I Sipped It My Way: How to Drink in the Spirit of Sinatra

Frankie’s greatest hits are paired with classic cocktails by Ol’ Blue Eyes fan/Jones bartender Eric Tecosky

Today is Frank Sinatra’s birthday, which really should be a holiday. After all, the man was bigger than life. He counted the mob and JFK as pals, and bombshell Ava Gardner was his wife. He won an Academy Award and has three stars on the Hollywood Walk of Fame. Even 16 years after his death, people still try to emulate him, his style, his charisma, his way of life.

“I feel sorry for people that don’t drink, because when they wake up in the morning, that is the best they are going to feel all day.” ― Frank Sinatra

As much as we’d like to imagine Sinatra sipping on elegant Martinis and Manhattans, he only stuck with Jack Daniel’s. It was always served thusly: two fingers of “Daniel’s,” as he called it, poured in a tumbler filled with three ice cubes and a splash of water. You never really saw him without it in his hand — he drank it every day well into his 80s, and was even buried with a bottle of JD. Hey, the man knew what he liked.

But to celebrate Sinatra’s birthday today, I say play his greatest hits while sipping on your own favorite cocktail. In honor of the occasion, I asked longtime Sinatra fan and Jones bartender Eric “ET” Tecosky to pair a few of the Chairman’s greatest hits (linked below to Spotify) with classic cocktails.

Tecosky, who was first introduced to Sinatra by his father, loved his music and movies even at an early age and grew to appreciate his real guy-ness. “I can’t remember if it was Sinatra or Jimmy Page that ‘inspired’ me to drink Jack Daniel’s, but the more I can add to the ‘things in common with Frank Sinatra’ category in life, the better. If only I could sing,” Tecosky laments.

“Strangers in the Night” with the Vieux Carré: “There’s something sexy and mysterious about going out and not knowing where the night may take you … and there’s not a better town for this to happen in than New Orleans.”

“Summer Wind” with the Negroni: “The summer is easy, it’s light, it’s smooth. Day blends into night with a cool breeze, like a Negroni.”

“That’s Life” with the Martini: “No one promised you easy. And if it’s gonna be tough, we should take a moment to simplify and un-complicate things once in awhile. A classic martini is just what the doctor ordered in these situations.”

“One For My Baby (And One More For The Road)” with the Old Fashioned: “It’s late, you should be home, but you’re all in tonight … so if you’re gonna do it, then do it. Whiskey all the way. A little bitter, a little sweet, just like the life decision you are currently making.”

The Lady Is a Tramp” with the Manhattan: “A woman who knows what she wants. She doesn’t play games and does not have time to get caught up in nonsense. The female Frank Sinatra! Straightforward, simple, yet refreshingly, the perfect blend. Like this cocktail.”

If you’re looking for a party today, however, The Room Hollywood is throwing a 24th anniversary Sinatra Party where formal attire is required, “no excuses.” The Nice Guy in West Hollywood will be playing Sinatra tunes all night while running a Gentleman Jack special.

For those staying in, Saucey, the liquor delivery app, is running a promo with Jack Daniel’s where anyone who orders from them (4 to 7 p.m.) and uses the code “Sinatra” will possibly win a visit from ol’ Blue Eyes himself. Well, an impersonator, but the guy will be taking requests and might even make you a drink!