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.

Rusty Nail

The name doesn't sound all that appealing, but Frank Sinatra and the rest of the Rat Pack were able to look past the questionable moniker and enjoy the drink underneath. Called a Rusty Nail, this two-ingredient cocktail is a 1-to-1 or 2-to-1 blend of Scotch and Drambuie, a golden-colored liqueur made out of Scotch whisky, heather honey, herbs, and spices. Most often, it's served on the rocks with a twist of lemon.

A common after-dinner drink, the history of the Rusty Nail is murky. Many believe it was invented for the 1937 British Industries Fair. Others point to 1960s bartenders at the 21 Club in Manhattan as the inventors of the drink. Either way, it gained lots of popularity in the fashionable clubs of New York City and New Orleans in the 1960s and '70s. While the drink certainly had legs of its own, Sinatra's fondness for the libation is often cited as one of the main reasons for the drink's fame. In fact, the "My Way" singer was often spotted ordering Rusty Nails at P.J. Clarke's, a trendy saloon in Manhattan.

Biscotti Regina

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.

Lemon ricotta torte

Owned by the Scognamillo family since 1944, Patsy's is a traditional Italian restaurant in Midtown Manhattan that evokes a bygone era. In addition to its authentic look and feel, the establishment boasts an impressive client list that includes celebrities like Michael Bublé, Al Pacino, and Liza Minnelli. However, it was Sinatra's frequent visits in the 1950s that put Patsy's on the map.

While the renowned singer had a penchant for main dishes like veal Milanese, stuffed artichokes, and fusilli with garlic and anchovies (more details on those later), he always saved room for dessert. One of his favorites was the lemon ricotta torte — a simple yet decadent creation resembling a cheesecake. Patsy's crafts this delightful treat using an impressive three pounds of whole-milk ricotta cheese, combined with familiar ingredients like sugar, eggs, butter, and flour. The distinctive touch comes from the addition of lemon juice and zest. All of the ingredients are mixed and then baked for 55 minutes on the bottom rack of the oven. After a few hours in the fridge, the tantalizing torte is ready to be savored.

Jack Daniel's whiskey

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.

Veal Milanese

Also known as Cotoletta alla Milanese, veal Milanese is a celebrated dish hailing from the Northern Italian city of Milan. The dish starts with veal cutlets, tenderized and coated in flour and egg wash. After dredging and dipping, the meat is covered with a flavorful blend of breadcrumbs, parmesan cheese, oregano, and parsley. From there, the breaded cutlets are pan-fried in vegetable oil, resulting in a golden and crispy exterior. Once cooked, the meat is typically served with a lemon wedge and a choice of either an arugula salad or french fries.

Frank Sinatra was a fan of this comfort food dish and frequently ordered it at Patsy's, a Manhattan eatery he frequented during his visits to the Big Apple. Thanks to Sinatra's regular visits, chef Pasquale "Patsy" Scognamillo mastered the art of preparing the dish to Sinatra's exact liking — paper-thin cutlets fried to extra crispy perfection. Unfortunately, it seems that Patsy's no longer serves this iconic dish. Nevertheless, you can bring the taste home by following this veal Milanese recipe directly from Patsy's cookbook.

Arugula salad

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.

Entenmann's crumb coffee cake

Frank Sinatra's culinary preferences often reflected his deep connection to his Italian heritage, with dishes like Biscotti Regina, linguine di pomodoro, and veal Milanese gracing his list of favorites. Being a New Jerseyite added another layer to his palate, with local treats quickly becoming one of his preferred options. Among these, Entenmann's, a Bayshore, Long Island bakery located not far from his Hoboken hometown, held a special place in Sinatra's heart.

But not just any Entenmann's treat would do. Sinatra only had eyes for the coffee crumb cake. Sinatra's love for this treat was so profound that he established a weekly standing order for it in the 1950s. This delectable creation boasts a moist yellow cake adorned with cinnamon-infused crumbles and a dusting of powdered sugar. Ideal for pairing with a hot beverage or enjoying as an afternoon pick-me-up, it's easy to understand Sinatra's affection for this sweet sensation. Fortunately, the legacy lives on. Entenmann's has expanded over the years, making Sinatra's cherished coffee crumb cake readily available in supermarkets across the country.

Tootsie Rolls

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.

Stuffed artichokes

If it wasn't clear before, Frank Sinatra spent a lot of time at Patsy's Restaurant in Midtown Manhattan. According to Patsy's proprietors, the Scognamillo family, The Voice had a dedicated table tucked away in the back of the restaurant. In a show of their unwavering loyalty, the family even went so far as to open the restaurant exclusively for him on Thanksgiving Day when he was down on his luck in the early 1950s. Another testament to their allegiance to Sinatra is found in the famous stuffed artichoke dish.

Sinatra loved pretty much everything about this particular dish, however, he did have one hang-up — the garlic content. Chef Patsy, eager to satisfy Sinatra's preferences, reduced the amount of garlic to suit the singer's aversion to the pungent bulb. Beyond the garlic adjustment, the Scognamillo recipe involves filling hollowed-out artichokes with a mixture of breadcrumbs, black olives, Parmesan, capers, herbs, and olive oil. Following a covered bake for 75 minutes, the artichokes spend a few minutes browning under the broiler for an additional layer of flavor.

Fusilli with garlic and anchovies

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.

Linguine di pomodoro

Don't be misled by the sophisticated Italian name: Linguine di Pomodoro is essentially pasta with tomato sauce. While there isn't a specific tale about Sinatra's fondness for this dish, it's not hard to understand why he cherished it. Picture it: quality pasta bathed in flavorful tomato sauce and topped with freshly grated Parmesan cheese — a quintessentially Italian delight.

Although Sinatra was known for his love of dining out, he was also quite the cook, and it's easy to picture him preparing this uncomplicated dish at his Twin Palms mansion in Palm Springs. Sinatra's preferred recipe kicks off with sautéed onions, followed by the addition of canned Italian plum tomatoes and basil. The concoction simmers for about 30 minutes. Prosciutto and butter are then introduced to the mix, simmering for an additional 15 minutes. Meanwhile, linguine is cooked until al dente and is then graced with a generous spoonful of tantalizing sauce and a hearty sprinkling of Parmesan cheese.

Clams Posillipo

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.

Sunday sauce

Many countries have a special recipe reserved for Sunday family meals. In Britain, there's Sunday roast, Spaniards, especially those from Valencia, favor paella, and the French often opt for roasted potatoes and baked chicken. Never one to sleep on an opportunity for a big family meal, Italian Americans also have a cherished weekend tradition — Sunday sauce. Also known as Sunday gravy or sugo, it's a meaty tomato sauce that simmers on the stove all afternoon, destined to be generously spooned over spaghetti come dinnertime.

The beauty of Sunday sauce lies in its diversity. Every family has a unique recipe. Some incorporate pork shoulder and Italian sausage, while others prefer the richness of short ribs. Ultimately, the specific ingredients matter less than the tradition and the precious time spent with family. While we may not have precise details on how Sinatra put his spin on this quintessential meal, we do know it held a special place among his favorite dishes.

Gin martini

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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