Frank Sinatra

A Biography of One of the Greatest Singers of the 20th Century

A picture of actor and singer Frank Sinatra.
Promotional studio portrait of American singer and actor Frank Sinatra, 1950s. (Photo by Hulton Archive/Getty Images)

Who Was Frank Sinatra?

Known for his smooth, heartfelt voice during the “crooner-swooner” era, Frank Sinatra started performing in 1935 as the singer of a four-piece band in Hoboken, New Jersey. Between 1940 and 1943 he recorded 23 top-ten singles and reached the top position of the male-singer polls in Billboard and Downbeat magazines.

Sinatra went on to become a successful movie star, winning the Oscar for Best Supporting Actor for From Here to Eternity (1953).

He was popular as a man’s man (dressed in elegant suits but known for his legendary temper and stubbornness), while singing romantic songs that made women swoon.

Ultimately, Sinatra sold over 250 million records worldwide, received 11 Grammy Awards, and starred in 60 motion pictures.

Dates: December 12, 1915 -- May 14, 1998

Also Known As: Francis Albert Sinatra, The Voice, Ol’ Blue Eyes, Chairman of the Board

Sinatra Growing Up

Born in Hoboken, New Jersey, on December 12, 1915, Francis Albert Sinatra was of Italian-Sicilian descent. Being a 13.5-pound baby, the doctor forcefully brought him into the world by forceps, causing major damage to one of Sinatra’s eardrums (this would later make him exempt from entering the army during WWII).

Thinking the baby was dead, the doctor set him aside. Sinatra’s grandmother scooped him up and held him under cold running tap water at the sink. The baby gasped, cried, and lived.

Frank Sinatra’s father, Anthony Martin Sinatra, was a Hoboken fireman, and his mother, Natalie Della “Dolly” Sinatra (neé Gavarante), was a midwife/abortionist and political activist for women’s rights.

While Sinatra’s father was quiet, Dolly overwhelmed her son with love as well as her quick temper.

She sang in the Italian bel canto style at family gatherings while her son sang along. Sinatra also sang tunes he heard on the radio; his idol was the crooner Bing Crosby.

During high school, Sinatra took his first girlfriend, Nancy Barbato, to see Bing Crosby performing live in New Jersey, an event that greatly inspired him. Nancy believed in her boyfriend’s dream to sing.

While Sinatra's parents wanted their only child to graduate from high school and go to college to become an engineer, their son dropped out of high school and tried his luck as a singer.

To his parents’ dismay, Sinatra worked various jobs (including plastering walls for Nancy’s father) during the day and sang at Democratic Party meetings of the Hoboken Sicilian-Cultural League, local nightclubs, and roadhouses at night.

Sinatra Wins Radio Contest

In 1935, 19-year-old Sinatra joined with three other local musicians, known as The Three Flashes, and auditioned to appear on Major Edward Bowes’ very popular radio program, The Amateur Hour.

Accepted, the four musicians, now called The Hoboken Four, appeared on the radio program on September 8, 1935, singing Mills Brothers’ song “Shine.” Their performance was so popular that 40,000 people called in their approval.

With such a high approval rating, Major Bowes added the Hoboken Four to one of his amateur groups that toured the nation giving live shows.

Performing at local theaters and for radio audiences coast to coast in late 1935, Sinatra upset the other band members by receiving the most attention. Homesick and rejected by the other band members, Sinatra left the band by spring 1936, returning home to live with his parents.

Back home in New Jersey, Sinatra sang at Irish political rallies, Elks Club meetings, and Italian weddings in Hoboken.

Desperate to break out of small-time gigs, Sinatra took the ferry into Manhattan and persuaded WNEW radio management to give him a try. They worked him into 18 spots per week. Sinatra hired a New York voice coach named John Quinlan for diction and voice lessons to help him lose his Jersey accent.

In 1938, Sinatra became a singing waiter and master of ceremonies at the Rustic Cabin, a roadhouse near Alpine, New Jersey, for $15 per week. Every night the show was broadcast on the WNEW Dance Parade radio show.

Women were becoming attracted to Sinatra for his way of communicating vulnerability on stage, not to mention his blue eyes that would focus on one girl then another. After Sinatra was arrested on a morals charge (a woman accused him of breach of promise) and the case was dismissed in court, Dolly told her son to marry Nancy, whom she thought would be good for him.

Sinatra married Nancy on February 4, 1939. While Nancy worked as a secretary, Sinatra continued to sing at the Rustic Cabin and also on the five-day-weekly radio show, Blue Moon, on WNEW.

Sinatra Cuts a Record

In June 1939, Harry James of the Harry James Orchestra heard Sinatra singing on the radio and went to listen to him at the Rustic Cabin. Sinatra signed a two-year contract with James at $75 per week. The band played at the Roseland Ballroom in Manhattan and toured the East.

In July 1939, Sinatra recorded “From the Bottom of My Heart,” which didn’t hit the charts, but the following month he recorded “All or Nothing at All,” which became a major hit.

The Tommy Dorsey Orchestra was soon upstaging the Harry James Orchestra and Sinatra learned that Tommy Dorsey wanted to sign him. At the beginning of 1940, per Sinatra’s request to leave, Harry James graciously tore up Sinatra’s contract. At the age of 24, Sinatra was singing with the top big band in the nation.

In June 1940, Sinatra was singing in Hollywood when his first child, Nancy Sinatra, was born in New Jersey.

By the end of the year he had recorded 40 more singles, was touring the nation, singing on radio shows, and had appeared in Las Vegas Nights (1941), a feature-length movie featuring the Tommy Dorsey Orchestra in which Sinatra sang, “I’ll Never Smile Again” (another major hit).

By May 1941, Billboard named Sinatra top male vocalist of the year.

Sinatra Goes Solo

In 1942, Sinatra requested to leave the Tommy Dorsey Orchestra to pursue a solo career; however, Dorsey was not as forgiving as Harry James had been. The contract stipulated that Dorsey would be given one third of Sinatra’s earnings as long as Sinatra was in the entertainment industry.

Sinatra hired lawyers who represented the American Federation of Radio Artists to get him out of the contract. The lawyers threatened Dorsey with the cancellation of his NBC broadcasts. Dorsey was persuaded to take $75,000 to let Sinatra go.

Embarking on his solo career, Sinatra was welcomed by the screams of 5,000 swooning “bobby-soxers” (teenage girls of that era) at New York’s Paramount Theater on December 30, 1942 (shattering Bing Crosby’s attendance record). Billed as “The Voice That Has Thrilled Millions,” his original two-week engagement was extended for eight additional weeks.

Nicknamed “The Voice” by his new PR agent, George B. Evans, Sinatra signed with Columbia Records in 1943.

Sinatra Signs Contract for Film Career

In 1944, Sinatra started his film career with RKO studios.

Wife Nancy gave birth to son Frank Jr. and the family moved to the West Coast. Sinatra appeared in Higher and Higher (1943) and Step Lively (1944). Louis B. Mayer bought his contract and Sinatra moved to MGM.

The following year, Sinatra co-starred in Anchors Aweigh (1945) with Gene Kelly. He also starred in a short film on racial and religious tolerance titled, The House I Live In (1945), which won him an Honorary Academy Award in 1946.

Also in 1946, Sinatra released his first studio album, The Voice of Frank Sinatra, and embarked on a cross-country tour. But in 1948 Sinatra’s popularity slumped due to rumors of an affair with Marilyn Maxwell, womanizing, a violent temper, and association with the mob (which would always haunt him and be denied). That same year, Sinatra’s daughter, Christina, was born.

Sinatra’s Career Slumps and Rebounds

On February 14, 1950, Nancy Sinatra announced that they were splitting due to her husband’s affair with actress Ava Gardner, resulting in more bad publicity.

On April 26, 1950, Sinatra hemorrhaged his vocal cords on stage at the Copacabana. After his voice healed, Sinatra sang at the London Palladium accompanied by Gardner, whom he married in 1951.

Things continued to go downhill for Sinatra when he was let go from MGM (due to adverse publicity), received some bad reviews on his latest records, and had his TV show cancelled. It seemed to many that Sinatra’s popularity had waned and that he was now a “has-been.”

Down and out, Sinatra kept busy by hosting a couple of weekly radio shows and becoming a performer at the Desert Inn in the small desert town of Las Vegas.

Sinatra’s marriage to Gardner was a passionate but stormy one and didn’t last long. With Sinatra’s career in a tailspin and Gardner’s career on the rise, the Sinatra-Gardner marriage ended when they separated in 1953 (the final divorce occurred in 1957). However, the two remained life-long friends.

Luckily for Sinatra, Gardner was able to help get him an audition for a major role in From Here to Eternity (1953), for which Sinatra not only got the part but also received the Oscar for Best Supporting Actor. The Oscar was a major career comeback for Sinatra.

After a five-year career slump, Sinatra suddenly found himself in demand again. He signed a contract with Capitol Records and recorded “Fly Me to the Moon,” a major hit. He accepted an NBC multi-million-dollar TV contract.

In 1957, Sinatra signed with Paramount Studios and starred in Joker Is Wild (1957) to critical acclaim and in 1958, Sinatra’s Come Fly With Me album reached number one on the Billboard album chart, remaining there for five weeks.

The Rat Pack

Once again popular, Sinatra didn’t turn his back on Las Vegas, which had welcomed him with open arms when everyone else had dejected him. By continuing to perform in Las Vegas, Sinatra brought in legions of tourists who came to see him and his movie-star friends (especially the Rat Pack) who would often come visit him on stage.

The main members of the Rat Pack of the 1960s consisted of Frank Sinatra, Dean Martin, Sammy Davis Jr., Joey Bishop, and Peter Lawford. The Rat Pack appeared (sometimes randomly together) on stage at the Sands Hotel in Las Vegas; their sole purpose was to sing, dance, and roast each other on stage, creating excitement for tourists.

Sinatra was nicknamed “Chairman of the Board” by his buddies. The Rat Pack starred in Ocean’s Eleven (1960), which was very popular with the public.

Sinatra starred in The Manchurian Candidate (1962), which was perhaps Sinatra's best movie, but was withheld from complete distribution due to President Kennedy's assassination.

In 1966, Sinatra recorded Strangers in the Night. The album became number one for 73 weeks, with the title song receiving four Grammys.

That same year Sinatra married a 21-year-old soap-opera actress named Mia Farrow; however, the marriage ended after 16 months. Sinatra had apparently asked his wife to co-star with him in a movie called The Detective, but when filming overlapped for another movie she was starring in, Rosemary’s Baby, which she remained committed to, Sinatra had her served with divorce papers.

In 1969, Sinatra recorded “My Way,” which became his signature song.

Retirement and Death

In 1971, Sinatra announced his (short-lived) retirement. By 1973 he was back in the studio recording his Ol’ Blue Eyes Is Back album. The following year he returned to Las Vegas and performed at Caesar’s Palace.

In 1976 he married Barbara Marx, his neighbor in Palm Springs who had been a Las Vegas showgirl married to Zeppo Marx; they remained married for the rest of Sinatra’s life. She toured with him worldwide and together they raised hundreds of millions of dollars for charities.

In 1994, Sinatra performed his final public concert and was awarded the Legend Award at the 1994 Grammy Awards. He made no further public appearances after suffering a heart attack in January 1997.

On May 14, 1998, Frank Sinatra died at the age of 82 in Los Angeles.