The Lonely Boy from Hoboken: The Early Years of Sinatra


How the only child of two Italian immigrants went from the streets of Hoboken to the bright lights of New York.

Francis Albert Sinatra, around the age of 10, sporting the fedora hat that would become part of his signature look. Source: Biographics

“They had in the bar a piano with a roll in it, you put a nickel in it and played the songs, and occasionally one of the men in the bar would pick me up and put me on and I would sing with the roll. It was a horrendous voice. Terrible. Like a siren… So one day I got a nickel and I said, “This is the racket. This is what you gotta be doing.”” ~ Frank Sinatra recalling his early says singing in “Marty O’Brien’s”

On a frigid December afternoon in 1915, a baby boy weighing more than thirteen pounds was born in a cold water flat in Hoboken, New Jersey. He emerged blue and silent, leading the doctor to place the presumably dead infant next to the kitchen sink so he could focus on saving the young mother, Natalina, better known as “Dolly.” But Dolly’s mother was not ready to cast her grandson aside. She picked up the baby, placed him under freezing cold water, and slapped him until his lungs produced loud cries. It was apparent from that first cry that Francis Albert Sinatra was born to sing.

From the start, Sinatra was plagued by insecurities that he was never able to completely rid himself of. The forceps that were used to deliver him left physical and emotional scars. In his first known photo, the chubby faced baby is shown lying naked on a bear-skin rug, photographed from the right side, the side he would prefer to be photographed from for the rest of his life. The scars that ran from his ear to jawline were easy targets for the tough boys on the streets of Hoboken, who nicknamed the self-conscious boy “Scarface.” Besides the external scars, there was also damage to his eardrum, one of the reasons he was able to escape the draft during World War II.

Sinatra’s First Communion in Hoboken, ca. 1923. Source: Historical Boys’ Clothing

Dolly and her husband Martin Anthony “Marty” Sinatra were both Italian immigrants from large Catholic families, but after Sinatra’s traumatic birth, it was clear there would be no more children. As a result, he and his mother formed a tight bond that lasted until her death in 1978. Although she doted on her son, Dolly was also physically and emotionally hard on the boy, and she made it clear she expected great things from him. His relationship with his father was more gentle, yet cool. Marty was a reserved man who rarely showed emotion, and Sinatra would later admit he spent much of his life seeking praise and approval from his father.

Sinatra’s parents, Marty and Dolly, on their wedding day, February 14, 1914. Source: Sinatra

In the first few years of his son’s life, Marty went from job to job, even taking up boxing and using the Irish pseudonym “Marty O’Brien.” Mastering improper English, he never did learn how to read, but he made sure his son did. With his father working to keep food on the table and his mother being immersed in the local Democratic Party and also serving as a midwife, young Sinatra was left to the care of relatives and close friends during the day. Having never forgotten the loneliness that plagued him during childhood, as an adult, Sinatra had the constant need for someone to be with him.

With the city of Hoboken refusing to enforce the Eighteenth Amendment, Marty and Dolly opened a bar called “Marty O’Brien’s” in the midst of Prohibition. Young Sinatra was known to stand on top of the piano and sing to bring in extra money, and he also saw this as a great way to get extra attention. When the Depression hit, he volunteered to sing on street corners to help his parents stay afloat. It was not Dolly’s dream for her son to become a singer, but once she saw the crowds that gathered, she became his biggest supporter. Sinatra began investing time in perfecting his voice by listening to countless hours of radio and paying close attention to Bing Crosby’s baritone voice.

Marty envisioned his son finishing high school and going to college, but Sinatra was not school material. Less than fifty days after starting high school, he was expelled due to “rowdiness.” His teachers said the boy had no ambition, but that was not true, he had the ambition to sing. While he was in school, Sinatra arranged dances and performed, always receiving rave reviews. While teachers saw him going nowhere, his peers knew he was going somewhere.

A young Sinatra in Hoboken, ca. 1935. Source: Hoboken Historical Museum

With no obligations to school, Sinatra persuaded his parents to let him perform on radio stations in Jersey City. They agreed, so long as he would also get a “real job.” Dolly first landed her son a job as a newspaper delivery boy and then a shipyard riveter. Finally, he was hired by the Union Club where he earned $40 a week.

Since Sinatra had honored his parents’ wishes, he was able to pursue singing. He began what would be the only professional vocal lessons he would ever take with John Quinlan in New York. Quinlan praised Sinatra’s ability, saying he could vocalize to a B-flat on top without the assistance of a microphone.

Sinatra took a couple of nightclub jobs in New Jersey at small joints and performed on a local radio station for free, but he had his eyes set on “The Big Apple.” Crossing the George Washington Bridge to New York City, the ambitious singer took a few low-paying engagements that barely covered food and cigarettes. Finally, a break came in 1935 when Dolly cajoled a local singing group in Hoboken called the The Three Flashes to let her son into the group. Because Sinatra had a car, they agreed, and The Hoboken Four was born. Soon after, the quartet was planning to audition for one of the most popular radio programs on the air, Major Bowes Amateur Hour.

Sinatra (far right) with the “Hoboken Four” appearing with Major Edward Bowes on the “Major Bowes Amateur Hour” in 1935. Source: A Trip Down Memory Lane

The Hoboken Four was a smash hit on Major Bowes; such a success that they took home first prize: a six month contract to appear across the country on radio and stage. Sinatra swiftly became the lead singer in the group. His success and popularity, especially with the opposite sex, caused strife in the group, and the tension become so rife that he was regularly beaten by his cohorts. Deciding he had enough of the abuse, he quit half-way through the contract.

With his unbridling ambition, Sinatra took a job as a singing waiter at a roadhouse called the “Rustic Cabin” in New Jersey. Earning $15 a week, he was introduced to WNEW radio station and was asked to perform live on Dance Parade for fifteen minutes every night with a group from the “Rustic Cabin.” Seeing this as the biggest thing that had happened to him, Sinatra told friends he was rising so high to fame that “no one could touch him.” Marty, who had referred to his son as a “bum” after dropping out of school, was now a proud father.

Sinatra and his first wife, Nancy Barbato, on their wedding day at Our Lady of Sorrows Church in Jersey City, New Jersey. The marriage would last from 1939-1951 and produce three children. Source: Sinatra

Singing on WNEW, Sinatra was capturing the hearts of young couples enwrapped in blooming romances, and he too was in-love. On February 4, 1939, the twenty-three-year-old married an attractive, petite Italian-American Catholic named Nancy Barbato. The next month, one of his friends from a New Jersey radio station, a saxophone player named Frank Mane, arranged for Sinatra to record a song called “Our Love.” He was finally a solo artist.

With Sinatra making a steady $15 a week and Nancy $22 as a secretary, the couple were barely getting by. But the tide shifted one night in June after bandleader Harry James approached Sinatra and asked if he would join his band at $75 a week. Sinatra said he would leave with the band that night! The Harry James Band hit the road touring and one by one Sinatra’s records were released. The first to be released in July 1939 was “From the Bottom of My Heart,” followed by “All or Nothing At All;” both received little acclaim at the time.

Sinatra was getting by with the Harry James Band, but he was yearning for more. In the fall of 1939, with Nancy pregnant with their first child, Sinatra concluded that there was no way he could surpass his idol Bing Crosby by remaining with the Harry James Band. So when Jack Leonard, the lead singer for the Tommy Dorsey Band, told Sinatra he was leaving the group, he unhesitatingly jumped at the opportunity. Harry James had no choice but to let the ambitious young crooner out of his contract.

Joining the female lead singer Jo Stafford and the other boys of the band, Sinatra was again the odd man out. Jo Stafford recalled the first time she saw Sinatra, “Out on the stage walked this very skinny, unprepossessing young man, and I thought, “Wow!”” But inside that skinny young man was a voice whose range was continuing to grow, and as Stafford said, they knew they were hearing something unique.

A twenty-four-year-old Sinatra performing with Tommy Dorsey, the most popular bandleader during the “Big Swing” era. Source: WNYC

Sinatra gained a father-figure in Tommy Dorsey, a man whom he emulated and admittedly feared, and there were tensions amongst band members, but Sinatra knew the success he had longed for was finally within reach. The crowds were no longer coming to hear Tommy Dorsey, they were there to see Sinatra. The lonely boy from Hoboken, who began his career singing on top of a bar, was playing with the hottest band in the country, performing to packed houses everywhere, and, in 1944, he would be the cause of one of the largest riots “The Big Apple” had ever seen. Sinatra had arrived.

To learn more about Frank Sinatra and his hometown of Hoboken, visit the Hoboken Historical Museum.

The 2015 documentary “All or Nothing At All” also goes in-depth look into Sinatra’s childhood and early career.



Holley Snaith | Follow Along #HistorywithHolley
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Holley is a published historian specializing in 20th century history. Visit to learn more.