An irresistible baritone voice and an effortlessly cool demeanor

Frank Sinatra

Frank Sinatra

It’s been 60 years since the peak of his career, and Frank Sinatra is still considered the King of Cool. As one of the best-selling musical artists of all time, Sinatra never compromised his artistic integrity. This devotion to personal style makes him a legend in the jazz community and beyond.

Sinatra was born in Hoboken, New Jersey in 1915. When he was growing up, he was known around town as a rabble rouser. He dropped out of high school in his early teens, and when he was 23, he was arrested for adultery and seduction. Though he worked odd jobs to support himself through his teens and early twenties, his true passion was music. Bing Crosby was an early influence, and Sinatra learned to sing by imitating Crosby and other jazz singers. In fact, he never received any formal training in music.

Nevertheless, he was persistent in his goal of pursuing music. He sang in his high school’s glee club, then after dropping out, began singing for tips at local nightclubs. In 1935, he joined The Three Flashes, a local band who changed their name to the Hoboken Four when Sinatra joined. They had quite a bit of success around town, but Sinatra left the band not long after. A few years later, he joined swing bandleader Harry James, and in 1939, he made his recording debut, titled "From the Bottom of My Heart."

That same year, Sinatra was asked by Tommy Dorsey to join his band, one of the most sought-after swing ensembles of the time. However, Sinatra was still under contract with James. But James saw potential in Sinatra and let him out of his contract early so he could join Dorsey. Afterward, Sinatra’s rise to fame was monumental. Over the course of two years, he and Dorsey released hit after hit and toured the country. Their song “I’ll Never Smile Again” stayed at the top of the pop charts for three months. In 1941, Sinatra won Down Beat and Billboard magazines’ polls for best male singer.

Sinatra left Dorsey’s band in 1942 after a personal dispute. By this point, he was a considered a teen idol and had the nicknames "The Voice" and "The Sultan of Swoon." His debut at the Paramount Theater that same year nearly caused a riot due to the sheer number of screaming fans.

Sinatra started his solo career by signing with Columbia in 1943. Seven of his first nine songs under the label became chart toppers. By the mid-’40s, he also started acting in Hollywood movies. In 1945, he first starred alongside Gene Kelly in Anchors Aweigh. Sinatra and Kelly would work on many movies together throughout the ‘40s. Yet by the late ‘40s, Sinatra’s popularity was slipping. His singles appeared lower and lower on the charts, and his movies did not sell as well. He took a break from public life in the early ‘50s, brought on by hemorrhaging his vocal cords on-stage at the Copacabana.

But the mid-’50s would signal a new stage in Sinatra’s career. In 1951, Sinatra played his first show in Las Vegas at the Desert Inn. Along with the rest of the Rat Pack, Sinatra’s name would become synonymous with Las Vegas. In 1953, he won an Academy Award for his performance in From Here to Eternity. That same year, he’d sign with Capitol Records, and under this label, Sinatra would become better known for a more mature, jazzier sound -- a far cry from his earlier pop hits. During this era, Sinatra would record many of his signature songs: “Come Fly With Me” (1957), “Angel Eyes” (1958), and “I’ve Got You Under My Skin” (1956).

Even with the rise of rock in the ‘60s, Sinatra still managed to stay on top. He found his own record label, Reprise, in 1960. His first album on his own label, 1961’s Ring-a-Ding-Ding! hit number 4 on the Billboard charts. In 1965, he starred in one of his most commercially successful films, Von Ryan's Express. That same year, he headlined the Newport Jazz Festival alongside the Count Basie Orchestra. In 1968, he recorded his ultimate signature tune, “My Way.”

The ‘60s were also the rise of the Rat Pack -- Dean Martin, Sammy Davis, Jr., Peter Lawford, and Joey Bishop -- Sinatra’s group of hard-partying friends who’d star in movies, collaborate on songs, and of course, party in Vegas together.

Sinatra’s career slowed down in the ‘70s. He announced his retirement during a June 13, 1971 performance, though only two years later he’d come out of retirement with the album Ol' Blue Eyes Is Back. And he’d continue to perform for more than 20 years. His last performance was on February 25, 1995, at the closing of the Frank Sinatra Desert Classic golf tournament. He died on May 14, 1998 at age 82.

Standards like “New York, New York” and “My Way” are still beloved for the smooth sound of Sinatra’s voice and the lush orchestration behind him. Though never much for bebop or other avant-garde jazz movements, Sinatra personifies the attitude behind swing and cool jazz, an attitude that would carry over to rock and roll singers and beyond. With an irresistible baritone voice and an effortlessly cool demeanor, Frank Sinatra set the scene for 20th-century American music.

Frank Sinatra Videos

002 A Man And His Music Part II

Frank Sinatra -- A Man and His Music: Part 2

It's clear that a lot time was put into the set for Frank Sinatra's 1965 TV special "A Man and His Music." A ton of space was required to accommo

01 Sinatra In Japan Live At The Budokan Hall Tokyo . 1985 .

Frank Sinatra at Tokyo's Budokan Hall

Frank Sinatra's fame wasn't limited to the U.S.

Frank Sinatra -  Caesars Palace 1978 -  Part 3

Frank Sinatra -- Live at Caesar's Palace: Part 3

Sinatra opens up this portion of his live performance with a short comedic bit.

Frank Sinatra Spectacular   SL 1965

A Frank Sinatra Spectacular

Anyone well-versed in jazz knows about "The Rat Pack," featuring Sinatra, Dean Martin, and the incredibly talented Sammy Davis, Jr.

Frank Sinatra -  Caesars Palace 1978 -  Part 4

Frank Sinatra -- Live at Caesar's Palace: Part 4

This piece of Sinatra's 1978 performance at Caesar's Palace begins with the singer interacting with the crowd and talking about whiskey, Joey Lew

Frank Sinatra is Surprised by Don Rickles on Johnny Carson's Show, Funniest Moment

Don Rickles surprises Frank Sinatra on the Tonight Show

Frank Sinatra must have thought this was just going to be another typical interview on the Tonight Show with Johnny Carson.

Frank Sinatra -  Caesars Palace 1978 -  Part 5

Frank Sinatra -- Live at Caesar's Palace: Part 5

Frank Sinatra shows off his knowledge of Vegas by recommending "drink here....but don't eat here," before taking a request from a friend for the

001 A Man And His Music

Frank Sinatra -- A Man and His Music: Part 1

Frank Sinatra is no stranger to TV appearances.

Frank Sinatra -  Caesars Palace 1978  - Part 6

Frank Sinatra -- Live at Caesar's Palace: Part 6

Frank Sinatra takes a moment to acknowledge his backing band before trailing off with "The End Is Near," a song he admits he "hates" after singin

003 A Man And His Music + Ella + Jobim

Frank Sinatra -- A Man and His Music: Part 3

Part three of "A Man and His Music" features two fellow jazz legends of the era, Antonio Carlos Jobim and the great Ella Fitzgerald.

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