Francis Albert Sinatra (1915 – 1998)

For a virtual version of the Museum’s Sinatra Walking Tour map, click here.

Old Blue Eyes. The Voice. Chairman of the Board. Or, in Hoboken, simply “Frankie.”

Frank Sinatra is Hoboken’s most famous son. Though the talented singer moved out of town after he achieved fame, his Hoboken upbringing shaped his early career and imparted a cocky but relatable image, which helped make him an icon. The trajectory of his family’s life in Hoboken reflected the opportunities and divisions in early twentieth century urban America.

He was, as one writer put it, “a kid from Hoboken who got the breaks.” And in the course of his sixty-year career, that skinny kid the others called “Slats” reshaped American popular music and ideas about style.

Frank Sinatra was America’s first teen heartthrob, earning another nickname – “Swoonatra” – after girls started fainting at his concerts during the 1940s. Boys imitated his slicked-back hair and cocky demeanor. All across the country – and then the world – sighing, swooning, swaggering fans fell in love with that voice, with an intimate style of singing that brought the listener inside the song, alongside the singer.

  • Album cover, Frankie and Tommy. Full record.

Perhaps that is why former bobby-soxers and zoot-suiters – sometimes with their kids and grandkids in tow – have journeyed for years to Sinatra’s birthplace, or packed into local taverns to celebrate the birth of this city’s most famous native son. Younger fans mention the Rat Pack and the Chairman’s cool, but many also cite his musical artistry as inspiration.

And when the news broke on May 14, 1998, that Frank Sinatra had died, the fans came again to Hoboken, to pay respects and to mourn. The bronze star the Hoboken Historical Museum had installed at the singer’s birthplace two years before was soon surrounded by candles, handmade signs, flowers, notes, photographs, and even a loaf of coal-fired oven bread, a Hoboken specialty that the singer sometimes had shipped to California.

Francis Albert Sinatra was born on December 12, 1915. Frank, who was an only child, lived at 415 Monroe Street until he was twelve years old. His mother, “Dolly,” whose maiden name was Natalie Della Garavente, was a midwife and ward leader during her years on Monroe Street. His father, Anthony Martin Sinatra, was a boxer who, though born in Sicily, went by the name of “Marty O’Brien” in order to be allowed to fight in Hoboken’s Irish-only gymnasiums. Marty later became a tavern-owner and firefighter.

The four-story, eight-family, wood-frame, cold-water apartment house of Sinatra’s youth no longer exists. After a major fire in 1967, the building was seized by the city and demolished a year later. In 1996, the Hoboken Historical Museum designed and installed a 3-foot-square bronze plaque in the sidewalk commemorating Sinatra’s birthplace.

Writer Pete Hamill noted in a tribute to Sinatra that when the singer’s career began, “there was an America that now doesn’t exist very much, a kind of blue-collar America, industrial America… and nobody had represented that before.” Sinatra could easily summon images from working-class, urban life. In his neighborhood, he told a radio audience in 1980, boys became fighters or they worked in factories. And Sinatra knew more than a little about street-tough guys, from spending time in smoky nightspots like the Cat’s Meow – one of nearly 200 social clubs in the city during the thirties. Today, about a half-dozen remain.

And yet, Frank’s growing-up years weren’t nearly as rough as some biographies have suggested. He was a rare only child, in a family whose fortunes increased through his mother’s savvy political connections. In fact, one of young Frank’s other nicknames, “Slacksy O’Brien,” stemmed from his family’s ability to buy him so many pairs of dressy pants. Although it’s certainly true that Frank was born in a cold-water flat, many immigrant families made homes in such apartments. And the Sinatras, after all, did not remain on Monroe Street for long.

As a third ward leader, Frank’s mother Dolly was a significant cog in the city’s political machine, gaining Democratic votes for higher-ups and dispensing and gaining favors. Like most Hoboken residents, she was aware of the division of power – and the city – between the Irish and Italians, but her close involvement with those in power allowed her to literally cross those lines. In 1920s Hoboken, Italians didn’t dare cross Willow Avenue, a kind of dividing line between the Italian and Irish neighborhoods; and yet, the Sinatras – sometimes calling themselves “the O’Briens” – moved across Willow, and then moved again, each time closer to the prestigious Irish/German section of town.

The Hoboken of the 1920s and 1930s was also a city bursting with younger singers, who performed on street corners, in clubs, in private homes, and in pool rooms – wherever they could get an audience.

Young Frank’s usual haunts included his father’s bar, Marty O’Brien’s at 333 Jefferson Street; the Crystal Ballroom, at 530 Jefferson St., now a condo building; and Tutty’s Bar, at Sixth and Adams Streets. The Cat’s Meow, at 604 Grand Street, not only offered him a stage, but also an occasional opportunity to sleep under the pool table when he wanted to get away from his mother. As his confidence and skill improved, he snagged a $40/week gig at Hoboken’s popular Union Club (600 Hudson St.), for dances and banquets. The Union Club was one of the first successful banquet halls owned by the upwardly mobile Italians who were making Hoboken their own, as Paul Samperi describes in one of the Museum’s Oral History chapbooks, A Fine Tavern.

 In September 1935 Sinatra joined up with a Hoboken trio, The Three Flashes, to form the Hoboken Four. They sang on the nationally broadcast radio show, Major Bowes and His Original Amateur Hour, and were voted its most popular act.

The group toured the country for several months, then Sinatra went solo, singing at dances at Hoboken clubs, until he got a gig at the Rustic Cabin in Englewood Cliffs. Bandleader Harry James heard Sinatra on a WNEW Dance Parade broadcast from the Cabin and offered him a position as a vocalist. In late 1939, he joined the Tommy Dorsey band.

When Dorsey’s lead singer quit the band, Frankie and Tommy became a popular musical duo before Sinatra left in 1943 to embark on a hugely successful solo career. Though his later career had ups and downs, he would record hit songs and star in movies for decades.

But by the early 1940s, Frank had already left Hoboken. He married his sweetheart Nancy Barbato, whom he met at the Jersey Shore, and moved into Jersey City before relocating to California. Marty and Dolly remained in Hoboken, finally settling in a grand house at 909 Hudson Street that Frank had bought for them.

In 1947 Frank Sinatra made his last public appearance in the city for nearly forty years – until he returned to accompany Ronald Reagan to St. Ann’s Feast in 1984. On October 30, 1947, Hoboken celebrated Sinatra Day, the final event in a month-long March of Progress celebration orchestrated by Mayor Fred M. DeSapio with the assistance of his dedicated ward leader, Dolly Sinatra. Twenty thousand people lined Washington Street in the pouring rain to catch a glimpse of the star, who announced, “I’ve met people in cities all over the country, but folks here in Hoboken, well, they’re just wonderful – that’s all.”

More than a few Hobokenites will return the compliment. As one man wrote to “Blue Eyes” in the sign-in book at Sinatra’s birthplace: “I was much younger than you, but grew up in this town, and all my family knew you and your legacy growing up here. Thanks for the world.” Hoboken has thanked Frank Sinatra by dedicating its main post office, a waterfront park, and a street along its picturesque waterfront, to the city’s most famous son.

Sinatra’s fans inspired the Museum to create a Sinatra Walking Tour map. You can begin the tour by picking up a copy at the Museum at 1301 Hudson Street. As you take the tour, note the changing architecture of each Sinatra family home. You may gain a sense of what life was like here during the singer’s early years – and what remains from that time. Imagine the life of a teenaged Sinatra and his family, and also the long-vanished social clubs, pool halls, and bars of the thirties, where Frank and his contemporaries sang

The Museum also dedicated an issue of its magazine, Hoboken History, to the singer and his changing relationship with the Mile Square City. You can download a pdf version of the file from our collections.

In addition to the materials featured above, the Museum also has a large collection of Sinatra memorabilia in our digital collections.

–Edited by Darian Worden

Drawn from the following sources: Sinatra Tour Map text by Holly Metz, Hoboken Historical Museum, 1998, as well as “Frank Sinatra Sang Here…,” by Melissa Abernathy, July 22, 2013, in hMAG, and Frank Sinatra Biography, Rolling Stone magazine.

Thank you for visiting our page. Come visit us at 1301 Hudson Street for changing exhibits about Hoboken’s rich and varied history.