DOTD For Friday, December 12, 2025

A Gentleman's Drink, For The Chairman Of The Board

Today’s DOTD - Drink Of The Day - is a “Frank’s Way” Cocktail, inspired by the birth date one of the all-time greatest musicians - and drinkers - Francis Albert Sinatra. Frank was born on this date, December 12, 1915 in Hoboken, New Jersey, to Italian immigrants Anthony Martin “Marty” Sinatra, a Sicilian immigrant who worked as a boxer, firefighter, and bar owner, and Natalina “Dolly” Garaventa, an Italian immigrant who was a strong neighborhood figure, politician, and midwife.

Ol’ Blue Eyes himself, one of the best-selling music artists of all time, sold more than 150 million records worldwide during his lifetime, and even more since his death. That’s pretty good for a guy who never learned to read music, had an ear drum permanently perforated at birth, and who started by belting out songs for spare change while sitting atop the player piano in his parents’ tavern in Hoboken.

Frank Sinatra could very definitely sing - and act a little too - & he grew up to know more than a little bit about living life well. That included visits to bars around the world, drinking, hanging out with the Rat Pack, and holding court for whomever was at the bar. He was such a beloved regular at some watering holes, he had his own chair or barstool.

Frank Sinatra’s mug shot for seduction of a married woman on November 27, 1938

Much like the nuggets of wisdom Shawn & Jody drop here at The Politics Bar, Sinatra was known for dispensing nuggets of wisdom too. For example, “You only go around once, but if you play your cards right, once is enough.” There’s also Frank’s ode to drinking, “I feel sorry for people that don’t drink because when they wake up in the morning, that’s the best they’re going to feel all day.”

He was cocky, sure, but he could back it up with talent & charisma. So it’s no wonder Frank Sinatra was considered ‘Chairman of the Board’, the nominal leader of the Rat Pack, after the death of the group’s founding leader, Humphrey Bogart. The Rat Pack was a legendary group of entertainers, known for their charismatic performances, camaraderie, and lavish lifestyle in 1960s Las Vegas. They included Dean Martin, Sammy Davis, Jr., Peter Lawford, and Joey Bishop, among others.

Even before the Rat Pack existed, Frank got a tip in 1947 from the comedian Jackie Gleason, about what the best drink in the world was. That tip was simple: Jack Daniel’s, on the rocks. For Sinatra, that tip became love at first sip, and Jack Daniels soon became Sinatra’s favorite spirit. He was even buried with a bottle of Jack Daniel’s Black Label.

Frank’s connection with the Jack Daniel’s brand was more than just preference though. As the legend goes, at a performance in 1955, Sinatra carried a rocks glass with ice & Jack onstage, and announced to the crowd, “Ladies and gentlemen, this is Jack Daniel’s and it’s the nectar of the gods.” The next year, Jack Daniel’s annual distribution doubled from 150,000 cases to 300,000.

Indeed, Frank Sinatra ended up being Jack Daniel’s first real brand ambassador even though such a term was unknown at the time. He’d take shots like this one, on the roof of the iconic Capitol Records building in Hollywood, Jack Daniels in hand, that the distiller would then use in all kinds of advertising.

It’s not as though Frank couldn’t afford all the sauce he wanted. After WWII, Sinatra was pulling in up to $93,000 a week just for a busy radio appearance schedule. But Jack Daniel’s knew a good thing when they saw it, making sure Sinatra’s glass was never empty, & there was always a case in his dressing room wherever he went. In return, he’d allow them to use phrases he’d toss out about Jack Daniels like, “This is a gentleman’s drink.”

Sinatra was a simple man in some ways, with a wry sense of humor, that came across both in his drinking and in other ways. In 1967 actress Dinah Shore put together a celebrity cookbook titled Cooking With The Stars. Dean Martin and Frank Sinatra both submitted recipes, and both are classics, but Frank’s is generally regarded as better - and a perfect example of his humor.

Martin Burgers:

1 lb. ground beef
2 oz. bourbon – chilled

Preheat a heavy frying pan and sprinkle bottom lightly with table salt. Mix meat, handling lightly, just enough to form into four patties. Grill over medium-high heat about 4 minutes on each side.

Pour chilled bourbon in chilled shot glass and serve meat and bourbon on a TV tray.

Sinatra Burgers:

1. Call Deano.

2. Tell him to make you a f****n’ burger.

3. Drink his bourbon.

With Sinatra’s simple recipe in mind, today’s Drink Of The Day is a Frank’s Way cocktail, Jack Daniels, the way Frank Sinatra liked it, or what’s sometimes known as a 3:2:1. Jack.

Ingredients

Here’s what you’re going to need for this drink: