14 Foods And Drinks Frank Sinatra Absolutely Loved

During his illustrious six-decade career, Frank Sinatra amassed an impressive collection of accolades, including 10 personal Grammys, three Oscars, two Golden Globes, an Emmy, and a Peabody. In his personal life, he was often seen mingling with icons like Dean Martin, Sammy Davis Junior, and Tony Bennett, while also enjoying romantic involvements with starlets such as Ava Gardner and Marilyn Monroe. Yet, beyond the glitz and glamour, Sinatra's approach to food was surprisingly simple. His favorite foods and drinks told a story, a blend of his Sicilian heritage, boozy escapades, and a genuine sweet tooth.

In our exploration of Frank Sinatra's culinary world, we delve into the dishes that defined the Chairman of the Board's palate, unveiling the tales behind the flavors that brought him comfort and added richness to his extraordinary life. Beyond discovering his favorite foods and drinks, we'll step into the New York restaurant frequented by Sinatra, where his close relationship with the chef meant his dishes always came tailor-made. We'll also share which whiskey brand he helped popularize and unveil which dessert he ordered every week without fail.

With a bit of a bad boy reputation, it might be difficult to picture someone like Frank Sinatra indulging in wholesome pleasures like grabbing a treat from his local pastry shop. However, Sinatra was a man filled with surprises, and this extended to his culinary preferences. One of his preferred spots for satisfying his sweet tooth was Veniero's, a family-owned Italian bakery located on East 11th Street in Manhattan.

Sinatra's chosen pastry at Veniero's was the Biscotti Regina — a crunchy, nutty, lemony cookie adorned with sesame seeds. Although its name translates to "the queen's cookie," these delectable treats also go by more comical names such as strunzi di sciocca (translated as chicken's droppings) and strunzi d'ancilu (aka angel's droppings). Originating from Sicily, the same region as Sinatra's family, these bite-sized delights are crafted from a shortcrust dough made with flour, sugar, butter, and egg and infused with lemon or orange zest. Typically enjoyed with coffee, tea, or sweet wine, these treats likely connected Sinatra to his Sicilian heritage.

While it's important to acknowledge their impressive achievements and charisma, some celebrity habits are undeniably bizarre. Take, for instance, Mariah Carey, who insists on having 20 humidifiers in her bedroom for a good night's sleep. Interestingly, these eccentric behaviors seem to persist even after death, with many famous individuals expressing unique burial requests.

Frank Sinatra is a prime example. When the Sultan of Swoon passed away in 1998, his casket contained a flask of Jack Daniel's whiskey. Sinatra's affinity for the Tennessee bourbon began in 1947 when his friend Jackie Gleason introduced him to it during a night out. Sinatra not only fell in love with the drink on the spot but also went on to declare it the finest liquor in the world, often sipping it on stage in between songs. His preferred way to enjoy Jack Daniel's, now known as the 3-2-1, involves three rocks, two fingers of whiskey, and a splash of water.

When you glance at Sinatra's favorite foods — sweets, alcohol, and loads of pasta — it might seem like his diet wasn't exactly aligned with the Food Guide Pyramid. However, Ol' Blue Eyes made sure to include some veggies in his diet. More specifically, he was a fan of the arugula salad from Patsy's restaurant in Manhattan.

In Sinatra's time, Patsy's prepared the salad with zero frills. It was just arugula leaves dressed with olive oil, red wine vinegar, and some shredded fresh basil. Eating a salad composed entirely out of these peppery, slightly bitter greens might not sound appealing to a lot of Americans (it only became popular in the United States in the 1990s after all), but these greens have long been a favorite in Sinatra's ancestral Italy. Perhaps it's this connection that drew Sinatra to the simple salad. Or maybe it was the fact that it's often served alongside veal Milanese, one of Sinatra's other favorite dishes.

If you're not familiar with the concept of a rider, let us break it down for you. Before singers, bands, or performers go on tour, they send a list of requirements to the venues where they'll be performing. Some of these details are technical, like stage size and lighting, while others get a bit more personal. Think of specific flowers, candles, and personal care products. Food and drink preferences are another aspect where the star's unique tastes come to the forefront.

Sinatra was no exception when it came to having particular food and drink requests for his riders. In a 1991 rider from Sinatra, there were requests for a fruit bowl, brie and crackers, sandwiches, chips, and pretzels. But the real surprise? Mini Tootsie Rolls. It turns out the legendary singer had a soft spot for these tiny chocolate candies. He reportedly liked them so much that some accompanied him to his final resting place, adding a sweet touch to the Jack Daniel's and Camel cigarettes he was also buried with.

Like many Italian Americans, Frank Sinatra had a soft spot for pasta, and he definitely had his favorites. Among the top contenders was fusilli with garlic and anchovies from the iconic Patsy's Restaurant in Manhattan. Being a bit particular, Sinatra asked for a lighter touch of garlic, as he wasn't a big fan of the allium.

To cater to Sinatra's taste, Chef Patsy Scognamillo would sauté six cloves of garlic in olive oil for just two minutes. After golden and fragrant, he would remove the cloves with a slotted spoon. This technique ensured that the dish retained the essence of garlic without dominating the overall flavor. Following this, a combination of onions, anchovies, and herbs such as basil and parsley were introduced to the flavorful oil. The resulting sauce was generously spooned over al dente fusilli pasta and finished with a touch of toasted breadcrumbs. Buon appetito, indeed.

Named after Posillipo, a picturesque residential area along the Bay of Naples known for its stunning views and exceptional seafood eateries, this dish ranked high among Sinatra's favorites at Patsy's. Although it's also known as zuppa di vongole (clam soup), it's important to clarify that it's not your typical American-style soup. Instead, it boasts a thin marinara sauce that generously coats the delectable clams.

The dish starts by boiling top neck or littleneck clams. After cooking, a portion of the cooking liquid is set aside until it's time to make the sauce. Moving on, garlic cloves are sautéed in olive oil until just fragrant. Given Sinatra's aversion to overpowering garlic, Chef Patsy made sure to remove the cloves as soon as possible when preparing the dish for the famous crooner. The clams then join the fragrant oil, mingling with crushed whole tomatoes and the reserved cooking liquid. Seasoned with salt, pepper, and a medley of fresh herbs like basil and parsley, the ingredients meld together in a brief simmer before being generously spooned over the clams. This versatile dish can be savored on its own as an appetizer or served over pasta for a satisfying main course.

It's no secret that Frank Sinatra was quite the aficionado when it came to his adult beverages. Unsurprisingly, he had a list of go-to drinks that he ordered on repeat.

Along with his 3-2-1 Jack Daniel's (three ice cubes, two fingers of Jack, and a splash of water) and the many Rusty Nails he shared with his Rat Pack pals, Sinatra was often spotted enjoying martinis. His gin of choice for this classic cocktail was Beefeater's, complemented by just a splash of vermouth. Although it's unclear whether he preferred them shaken or stirred, one thing was certain — Frank liked his martinis ice-cold and dry. For that reason, he always ordered them on the rocks with a generous twist of lemon. So if you want to try a simple drink the singer savored, this is an easy one to try for yourself.

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