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Ol' Blue Eyes: How Frank Sinatra made it big as an immigrant from Jersey

By Charles Apple

Eighty-five years ago Saturday — July 13, 1939 — 23-year-old singer Frank Sinatra cut his first record: a solo with trumpeter and bandleader Harry James.

“From The Bottom of My Heart” — with another Sinatra vocal on “Melancholy Mood” on the 78 rpm record’s B-side — was not a huge hit. But it would be a start for the man who would become one of the world’s best-selling music artists.

A Poor Jersey Kid Makes Good

Born to Italian immigrants in Hoboken, New Jersey in 1915, Frank Sinatra developed an interest in big band jazz music at an early age.

He dropped out of high school and then a business school, worked as a delivery boy for a local newspaper and then as a riveter at a shipyard. He sang at local social events and for free on area radio programs until 1920, when he joined a local singing trio. The newly-renamed Hoboken Four competed on a national radio show and won first place: A six-month contract for a concert tour.

In June 1939, trumpeter and bandleader Harry James — at left in the photo above, holding sheet music — signed Sinatra to a $75-a-week contract to perform with his band. A month later, James, Sinatra and his orchestra recorded “From the Bottom of My Heart” and “Melancholy Mood” for release by Brunswick records.

The recording, which listed Sinatra as performing a “vocal chorus,” was released in 78 rpm format — 33.3 rpm LPs wouldn’t be introduced until 1948, and 45 rpm “singles” would debut the year after that.

It reportedly sold only 8,000 copies. Sinatra continued to record with James and his orchestra but felt like he wasn’t finding success as quickly as he wished.

One day in late 1939, famed bandleader Tommy Dorsey was traveling through the Midwest when he turned on the radio and happened to hear Sinatra singing on a Harry James recording.

Impressed, he offered Sinatra a $250-a-week contract - big money, at the time. James reluctantly allowed Sinatra out of his previous contract.

With the Tommy Dorsey band, Sinatra found the fame he had desperately pursued. His very first onstage performance with the Tommy Dorsey band on Jan. 26, 1940, opened with Sinatra singing one of what would become his signature songs, “Stardust.”

Over the next three years, his work with Dorsey’s band would turn Sinatra into a superstar. Their single recordings would hit the Top 10 21 times and four would become No. 1 hits.

Over time, Sinatra begged Dorsey to allow him to make solo records. Continued success lured Sinatra into setting out on his own. After a messy legal battle with Dorsey — whose contract had pledged him 43% of Sinatra’s lifetime earnings, including solo projects — Dorsey finally ripped up the deal in 1942 to allow Sinatra follow his dream ... which was to compete with Bing Crosby.

Sinatra’s fame grew even more quickly in the 1940s. Teen girls bought his records and attended his shows. Newspaper writers began calling the girls “Sinatratics.” He began making film appearances and, by 1944, was playing leading roles.

Sinatra's 20 Best-Selling Records

Tracking Sinatra’s recording chart history is a difficult task: He recorded 59 albums and 297 singles over the course of his 54-year solo career. And that’s not counting the dozens of recordings he made as part of the Harry James and Tommy Dorsey bands.

In addition, formats changed over the years for song recordings as well as establishing sales records and top-10 lists. Billboard alone has used disc jockey plays, jukebox sales, record sales to determine the weekly singles sales list, which it now calls the Hot 100.

This data from Chartmasters shows overall unit sales for Sinatra’s single recordings.

...And How He Stacks Up Against The All-Time Greats

Chartmasters also has ranked the all-time best-selling artists using a formula that includes sales of physical records, tapes and CDs, digital downloads and streams. These are measured as “EAS,” or “Equivalent Album Sales.

Sources: “The Encyclopedia of Pop, Rock and Soul” by Irwin Stambler, “The Billboard Book of Top 40 Hits” by Joel Whitburn, Chartmasters.org, Library of Congress, NPR’s “Morning Edition,” Sinatra.com, TheFrankSinatra.com