“When I was there, I just wanted to get the hell out,” Sinatra once said of the town where he was born.  “It took me a long time to realize how much of it I took with me.”

Of course, much of Sinatra’s Hoboken has disappeared over the years.  During the past two decades, Hoboken has become a popular destination for New York professionals looking to take advantage of cheaper real estate off the island of Manhattan.  It’s been gentrified, yuppified and trendified, sometimes to the dismay of longtime residents in what used to be a solidly working-class town of immigrants.

But underneath it all, Hoboken is still the town of Sinatra’s birth, the tough, lively town made by its docks and its taverns, transformed by World War I and then subject to a rocky history as shipping companies and industry went elsewhere.

It’s smaller now—around 40,000, as opposed to the 67,611 inhabitants recorded in the year of Sinatra’s birth—but it still occupies that single square mile north of Jersey City and south of Union City, directly across the Hudson from Chelsea and the West Village.

And it is still the town that had a powerful influence on the man Sinatra turned out to be.

“Hoboken was a tough place,” said longtime resident Judge Charles DeFazio in the “Circus Maximus” chapbook, part of Vanishing Hoboken: The Hoboken Oral History Project, an undertaking of the Hoboken Historical Museum and the Friends of the Hoboken Public Library.   “You couldn’t be a Pollyanna and live here.  You had to be able to hold your ground.”

The young Sinatra wasn’t a Pollyanna, though he may have looked it in the fedoras and stylish slacks he wore from a tender age.  His grandparents had come to America from Sicily, settling in the New Jersey town that was increasingly divided between German, Irish and Italian immigrants.  When Sinatra was born in 1915, those groups still lived in their own neighborhoods, shopped in their own stores, attended their own churches, and mixed reluctantly.  Fights were common, and street gangs flourished.

The Germans occupied the most affluent areas of town.  The Irish were next on the social totem pole, with Hoboken’s Irish community famously supplying New York City with much of its police force.  The Italians, at the time Sinatra was born, lived in the poorest areas of town.

Sinatra absorbed a few beatings when he walked through the wrong neighborhoods—although as his family’s fortunes improved, they moved into more affluent areas of town.  He also heard plenty of ethnic slurs, to the point where the racial tensions and name-calling in the town, he later said, “rubbed me the wrong way.”

In a radio interview, Sinatra once identified the two avenues he saw as most open to youngsters in Hoboken: You either became a fighter, or you went to work in a factory.  But the town had attracted people, and grown to the size it was at the turn of the 20th Century, because of its importance as a hub both for the railroads and the trans-Atlantic shipping lines.

Several large shipping companies used Hoboken as their base to bring in goods and immigrants from Europe.  On land, meanwhile, the Delaware, Lackawanna and Western Railroads all established terminals in Hoboken, from which their passengers would then catch ferries across the Hudson to New York City.

By the time of Sinatra’s birth, Hoboken had grown from 7,000 people to almost 70,000 in little more than half a century. Almost two-thirds of the inhabitants were born in the United States; of the recent immigrants, slightly more were German than Italian.

But World War I, which ended before Sinatra turned five, changed the city’s ethnic makeup.  During the war, some Germans were forcibly relocated, while parts of the city were put under martial law.  Piers owned by the Hamburg-American Line were seized by the government and used as a port of embarkation for more than three million soldiers heading to Europe.  General John J. Pershing, leader of the American Expeditionary Force in the war, coined a battle cry for soldiers hoping for a swift end to the conflict: “Heaven, hell or Hoboken…by Christmas!”

Sinatra came of age in the aftermath of the war, when the city was still tough, hard-drinking (even during Prohibition) and working-class, bound by big families and strong traditions.   His father worked on the docks, fought for money, and spent a long time in the Hoboken Fire Department; his mother, by all accounts a force of nature in the town, worked as a midwife and a Democratic party committeewoman, among other things.

In Pete Hamill’s book Why Sinatra Matters, the author suggests that Hoboken’s tight-knit Italian community taught Sinatra the importance of loyalty to family and friends.  In Hoboken, Hamill writes, the young Sinatra was immersed in “a world of feasts, weddings, funerals, and celebration,” a world long on tradition and honor.  At the same time, though, he says Sinatra was lured by the influences of the new country rather than the old: “baseball, the Fourth of July, the vistas of the American deserts that were shown in westerns at the movie house….”

Music, soon to be Sinatra’s passion, was in every home; with the advent of Victrolas, which were first mass-marketed in the year of his birth, professional singers acquired a whole new way of being heard.  When Sinatra was six, WJZ in Newark began regular radio broadcasts. And the movies—silents at first, talkies before Sinatra was 15—were easily accessible as well.

Sinatra started imitating movie stars and radio comics in junior high, and singing publicly during his brief stint at A.J. Demarest High School.  He worked on the shipyards for a few days, and unloaded crates of books for slightly longer.  He talked about becoming an engineer and studying at the city’s prestigious Stevens Institute of Technology—but in the end, with the support of his mother and to the dismay of his father, he opted to try his hand at music instead.

He was not alone in this. “The Hoboken of the 1920s and ‘30s,” says a tour guide published by the Hoboken Historical Museum, “was…a city bursting with young singers, who performed on street corners, in clubs in private homes, and in pool rooms—wherever they could get an audience.”

For live music, Hoboken also had “social clubs,” taverns and saloons and smoky nightspots and private rooms that might put a singer in the corner or on a small stage.  There were as many as 200 such establishments in the city in the 1930s.

By the time he was 20, Sinatra was performing for $40 a week at the Union Club, which had been a German private club called the Deutscher Club until World War I’s anti-German sentiment had forced a name change.

And then, before long, he was gone.  He appeared on the Major Bowes and His Original Amateur Hour radio broadcast (with a group called the Hoboken Four), he got married in Jersey City, he moved out of Hoboken, he landed gigs with Harry James and then Tommy Dorsey…and, in a way, he never looked back.

Except that sometimes he did look back.  When he was a star, he returned to his old high school, spoke, and then sang a few songs a capella, because he didn’t have a band but the students demanded it.  He later got a high school diploma, and an honorary doctorate from Stevens Institute, and a street named after him.

And he almost came back to star in the movie that immortalized the Hoboken docks where he’d briefly worked decades before.  Director Elia Kazan initially wanted Sinatra to play the lead in On the Waterfront, going so far as to make a deal that was scuttled when producer Sam Spiegel set his sights on a different actor.

“I knew—and believe now—that I could make the picture with Frank and that he’d be fine in the role,” wrote Kazan in his autobiography, A Life.  In the end, though, it was Marlon Brando who stepped in and won an Oscar for playing the Hoboken bum who “coulda been a contender.”

Sinatra was heartbroken, but he went on with a pretty fair career of his own.  And, in a way, he didn’t need to play a guy from Hoboken onscreen; he played that guy every day.

Pat Spaccavento of Piccolo's restaurant, a Hoboken fixture and Sinatra shrine, summed it up to the Star-Ledger after Sinatra’s death. "He was a Hobokenite,” said Spaccavento, “in a way no one who's not a Hobokenite can ever understand."