10 Restaurants Frank Sinatra Used To Frequent

Frank Sinatra died in 1998, but his legend endures well into the 21st century. The king of crooners was known for more than his smooth, expressive voice. In many ways, Sinatra embodied the sophisticated nightlife culture of the 1950s and '60s, frequenting all the hotspots with his famous friends, who ranged from movie stars and Kennedys to mob kingpins, big-time bookies, and, of course, his squad: the Rat Pack. He had a bottomless appetite for life, and for the food and drink that are among the things that make life worth living.

Sinatra may have had a string of wives and girlfriends, but once the Chairman of the Board found a restaurant he loved, he was devoted. The spots didn't have to be fancy, either. He was an Italian-American kid from the streets of Hoboken, and he appreciated a relaxed neighborhood joint as much as a lavish spread at a Las Vegas steakhouse. If the food and the company were good and he could eat unbothered, that worked for Frank. He'd be back again and again, befriending not only the owner but the service staff, whom he always tipped extravagantly. 

Rather than exploring the local food scenes during his travels Anthony Bourdain-style, Sinatra returned often to his favorite hangouts, sat in his favorite booths, and ordered his favorite foods. Here are some of Old Blue Eye's tried-and-true eating establishments, starting with his hometown and ending up in Rat Pack stomping grounds, Las Vegas.

If you're in the Hoboken area and feel like walking in Sinatra's shoes, stop in at this restaurant founded by Sinatra's childhood friend. Leo's Grandevous has been serving authentic Italian food since 1939. That's when newlyweds Leo and Tessie DeTerlizzi, who lived upstairs, took over the place. In an interview with The Hoboken Girl, their granddaughter and current co-owner Grace Sciancalepore, "It was a pool hall where people played cards and hung out at the bar. When Grandpa took over, he turned it into more of a restaurant and Grandma did all the cooking." It remains a genuine family business, with many of Tessie and Leo's recipes still on the menu.

In the early days, Frank and his band would stop in after gigs for a late-night bite. Sinatra liked "Leo's Famous Mussels" with red sauce, although they were probably not 'famous' back then. The bar area has been renovated since Sinatra last dropped in, but it's overall still the same, and the jukebox plays all-Sinatra, all the time. Sinatra photos and posters line the walls. As for the menu? It's full of Italian classics.

Leo's offers a full complement of antipasti alongside a mouth-watering list of pastas. Veal, shrimp, and chicken offerings round out the entrees, and there are plenty of bar pie options — gluten-free included, as well as sandwiches — parmigiana and otherwise. Finally, there's a rotating daily special; we're especially intrigued by "Tessie's Famous Stuffed Calamari." 

https://www.leosgrandevous.com/

(201) 659-9467

200 Grand Street, Hoboken, NJ 07030

Patsy's is a family-owned Neapolitan restaurant where tradition runs deep. Pasquale "Patsy" Scognamillo opened the place in 1944, and, in the 80 years since, Patsy's has had only three chefs: Patsy, his son, and now his grandson, Sal Scognamillo, who still buys from the same vendors who once sold to his grandfather.

Sinatra first met Patsy when bandleader Tommy Dorsey brought him in. Patsy and Frank worked diligently on that project. Sinatra's table was upstairs in the back, and his favorite dish was clams Posillipo. Patsy made Frank a bespoke version; aware that the singer didn't like heavy garlic, he'd sauté the cloves, remove them, then finish the recipe. Even now, Patsy's remains as devoted to Sinatra as he was to Patsy's; they serve his favorite dishes every year on his birthday. Diners start with the clams, followed by fusilli with fileto di pomodoro, and finish with ricotta torte. If that doesn't make your mouth water, Sinatra also loved the veal milanese, which Patsy would pound until it was paper-thin. Finally, there are a number of Patsy's restaurants in Manhattan, but, where Sinatra — and fine dining — are concerned, there's only one, and it's located on West 56th Street between 7th and 8th Avenue. 

https://www.patsys.com/

(212) 247-3491

236 W. 56th St., New York, NY 10019

Some say Jilly's Saloon, not Patsy's, was Sinatra's favorite Manhattan restaurant. The flashy, crowded Jilly's was Patsy's polar opposite in all things but protecting Sinatra's privacy. Jilly's was owned by Jilly Rizzo, a minor celebrity, likely small-time gangster, and, most importantly, Frank's closest friend. Rizzo was Italian-American, but his restaurant served Cantonese food, albeit what sounds like the Americanized version of the 1960s: chicken or shrimp chow mein and moo goo guy pan. Whether the mispelling of 'gai' was an intentional nod to testosterone, a Freudian misprint, or lost in translation is a mystery. Chef Howie was Chinese, though, and Jilly's regulars were reportedly huge fans of his BBQ pork.

Frank had two wooden blue armchairs at the back, against the wall. No one else could sit there, and when Sinatra left town, those chairs went to storage until his return. According to reporter Gay Talese in his article "Frank Sinatra Has a Cold," Jilly's was the place where Sinatra's friends, admirers, and maybe-acquaintances gathered to pay their respects or to catch a glimpse of their idol. For their part, the staff operated as defensive lineman, blocking their charge so he could have a moment of fun or relative peace.

In 1986, the space was taken over by the Russian Samovar, another popular celeb hangout. In homage to the spot's Rat Pack roots, the new owners kept the original red banquettes and bar.

https://russiansamovar.com/

(212) 757-0168

256 W. 52 St., New York, NY 10019

The 21 Club was a clubhouse for the wealthy or uber-interesting, and the building remains an NYC icon. The Bar Room featured a weirdly playful, possibly priceless, nod to its corporate and political overlord clientele: A literal mass of toys hung from the ceiling, donated by sports figures, presidents, and CEOs. The prices were gobsmacking. Still, 21 was power lunch central. You were paying for the history. After 98 years, the restaurant fell to the COVID-19 pandemic, but its 37 cast-iron lawn jockeys continue to stand guard over 52nd Street. 

Sinatra must have enjoyed the edge of danger permeating this former speakeasy, which was riddled with secret passages. In 1962, importation of Cuban cigars was about to be banned, so the owners loaded 750,000 Havanas and kept them on hand for their favorite customers. Sinatra was one of these, and management made all kinds of special accommodations for him. According to former 21 manager Bruce Snyder in an interview with the New York Post, "Sinatra liked these red cherry peppers that came in a jar at the supermarket. We left [them] in the refrigerator for him. He enjoyed drinking Sambuca Originale, which was not the best sambuca. You couldn't find it in the Manhattan liquor stores. So we had to bring it in from New Jersey.". That Sambuca paired well with Sinatra's go-to steak order and, of course, his gallon jar of grocery store cherry peppers.

Permanently Closed:
https://www.21club.com/

(212) 582-7200

21 West 52nd Street, New York, NY 10019

Veniero's is still an East Village institution, and people in the know travel way downtown just to pick up cannolis, Yule logs, rainbow cookies, rugelach — everyone has their favorite. Sinatra's go-to order was the Biscotti Regina, a not-too-sweet sesame cookie that, unlike regular biscotti, is baked just once, though Sinatra would only eat them if they were a little burnt, so he'd get a bespoke batch. According to current owner Robert Zerilli in an interview with the New York Post, "We shipped Sinatra big boxes to his house in Palm Springs. We have his autographed picture in the store, it says, 'I love your pastries, but you're killing me.'" FYI: Biscotti Regina are extremely dunkable. 

Veniero's is the oldest still-operating business on this list. Italian immigrant Antonio Veneiro bought the building and opened a confectionery/pool hall in 1894, back when ice was delivered by horse cart, and the pastries were baked in a backyard coal oven. It must have worked, because 130 years later, Veneiro's is still turning out pastry around the clock in its basement bake shop. Perhaps the most important thing to note is that you don't have to be rich, famous, or anything else to feast on Veniero's handmade delicacies. They shipped to Sinatra, and they'll ship to you. The hard part might be deciding what to order. Or maybe figuring out how not to eat it all as soon as it arrives.

https://venieros.com/

(212) 674-7264

342 East 11th St., New York, NY 10003

Chicago was, in Sinatra's words, "My kind of town." And Old Town's Twin Anchors was his kind of restaurant: a low-key local tavern that's been around since 1932. The building dates to the 1880s, and the first tavern on site opened during Prohibition. From the outside, it was a soda fountain named Tante Lee's Soft Drinks, but there was a secret door leading to a speakeasy. Frank first came to Twin Anchors in the 1950s. As he got more famous, the owners would shut the place down while Frank and his friends ate, and on the way out the door, he'd tip everybody a cool hundred bucks.

When we say Twin Anchors is low-key, co-owner Mary Kay Tuzi admited to WGNTV, "It either looks like a Wisconsin bar, or my grandmother's basement." It's not about the surroundings, though; it's about those fall-off-the-bone baby back ribs. Sinatra's standing order was: "Ribs and keep 'em coming" according to Twin Anchors Ribs. His patronage put Twin Anchors on the map, and, once again, the restaurant gave him special treatment, installing a private phone line just for him, with a jack beside his favorite table, in case he was expecting a call.

But if you're hanging at Twin Anchors, be warned: Ever since the disco era, there's "Positively No Dancing." Dancers versus servers with massive slabs of baby back ribs was a messy combination.

https://www.twinanchorsribs.com/

(312) 266-1616

1655 N. Sedgewick St., Chicago, IL 60614

Since 1919, Musso's, as regulars call Musso & Frank's Grill, has been dealmaking central. The original payphone — the first public pay phone in Hollywood — is still there, although disconnected. If phone booths could talk... 

Musso's is as old school as they come, and the public is there for it. Even Taylor Swift has a favorite booth, although the waitstaff is tight-lipped about which one. Of that predominantly male waitstaff, many have worked at Musso's for 30 years or more. The red tux jacket-clad squadron treats everyone with respect, especially their regulars. These included Sinatra, who liked high-walled booth 224 in Musso's 'new room,' which should perhaps be called the 'newer' or 'newest' room; it opened in 1955. 

The 'old room' is a time capsule, complete with original wood paneling and deeply-faded English manor-core wallpaper. Current CEO Mark Echeverria explained to Afar, "Humphrey Bogart's cigar smoke is up there. How could I possibly take down that paper?" And the menu? If you want to eat like Sinatra, you go simple: filet mignon and two fingers of Jack Daniels, three rocks, and a splash of water. If you want to eat like Charlie Chaplin, you can do that, too, but you'll be having grilled lamb kidneys with bacon. The rotating daily specials include corned beef and cabbage, chicken pot pie, and sauerbraten with potato pancakes. Apparently, old Hollywood ate heavy, with a nod to their immigrant roots.

https://mussoandfrank.com/

(323) 467-7788

6667 Hollywood Blvd., Hollywood, CA 90028

The Sinatra-era supper club is not to be confused with the Midwest supper club, despite the name. In the 1950s and '60s, supper clubs were elegant restaurant/nightclubs, the kind you might see in a Fred Astaire/Ginger Rogers movie. They were places where fancy people came to gossip, drink, listen to jazz or a big band, and glide across the dance floor. That's the best-case scenario, anyway.

The Rat Pack frequented any number of these establishments, but the iconic Palm Springs Purple Room, located in the Club Trinidad Hotel, still exists. Back in the day, Sinatra, Dean Martin, and Sammy Davis Jr. all owned homes nearby. They'd stop in for drinks or dinner, and sometimes take the stage — unannounced and unpromoted, pop-up Rat Pack-style. 

The club's origin story, including the founder's name, has been forgotten. Was this just poor record-keeping or an extralegal muddying of the books? Who can (or will) say? However, the Sinatra connection is well-documented. According to Art Brigman, former manager of the Purple Room in an interview with Palm Springs Life, "Sinatra loved to perform here. Frank would drive into Palm Springs so we'd get him going in and going out. He liked to patronize The Purple Room. He called it a saloon. He said he was a saloon singer and loved to hang out in saloons." Sinatra's granddaughter, singer A.J. Lambert, played The Purple Room for Frank's 100th birthday celebration.

https://www.purpleroompalmsprings.com/

(760) 322-4422

1900 E. Palm Canyon Dr., Palm Springs, CA 92264

When in Vegas and craving Italian food, Sinatra went to Piero's, an old-school Italian restaurant, complete with curved leather booths and white tablecloths. Piero's — which opened in 1982 — might look familiar if you've seen Martin Scorsese's 1995 mob movie, "Casino." The film was fictionalized, but Piero's role in American mobster history is real. In 2005, the dining room was the site of a major bust, courtesy of the FBI and DEA. They arrested a pair of NYPD detectives out on the town. The charge? Aiding and abetting eight murders on behalf of the Lucchesi crime family. In the Swiss tradition, Piero welcomed diners on both sides of the law. According to the former proprietor, Freddie Glusman, a mobster once asked him to take a picture of the Kennedy brothers off the wall because he hated them so much. Did Glusman oblige? Probably. An angry mobster's version of a bad Yelp review could prove fatal.

Frank's go-to order was the linguini and clams; he'd take some for the plane on his way out of town. That recipe has never changed. Unsurprisingly, Piero's has a reputation for protecting the celebrities who eat there. Evan Glusman, son of the owner, explained to Neon, "This is kind of like Switzerland. People feel safe here." No wonder Sinatra kept coming back.

https://www.pieroscuisine.com/

(702) 369-2305

355 Convention Center Dr., Las Vegas, NV 89109

Meet Frank Sinatra's go-to steakhouse in Vegas: The Golden Steer. Founded in 1958, this steakhouse was on the right side of history. According to the owner, Dr. Michael Signorelli, Sammy Davis Jr. introduced Frank to the place. It was the '60s, and African-Americans were barred from eating at the hotel restaurants, even if they were headlining the room. The Golden Steer, though, was happy for Sammy's business, and, soon enough, Sinatra, too, had a preferred table: "table 22," a four-top.

The Golden Steer hasn't changed much since Sinatra's day. That goes for the decor — white tablecloths and the requisite circular leather banquettes — as well as the service. The servers wear tuxedos, make tableside Caesar salads, and light retro classics like bananas foster and cherries jubilee on fire without melting anyone's false eyelashes. (Admittedly, the eyelash thing is pure and irresistible editorial assumption.) 

As for the menu, if you want to eat like the Chairman of the Board, you absolutely still can. His favorite dish was the relatively economical steak pizzaiola. But for a month in 2015, in honor of his birthday, the Steer offered "Frank's Menu," a 3-course prix fixe dinner that included seating in booth 22. The meal opened with clams casino, followed by a 16-ounce, medium-rare New York Strip (accompanied by Jack Daniels), and, to bring the meal home: bananas foster, aflame.

https://goldensteer.com/

(702) 384-4470

308 W. Sahara Ave., Las Vegas, NV 89102