Frank Sinatra's 13 Favorite Dishes And Drinks

It's no exaggeration to say that Frank Sinatra was — and is — an icon. One of the biggest stars of the 20th century, Sinatra was many things to many people: A singer, a movie star, a film producer, and a symbol of America. However, who was the man behind the myth? Well, you can tell a lot about a person from the kind of food that they ate, and Sinatra's eating habits are pretty well-documented.

As a cultural titan that was simultaneously glamorous and relatable, it probably comes as no surprise that Sinatra liked the finer things in life, but that those things were embedded in fairly standard tastes that didn't differ too much from everyone else's. Many of Sinatra's favorite dishes spoke to his Italian heritage, with meals like veal Milanese, fusili with filetto di pomodoro, and classic tomato sauce on heavy rotation. Elsewhere, he displayed a pretty strong sweet tooth, as evidenced by his love of lemon ricotta torte and crumb cake. As for what he liked to drink, Ol' Blue Eyes liked his cocktails simple but punchy, composed of a few good ingredients (and sometimes just the one). If you've ever wanted to dine like the King of the Crooners, you've come to the right place.

Frank Sinatra was born to Natalina Della Garaventa and Saverio Antonino Martino Sinatra, two Italian immigrants who moved to New Jersey before giving birth to their son. Sinatra's love of food, and his tastes, would be significantly shaped by his cultural lineage. So it's little surprise that dishes like veal Milanese were a regular staple in his diet. Sinatra would frequently order this dish at Patsy's Italian Restaurant, an eatery in New York that he helped make famous through his patronage. Patsy's became a go-to spot not just for Sinatra but also his family, and for a host of celebrities with Italian heritage. Sinatra even had his own table at the restaurant, and if you head there today, it's hard to escape his legacy.

Although neither of Frank Sinatra's parents were from Milan, that didn't stop him from enjoying the veal Milanese at Patsy's. To make it, chefs would first make the breadcrumbs from scratch, before coating veal cutlets and frying them in hot oil until crispy and golden. Interestingly, if you were to dine at Patsy's today, you may not be able to order the veal Milanese straight off the menu – it's no longer on there, and you'll have to settle for a couple other veal dishes instead. However, if you eat there on a day associated with Sinatra, don't be surprised if it's offered as a special.

We love a cocktail that can be made with barely any hassle, and it turns out that Frank Sinatra did too. Sinatra's favorite cocktail, the Rusty Nail, requires just two ingredients and hits the spot every time. The world's most famous crooner was largely responsible for making this cocktail a hit in the 1950s (even though it had been invented a couple of decades before this), when his love of the Rusty Nail became well-known. He particularly enjoyed ordering it when he drank at P.J. Clarke's Restaurant & Bar in New York City, where he'd park up at Table 20, but he was also known to rustle Rusty Nails up for friends in his trailer.

As for how the Rusty Nail comes together, it really is as simple as mixing Drambuie and Scotch. You generally need double the amount of Scotch to Drambuie, with the latter liqueur amping up the drink's sweetness and giving it a peppery edge. Needless to say that this makes the drink pretty punchy — and with a name like the Rusty Nail, it's hardly a subtle experience. However, neither was Sinatra himself, and so the man and the drink go rather well together.

You may associate Sinatra's dining habits with intensely savory dishes, heaping steaks, and strong cocktails, but the singer had a consistent sweet tooth. Plus, he didn't always want to partake in these sweet treats in a restaurant, but rather in the comfort of his own home. Sinatra developed a particular affection for Entenmann's crumb cake, a delicacy that you can still buy to this day. The crooner was such a fan that he would have the cakes specifically sent to his 4,500 square foot home in Palm Springs, and did so for a number of years.

The creator of Entenmann's crumb cake, Martha Entenmann, had a story that somewhat mirrored Sinatra's himself. Like the singer, Martha Entenmann started with nothing but grit and determination. While Sinatra would ignite his passion for performing through singing at local nightclubs, eventually building his way up to the big leagues, Entenmann began her career as a bakery salesgirl, later building her brand to mammoth proportions. It's unclear whether Sinatra felt any affinity with Entenmann for these reasons — it's more likely that he just really liked the cake.

Although a lot of Frank's favorite dishes were meaty and fairly heavy, he knew how to keep it light every now and again. When he was dining at Patsy's in New York, he did this with an arugula salad. This dish acted as a counterpoint to the other meals he would order at the famous restaurant, and gave Sinatra his daily greens while he dined on his mains of clams, pasta, or fried veal.

The arugula salad that he liked the most was a simple affair. Instead of being drowned in heavy dressings, it was served lightly coated in olive oil and red wine vinegar. A few small slivers of basil would give the salad a fruitiness and a heady fragrance, and tied into the pepperiness of the arugula leaves and the olive oil well. Chefs would steer clear of putting raw garlic in the salad, due to Sinatra's preference to keep flavors on the gentler side. Although he preferred the arugula salad, we wouldn't be surprised if he'd also tried Patsy's famous chopped iceberg lettuce salad, which has been on the menu for generations.

Is there any cocktail that's classier than a dry martini with a twist? Probably not — and as the embodiment of class itself, it's only natural that Frank Sinatra was a fan of this drink. Although the singer generally leant towards whiskey-based cocktails, he had a particular soft spot for a gin martini. He'd often order the drink when he was in London, where he'd drink at The American Bar while staying at The Savoy. True to the country that he was in, Sinatra would order his martini made with Beefeater gin, with a dash of vermouth and a lemon twist to give it a citrusy edge.

One thing that he was very specific about when it came to this drink was its temperature. Sinatra's martini was all about the ice: The glass had to be filled to the brim with it, and if the drink wasn't super cold, it wasn't right. This, of course, goes against the standard image of a martini, which tends to be served in a glass on its own to avoid it getting watered down. For Sinatra, though, the temperature was more important than the intensity.

If you look at Frank Sinatra's food tastes, a few things stand out — namely that he liked things to be sweet, and also enjoyed a pop of citrus in his dishes. These two things married in his love of lemon ricotta torte. Like many of his other favorite meals, he'd order this torte when he dined at Patsy's, his favored New York haunt and preferred location for a quality Italian meal. The ricotta in the torte itself spoke to Sinatra's own Italian roots, but we're willing to bet that he was largely ordering it because it was delicious.

If you look at the recipe for the lemon ricotta torte at Patsy's, you can see why. For every three eggs, the restaurant used (and uses) a three pound container of ricotta cheese, with several cups of sugar to sweeten things up. Needless to say that this isn't a light treat, but Sinatra definitely worked up an appetite with all of that singing — so can you blame him?

Although Sinatra's love of meat and pasta is no secret, he was also no stranger to vegetables. When he ate them, though, he clearly liked them to be flavorful. If you need any proof of this, check out one of Sinatra's favorite appetizers, stuffed artichokes. These 'chokes were on regular rotation for him when he ate at Patsy's. Although the restaurant would traditionally make its stuffed artichokes with a hefty hit of garlic, for the crooner they toned things down a little bit, as Sinatra was famously not a massive fan of the allium.

You can see why Sinatra was such a big fan of these stuffed artichokes. Each vegetable was generously crammed with breadcrumbs, herbs, anchovies, cheese, and olives, and capers, with a hit of pepper to add some spice. The moisture was then supplied in abundance with olive oil, and once they were loaded up and good to go, they were then placed in a water bath, covered, and cooked in the oven. They emerged soft, juicy, and bursting with complex flavor.

Few love affairs between man and drink are as well-documented as Frank Sinatra's kinship with Jack Daniel's whiskey. For Sinatra, there simply was no alternative to Jack Daniel's, a liquor that he largely helped put on the map. Back when Sinatra was in his prime, Jack Daniel's was a relatively small brand: Although it had a long, storied history, it wasn't exactly the behemoth that we know it to be today, and was still pretty regional. However, a famous endorsement from Sinatra changed everything. In 1955, the singer walked out on stage with a glass of Jack Daniel's, and declared it to be the nectar of the gods. Pretty soon, everybody wanted to try Frank Sinatra's favorite whiskey, and in just a couple of years it had doubled its output.

As for how Sinatra liked to drink his Jack Daniel's, it was pretty simple. He preferred to enjoy it with three rocks of ice and a small splash of water, to help unlock its flavors. Sinatra would pour two fingers at a time — enough to feel the effect, but not enough to overwhelm the palette. As a consequence of Frank Sinatra's devotion to the brand, salesman Danny Campo was tasked with ensuring that he had a constant supply of it on tap. That's a pretty nice pay-off, huh?

Sinatra was a fairly big fan of seafood, and it showed up in a fair few dishes that he enjoyed, like stuffed artichokes — but it wasn't always the main event. That wasn't the case when he ate at Patsy's, though. In the fabled Italian restaurant, Sinatra liked to eat its clams Posillipo, a traditional Neapolitan dish with a briny, winey flavor. Clams Posillipo, which is named after the residential area in Naples, consists of littleneck clams simmered in a combination of white wine, clam stock, and marinara sauce. This sauce is infused with the intense flavors of anchovies and nduja, a fiery Calabrian pork sausage which provides punchy spice to the automatic dish.

With clams Posillipo, though, it's all about the finishing touch. The clams and the accompanying stock are ladled over toasted pieces of bread, daubed with olive oil and rubbed with garlic (although given Sinatra's well-known preference for milder garlic flavors, maybe Patsy's took it easy here). Covering the bread with the clams and liquid allows their juices to soak right through, and the bread makes the dish way more substantial and filling.

Frank Sinatra's name is practically synonymous with Las Vegas: He was virtually the voice of the city, performing in it countless times and imbuing it with a sense of glamor and glass. It's little surprise, therefore, that he had to find meals that he enjoyed eating while he was there — and he landed on a favorite whose name feels like the city itself. Clams casino was a dish that Sinatra regularly ordered at Golden Steer Steakhouse, an eatery that he'd regularly dined at when he was in town. Before he ordered the strip steak, Sinatra would start his meal with this appetizer, paired with a glass of Jack Daniel's.

Unlike his other favorite clam dish, clams Posillipo, clams casino was a fairly complicated and extravagant affair. The dish consisted of steamed half-shell clams topped with a heady mix of pancetta, peppers, onions, and garlic. Imbued through the whole thing was the flavor of gin, which gave the clams a peppery, herbal flavor and an intensity from the alcohol in the dish. Oh, and the clams were steamed not in regular water, but in gin and tonic. We told you it was fancy.

As a world-famous celebrity, Frank Sinatra was likely used to being waited on hand and foot. Sometimes, though, he liked nothing else than to get into the kitchen and roll his sleeves up. One of his staples was a fresh tomato sauce, which he demonstrated how to make live in a 1974 episode of "Dinah's Place," broadcast on NBC. This was a speedy dish: Sinatra could rustle it up in about 15 minutes, and it was delicious every time.

Sinatra's recipe for tomato sauce was simple, but effective: He sautéed pieces of garlic and onion in a pan with plenty of olive oil, before adding freshly blended tomatoes. As the sauce was cooking, Sinatra would boil his pasta of choice — and once the two things were done, he'd just combine the two together, presumably taking the chunks of garlic out before doing so. As Sinatra wasn't a massive fan of garlic, avoiding chopping the cloves down too much would help keep the flavor light, and not distract from the flavor of the tomatoes themselves.

When Sinatra was in his prime, so was steak. Steakhouses were everywhere, especially in Las Vegas, where the crooner was frequently found performing. Well, after a successful concert on the Strip, what better than a Strip steak to get his energy back? That's what Sinatra frequently found himself eating at Golden Steer Steakhouse, his restaurant of choice in the City of Sin.

What's interesting about Sinatra's choice of New York Strip was that unlike a lot of other folks, he didn't go for heavy steak sauce. Instead, he preferred a pizzaiola sauce. This light topping is a combination of tomatoes, garlic, oregano, parsley, white wine, and a little roux to bring everything together and prevent it from being too runny. This sauce is practically bursting with freshness, and when placed on a New York Strip, it prevents the meat from feeling too dense or intense. Oh, and in case you were wondering: He liked his New York Strip cooked medium rare.

Everyone likes pasta, and Frank Sinatra was no exception. The famous singer was known to be a fan of the pasta at Patsy's, and when there he would often order fusilli with filetto di pomodoro. This appeared to be a fairly easygoing dish of fusilli shapes combined with chopped tomatoes, which were presumably cooked until rich-tasting and utterly delicious. As Sinatra would frequently pair this with dishes like clams Posillipo and veal Milanese, we'd imagine that he didn't want to weigh it down too much with additional ingredients. Sometimes, the simple things really are the best.

This wasn't the only pasta dish that Sinatra liked, either. He was also known to enjoy fusilli with garlic and anchovies, again at Patsy's, which would be topped with gently browned breadcrumbs. With basil and parsley in the dish, as well as the punchy main ingredients, this was a pasta that sang with flavor. We just hope that he brought a toothbrush.