning hours. 

If he was in New York and couldn’t find anything open, Sinatra and his friends would go back to the Waldorf Astoria, where he stayed while in the city. Here, the staff had orders to open up the bar and ballroom for Sinatra and his friends, no matter the hour. The singer never wanted to hear that a place was closed or was planning on closing for the night. 

“The only words he never wanted to hear,” said TV producer George Schlatter, “were ‘take two’ and ‘last call.'”

“Take two” meant more work on set for Sinatra and “last call” meant the night was over. Sinatra did not ever want to hear either.

Frank Sinatra reportedly used to tip very well

Even though Sinatra’s demands on restaurant staff bordered on the outrageous, they knew that they would end the night with a significant tip in their pockets. Per the Desert Sun, Sinatra used to carry a gold clip with only $100 bills. Because of this, every time he tipped, he handed out at least $100.

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On one occasion, Sinatra handed a young shoeshiner $100 and asked if that was the biggest tip he’d ever received. When the boy said no, Sinatra gave him another $100 bill to make it the biggest tip he’d ever received.