Ol' Blue Eyes: The Musical Career of Frank Sinatra

Frank Sinatra is one of the most well-known figures of music from the mid-20th century. He is one of the best-selling musical artists of all time, with hundreds of millions of record sales worldwide. 

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The Birth of Ol’ Blue Eyes:

Born Frank Albert Sinatra to Italian immigrant Parents, Natalina “Dolly” Garaventa and Antonio Martino “Marty” Sinatra, on December 12, 1915, in a tenement (a building of rented apartments, generally known in the late 19th to 20th century to be overly crowded and poorly maintained) in Hoboken, New Jersey. He was an astounding 13.5 pounds at birth and was delivered with the use of forceps, causing irreparable scarring to his left cheek, neck, and ear. Due to this, Sinatra sustained damage to his left eardrum throughout his entire life, and his baptism was delayed to April 2, 1916, at Saint Francis Church. Later in his childhood, Sinatra endured a mastoid operation (to remove infected tissue from the bone behind the ear), which caused additional scarring to his neck. During his teenage years, Sinatra suffered from cystic acne, which further added to his extensive scarring. His scarring initially caused him to be sensitive about his left profile, and he disliked being photographed from that angle. He often wore makeup to cover them, especially during his early career. However, as time went on, Sinatra embraced his scars. He went on to express, “Don’t hide your scars, they make you who you are.”

Amateur Hour:

Sinatra had an interest in music from an early age, often singing at his parents’ tavern for spare change, but it wasn’t until he was a teenager that he started to sing professionally. Rather than learning to read music, Sinatra learned to sing by ear, further highlighting his musical talent. His first real break in music was joining up with the 3 Flashes to create the Hoboken Four. This group went on to audition for the radio show Major Bowes Amateur Hour. They went on to earn a place on the show, earning $12.50 each. The group earned the show’s first-place reward with 40000 votes, earning a six-month contract to perform across the country on radio and stage. During their stint with Edward Bowes, Frank Sinatra became the lead singer of the Hoboken Four, attracting most of the attention of the girls watching their performances. This led to jealousy from the other members of the group, causing them to abuse Sinatra frequently. 

After their contract was over, the group disbanded, and Sinatra worked as a singing waiter at “The Rustic Cabin,” a roadhouse in Englewood Cliffs, New Jersey, which had a connection to a radio station in New York City. While he worked there, Sinatra began to sing with a group that performed with that radio station. While the pay wasn’t great, he knew this was how he was going to make it big. 

Harry James and Tommy Dorsey:

In March of 1939, Sinatra’s first solo studio recording was arranged by Frank Mane, who knew him from the Jersey City radio station WAAT, to record the song “Our Love.” This led Sinatra to be signed on a two-year contract with bandleader Harry James, during which he would release his very first commercial record, entitled “From the Bottom of My Heart.” However, no record he would release with the Harry James band would do well. Frustrated with his lack of impressive record sales with the Harry James band, Sinatra decided to leave the band and instead sign with Tommy Dorsey. 

Sinatra made his first appearance with the Tommy Dorsey band in January of 1940, during a show at the Coronado Theatre in Rockford, Illinois. During this performance, Dorsey recalled that he “would almost forget to take his own solos” (Lahr 59-60).

Tommy Dorsey would go on to become a large influence on Sinatra, who would copy his mannerisms, down to adopting his hobbies. He would also become the godfather of Sinatra’s first child, Nancy. 

With Tommy Dorsey, Sinatra would record more than 40 songs in the first year, including his first Billboard Top Ten hit. His popularity was burgeoning, and he wanted to go solo. 

“I Hope He Falls On His A**”:

He recorded four songs solo at a Bluebird recording session. These songs were “Night and Day,” “The Night We Called it a Day,” “The Song is You,” and “Lamplighter’s Serenade.” After hearing his solo recordings, Sinatra was convinced he had to become a solo artist, partially because he wanted to compete with Bing Crosby, a fellow singer. However, this led to a legal battle with Tommy Dorsey due to their contract, which had granted Dorsey almost half of Sinatra’s lifetime earnings. This was eventually settled in 1942, with Dorsey giving his farewell in a rather uncouth manner, saying “I hope he falls on his a**” (Lahr 60). Sinatra and Dorsey never made up.

Sinatra convinced the arranger of his solo recordings, Axel Stordahl, to come with him and be his personal arranger, and in June of 1943, he signed with Columbia Records as a solo artist. In that same year, he recorded nine songs, seven of which landed on the best-selling list. He also played his first solo appearance at a nightclub called Riobamba, as well as a concert in the wedgewood room of Waldorf-Astoria, which landed him a spot in New York’s high society. Less than a year into his solo career, Sinatra was more popular than Bing Crosby, as expressed by a Downbeat poll. 

In the later months of the second world war, Sinatra worked with the USO to go on trips and entertain troops in foreign countries alongside comedian Phil Silvers. These performances were also broadcast through the Armed Forces Radio Service (AFRS).

In 1946, Sinatra released his first solo album, entitled The Voice of Frank Sinatra. This album shot up to number one on the United States Billboard Top 100. Sinatra released his second album the following year, called Songs By Sinatra, which peaked at number two on the United States Billboard charts. That year, he also recorded his rendition of “Sweet Lorraine” with a group of jazz musicians known as the Metronome All-Stars, which included trumpeter Charlie Shavers and jazz legend Nat King Cole on piano. 

The Career Slump:

Sinatra released his third album, Christmas Songs By Sinatra, was released in 1948, and re-released in 1950 as a 10-inch disk, featuring such classics as, “Silent Night,” “White Christmas,” and “Have Yourself a Merry Little Christmas.” Unfortunately, this album only peaked at number 71 on the United States Billboard charts. This was the start of Sinatra’s career slump.

He had dropped to fourth on Downbeat’s top male vocalists, and next year, had dropped out of the top completely. He released his last two albums with Columbia in 1950, these being Dedicated to You and Sing and Dance with Frank Sinatra. After financial issues due to the divorce of his first wife, Nancy, he moved to Las Vegas after being rejected from Hollywood. His decrease in popularity was extraordinarily evident in his concert appearances, with him only filling up 150 seats in a venue rated for 1200 people. Despite low popularity and an unsteady relationship with his label, Sinatra recorded quite a few memorable songs during this period, including “If I Could Write a Book.” His last recording with Columbia before being dropped was “Why Try to Change Me Now,” in 1952.

“I’m Back, Baby, I’m Back!”:

In mid-1953, Sinatra played in a film entitled From Here to Eternity, which sparked a massive career revival. Sinatra recorded and filmed and performed in an incredibly densely packed schedule, giving himself his spark back. A few months before, he had met with Capitol records vice president Alan Livingston to sign a seven-year contract and get himself back into the music scene. His first recording with Capitol had been set to be in April, and Sinatra was to work with Nelson Riddle, arranger and musical director for Nat King Cole. After recording his first song with Riddle, Sinatra was ecstatic. He even went so far as to exclaim, “I’m back, baby, I’m back!” (Summers, Swan 191), and after a few more sessions with Riddle, he had prepared his first album for Capitol, which had released January fourth, 1954, and was entitled Songs for Young Lovers, which featured one of my personal favourite Sinatra songs, “My Funny Valentine.”  

Song of the Year, Album of the Year, and Top Male Vocalist:

In the same month of the same year, Sinatra had released the single “Young at Heart,” which was a roaring success, having peaked at number two on the United states billboard charts and winning song of the year. 

Sinatra released his second album with Riddle and Capitol in August of 1954, called Swing Easy, a jazz inspired album that was declared Album of the Year by Billboard. Sinatra had risen back to his glory as Top Male Vocalist not only for Downbeat this time, but also for Billboard and Metronome. 

The next year, Sinatra released his very first 12-inch Long Playing record, entitled In the Wee Small Hours. This album was one of the very first concept albums, meaning the tracks together held a meaning, rather than each track having its own theme. This album’s concept was that of melancholy and lost love, featuring songs such as “When Your Lover Has Gone” and “Can’t We Be Friends?”

In 1957, Sinatra released his first album with Nelson Riddle, and his first album in stereo. It was called Where Are You?, although it was later reissued as The Night We Called it a Day. 

The next year, Sinatra would release an album that would further revolutionise his career. The concept album Come Fly With Me was released on January sixth, 1958, and reached number one on the Billboard charts in its second week, and stayed there for five weeks. It was nominated for the Grammy Album of the Year award, although it didn’t win. The album was another concept album, this one was a musical tour of the globe, featuring songs like “Around the World,” “Brazil,” and “I Love Paris.” 

Reprise:

Sinatra had a good six years with Capitol Records, but he had grown discontent with the group. He wanted to own his own label. This was done at first with an attempt at acquiring a near-flatlining jazz label, called Verve Records, but Sinatra failed at making an acceptable offer. This caused Sinatra to have the idea to form his own label. One he would call Reprise. The label was founded in 1960, and Sinatra promised artists full creative control and the complete ownership of their work, which included publishing rights. He released his first album with Reprise in 1961, called Ring-A-Ding-Ding!, which was a large success, peaking at number four on the United States Billboard charts. The following year, Sinatra released an album entitled Sinatra and Strings, perhaps the most critically acclaimed album of Sinatra’s time with Reprise. The album reached number eight on the United States Billboard charts. This album also ushered in a new era of pop music, featuring big, lush orchestras.

In 1963, Sinatra had a long-awaited reunion with the man who he claimed was “the greatest arranger in the world” (Summers, Swan 192), Nelson Riddle, to record an album called, The Concert Sinatra. The album featured an impressive 73-piece orchestra that was conducted by Riddle. The album is considered by Sinatra biographer Charles L. Granata to be one of the best ballad albums recorded by Sinatra and Riddle. 

It didn’t stop there, though. Sinatra was on a roll. The next year, his song “My Kind of Town” was nominated for the Academy Award’s Best Original Song. And the next, he released the album September of My Years, which won the award for Grammy’s Best Album of the Year. The album was a throwback to Sinatra’s early concept albums for Capitol. A single from the album, and another one of my favourite Sinatra songs, “It Was a Very Good Year,” went on to win the Grammy Award for Best Male Vocal Performance. He won Grammy’s Album of the Year again the next year, with A Man and His Music, a double album that was a retrospective view on his musical career up to that point. 

Sinatra’s next album, That’s Life, was released in 1966, and both the album and the lead single of the same name landed on the United States Billboard charts’ top ten. Another single from the album was Sinatra’s first number one hit on the UK charts. 

Towards the end of his years with Reprise, in late 1968, Sinatra recorded his most popular song on the label, “My Way,” written by Paul Anka with Sinatra in mind. The song was released in 1969 and went to number 27 on the United States Billboard charts, but number five on the UK charts, it stayed in the UK charts for a record at the time, with 122 weeks. Despite its rocky start, the song became one of the most popular songs to be requested at funerals, as reported by NPR.

“Retirement”:

In November of 1970, Sinatra recorded the last few songs with Reprise before his retirement, which he announced later in June of 1971. This didn’t last long, however, as he came out of retirement less than three years later to record his album with Gordon Jenkins, called Ol’ Blue Eyes is Back, which was a decent success. The album peaked at number 13 on the United States Billboard charts and number 12 on the UK charts. 

Starting in the early 80s, Sinatra’s voice started to wane, and by the early 90s, he was starting to forget lyrics to songs during performances.

Frank Sinatra died peacefully in his sleep on May 14, 1998, at the age of 82. His funeral was held in Beverly Hills, California, at the Church of the Good Shepherd.

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My name is Brody Beck. I’m a sophomore here at Poudre. This is my first year with the Poudre Press. I’m a huge music nerd, and I adore attending local shows. When I graduate, I would like to go on to higher education to become an audio engineer at a recording studio and perhaps pursue my own interests in creating music.