Surprising Tidbits You Didn’t Know About Frank Sinatra

He was one of the best-selling music artists of all time, selling more than 150 million records worldwide including “Strangers in the Night,” "Love and Marriage," "New York, New York” and “My Way.” But his beginnings were humble. He was born at home in his parents’ Hoboken, New Jersey, apartment on December 12, 1915. He became one of the most popular and influential musical artists of the mid-20th century – Frankie, “Ol’ Blue Eyes,” “the Chairman of the Board” – Frank Sinatra.

Although you know his music, you probably didn’t know he was heavily involved in politics, campaigning enthusiastically for presidents Harry Truman, John F. Kennedy and Ronald Reagan. Right around the time of JFK's death, rumors begin swirling about Sinatra’s alleged Mafia connections – and he was snubbed by a decade of politicians until Reagan embraced him. They had been friends in Hollywood.

He almost didn’t survive his birth. After hours of labor, he was blue and not breathing when finally delivered with forceps. Thought to be stillborn, he was laid aside in the kitchen while the doctor worked to save his mother, Natalina "Dolly" Sinatra. His grandmother picked him up and thought she sensed life. She held him under the kitchen sink’s cold running water and, sure enough, he cried out in protest – wailing his first notes.

The O’Briens

His mother Dolly loved politics – volunteering as the leader of Hoboken’s Democratic third ward, where she became a significant cog in the corrupt local political machine. She gained Democratic votes for higher-ups and didn’t shrink from dispensing and gaining favors. There was a sharp divide between Hoboken’s Irish and Italians – newly arrived Italians didn’t dare cross Willow Avenue. However, the Sinatras did – calling themselves “the O’Briens.” They moved across Willow, and then moved repeatedly, each time getting closer to the more respectable neighborhoods. At school, Frank went by “Slats O’Brien.” Due to his love for dress pants, it morphed into “Slacksy O’Brien.”

High School Dropout

He never learned to read music. Dropping out of high school, yearning to become a singer, he delivered Jersey Observer newspapers and worked as a riveter at the Tietjen & Lang shipyard while performing at night at Hoboken clubs such as The Cat's Meow and The Comedy Club. He’d sing for his supper or for cigarettes anywhere they’d give him a microphone – even for free on Jersey City’s radio station WAAT.

In 1935, Dolly talked a local jazz group, the Three Flashes, to let him join. Baritone Fred Tamburro later told a Sinatra biographer that they only took him on because he owned a car and could drive them to gigs. They became the Hoboken Four and appeared on a popular amateur hour show, winning a six-month contract to go on tour in live concerts and on local radio. The talent show’s host, Major Bowes, brought them back repeatedly although it violated his rules – disguising them as "the Seacaucus Cockamamies" and "The Bayonne Bacalas."

The Hits Begin

Tired of the road, young Sinatra got a job as a singing waiter at a roadhouse called "The Rustic Cabin" in Englewood Cliffs, New Jersey, at $15 a week plus tips and sang for free on New York City’s WNEW radio’s Dance Parade. There he cut his first record, “Our Love” at the urging of saxophonist buddy Frank Mane. Only one copy was made. Mane scrawled "Frank Sinatra" on the label and kept it in a drawer for years, finally in 1979 giving Sinatra a copy on a cassette tape. In 2006, Mane's widow sold the recording on eBay through Gurnsey's auction house in New York for $14,000.

About the same time, Sinatra impressed famous bandleader Harry James, who helped him cut his first professional record "From the Bottom of My Heart," which was a moderate hit, followed by "All or Nothing At All,” "My Buddy" and "Willow Weep for Me."

Big-band leader Tommy Dorsey wooed Sinatra away from James’ band for $125 a week and on January 26, 1940, Sinatra opened their show in front of thousands of shrieking teenage girls. "You could almost feel the excitement coming up out of the crowds when the kid stood up to sing,” Dorsey would recall. “Remember, he was no matinée idol. He was just a skinny skid with big ears. I used to stand there so amazed I'd almost forget to take my own solos."

Crazed Teenie-Boppers

The “Sinatra riots” spread. Screaming, adoring teenage girls became hysterical at the first notes of his “I’ll Never Smile Again.” Called “Bobbysoxers” for their rolled-to-the-ankle white socks, the girls swooned in the aisles, creating a new audience for popular music marketing. Sponsors were astonished at the vast economic buying power of teenagers after years of aiming their programming at 30-to-50-year-olds.

When Sinatra appeared New York city’s Paramount Theater on December 30,1942, the shrieking, screaming Bobbysoxers startled host Jack Benny. As Sinatra walked on stage, “The sound that greeted me,” Frank recalled, “was absolutely deafening. It was a tremendous roar. Five thousand stamping, yelling, screaming, applauding. I was scared stiff. I couldn’t move a muscle. Band leader Benny Goodman froze, too. He was so scared he turned around, looked at the audience and said, ‘What the h--- is that?’ I burst out laughing.” The girls screamed in delight, some fainting in ecstasy, the crowd spilling over into Times Square, snarling traffic.

Every Girl’s Dream

During and just after World War II, Sinatra recorded 17 Top 10 singles. The mobs of Bobbysoxer girls earned him such nicknames as "The Voice" and "The Sultan of Swoon." "It was the war years, and there was a great loneliness," recalled Sinatra – since millions of young men were fighting in Europe and the Pacific. Sinatra was unfit for military service due to his eardrum punctured at birth. He became every girl’s dream. "I was the boy in every corner drugstore who'd gone off, drafted to the war."

But after the war, his career stalled and he turned to Las Vegas. There he became one of its most popular attractions as part of a group the media called “the Rat Pack,” which included Dean Martin, Joey Bishop and the black singer Sammy Davis Jr.

Frank detested the color barrier – racial biases which denied Davis the audiences he deserved – and went out of his way to be seen with the talented singer. Movie star Lauren Bacall, with whom Sinatra had a highly publicized affair, coined the term “Rat Pack” – although Sinatra and friends called themselves “The Summit.” They referred to Bacall as their “Den Mother.”

Only the Lonely

Frank won an Academy Award his acting in the movie “From Here to Eternity” and went on to appear in “The Manchurian Candidate,” “Anchors Away” and “Guys and Dolls.” He had new musical hits, such as “Come Fly with Me” in 1958, “Only the Lonely” in 1958 and “Nice 'n' Easy” in 1960.

His personal life became a disaster. After rumors in the tabloids of repeated affairs, he shocked the nation by abandoning wife Nancy and their three children, Nancy, Frank Jr., and Tina, marrying movie star Ava Gardner, then Mia Farrow. In corrupt pre-Castro Cuba, Sinatra was spotted in Havana with mobster Lucky Luciano, then was involved in a violent incident with journalist Lee Mortimer, who had written scathing articles on his alleged crime connections. Mortimer sued and according to biographer Kitty Kelley, received Mafia threats to drop the case or lose his life.

Whispers

Increasingly, Sinatra was tainted by whispers of Mafia ties. He became known for his seething anger and increasingly unhappy life. His children were embroiled in turmoil. Frank Jr. was allegedly kidnapped for ransom – but was accused of faking the incident for publicity. His oldest daughter, Nancy, got a big break with a hit “These Boots Are Made For Walkin’,” then with a poignant duet with her dad, “Something Stupid.”

At the age of seventy-one, in the broiling heat of summer in 1987, Sinatra’s voice had faded as had his crowds. He was no longer the skinny kid from Hoboken warbling to wholesome schoolgirls. Appearing to a small audience in Palermo, Italy’s Favorita Stadium, he declared that he was proud to be Sicilian. “Sinatra’s voice cracked a little as he spoke, and he looked more reflective than happy,” write biographers Anthony Summers and Robbyn Swan. “At another concert, in the northern Italian city of Genoa, he had a joke for his audience. ‘Two very important and wonderful people came from Genoa,’ he quipped. ‘One : Christopher Columbus. Two: my Mamma.’” The crowd cheered.

Praised by an Old Friend

He was honored at the Kennedy Center with the Presidential Medal of Freedom by his old friend Ronald Reagan, who had publicly embraced him – and for whom Democrat Sinatra enthusiastically campaigned.

Sinatra received the Congressional Gold Medal in 1997. He was the recipient of eleven Grammy Awards, including the Grammy Trustees Award, Grammy Legend Award and the Grammy Lifetime Achievement Award. After his death, American music critic Robert Christgau called him "the greatest singer of the 20th century.

To mark his 80th birthday, the Empire State Building glowed blue, his favorite color. A star-studded birthday tribute, “Sinatra: 80 Years My Way,” was held at the Shrine Auditorium in Los Angeles, featuring performers such as Ray Charles, Little Richard, Natalie Cole and Ella Fitzgerald singing his songs. At the end of the program Sinatra graced the stage for the last time to sing the final notes of the "Theme from New York, New York" with the group.