Ever since I was  enough to think for myself, my music tastes and overall thought processes was very much old-school. Some may even call me an old-soul. And to be perfectly, I will admit I am somewhat. But can you blame me, when the days of old-although filled with bleakness, racism, and real struggles- produced amazing artists and big bands and other creative types. One in particular, a born-in New Jerseyan, rocked the world with his powerful vocals. I’m talking about the one, the only, Francis Albert (Frank, for short) Sinatra. Almost everyone in the world knows who he is. He has won multiple musical awards for albums, records, and vocals.  As an actor, he also won multiple awards for his roles in motion-pictures. He was the reason I started getting into musicals and singing, because I wanted to move people and have “the world on a string.”  Sinatra could make masterworks of theatre composers of the period, like Jerome Kern, Irving Berlin, George Gershwin, Cole Porter, and Richard Rodgers, and reinvent it in a way that lead people to rediscover it and for the songs to become classics. Sinatra is known for his good lucks and heavenly voice, but like everyone else, he had a dark side. He was involved with the mob. However, how did this boy from New Jersey sky-rocket to becoming this world-wide sensation, transcending time even?!

Sinatra was born in Hoboken, New Jersey – a stone’s throw away from my own hometown, Harrison, NJ – on December 12, 1915. His parents, Italian immigrants, where interesting in their own right. His father, Savario Antonio Martino Sinatra was a Sicilian boxer, fireman, and bar/tavern owner. On the other hand, his mother, Natalia Della (Garaventa) – also known as Dolly– was from Northern Italy. She had a huge presence in local politics and her son’s life and career. As a kid in Hoboken, in the 1900s, he pushed to work hard to get a better life. However, after hearing Bing Crosby, Sinatra decided to drop out of school to pursue music his senior year of high school.

Sinatra started his career as a saloon singer, even carrying his own P.A. system around. He then become part of a band, The Hoboken Four. However, the group disbanded, and Sinatra was discovered by Harry James, a trumpeter, and then Sinatra was picked up by Tommy Dorsey. Dorsey inspired Sinatra to work on his breathing with Dorsey’s smooth trombone melodies. During this time, Sinatra realized he mastered both ballads and up-tempos, and he made/featured on his first huge body of work, with songs like “I’ll be seeing you,” and chart topper, “I’ll Never Smile again. ” With the Dorsey band, he also appeared on Las Vegas Nights (1941) and Ship Ahoy (1942).

In 1942 he began his solo career,  although difficult for big-band singers on their own, he instantly found fame, and became the king of the bobbysoxers, aka the young women and girls who were his fans. He became the most popular singer of the era among teenage music listeners. He also came to be known as “Frankieboy,” “The Sultan of Swoon,” and, most popularly, “The Voice. His press agent, George Evans, decided to sell him as a street punk and thug, saved by his first wife, Nancy Barbato Sinatra. Frank Sinatra also began solo-acting in the 40s.

In April 1943, he made his first credited appearance in a motion picture, singing “Night  and Day” in “Reveille with Beverly”. “Anchors Aweigh” was his big break. He starred in lead alongside Gene Kelly, one of the top actors of his time. Sinatra himself, was known as “One-Take Charlie” as he favored spontaneity and energy, over perfection, Sinatra was instinctive and best at playing parts that mirrored his own personality. He gave strong and memorable performances in such films as Guys and Dolls (1955), The Joker Is Wild (1957) and Some Came Running (1958). Guys and Dolls is one of my favorite musicals, and in middle school, we performed it and it was a blast. I played the part of the intimidating General Cartwright of the Mission – yeah, ’cause I’m scary. He played in various serious and non-serious movies and had quite a repertoire.

In the mid 1940s, reports of his friendships with organized-crime figures, and newspaper accounts exposed of Sinatra cavorting in Cuba with the likes of Lucky Luciano and Joe Fischetti, a prominent mob figure. There was also the widely reported incident and  lawsuit in which Sinatra punched gossip columnist Lee Mortimer, an action for which Sinatra received some vindication in later years when it was revealed that Mortimer had collaborated with the FBI to discredit Sinatra. Whatever the cause, Sinatra began a five-year period of professional decline and personal depression. To add to his pain, the new  Columbia Records president Mitch Miller cajoled Sinatra to record several banal novelty tunes that compromised his artistic credibility. In 1952 his Columbia recording contract came due and was not renewed, he was dropped by his talent agency, his network television show was canceled, and Sinatra was considered a has-been. Ironically, and despite Miller’s demands, several of Sinatra’s recordings from this period are now considered among his best, with shining examples such as “Mad About You,” “Nevertheless,” “Birth of the Blues,” and, especially, his 1951 recording of “I’m a Fool to Want You.”

In 1953 Sinatra’s musical style took a huge turn. He signed with Capitol Records which, in about 9 years time, issued a series of recordings widely regarded as his finest body of work. He is credited (probably not accurately) with inventing the “concept album”—an LP collection of songs built around a single theme or mood. However, he and Nelson Riddle was a match made-in-heaven. Almost all of the albums the Sinatra-Riddle team made for Capitol— “In the Wee Small Hours” (1955), “Songs for Swingin’ Lovers!” (1956), and “Only the Lonely” (1958)—are masterpieces. His voice had deepened and grown in power and no longer did he croon-whisper,  as in the Columbia days. He attacked swing numbers with abandon and displayed his jazz influences with an uncanny sense of syncopation and an innate knowledge of “blue notes,” which he incorporated into the melody line. Two of his most praised recordings—“I’ve Got You Under My Skin” (1956) and “One for My Baby” (1958), both arranged by Riddle—showcase his varied approach to moods and tempos.

During the late 1950s and early ’60s, Sinatra frequently appeared on stage and in films with his close-knit band of friends known variously as “The Clan,” “The Summit,” or, most popularly, “The Rat Pack.” Peripheral members included actors Peter Lawford, Joey Bishop, and Shirley MacLaine and honorary member John F. Kennedy, but the core group was always Sinatra, Sammy Davis, Jr., and Dean Martin. The trio performed a largely ad-libbed act of boozy humour. It was also about this time that Sinatra generated more controversy for his connections with organized crime. His interactions with notorious individuals such as Sam Giancana damaged his fan base and jeopardized his political friendships. In 1960, at the request of Joseph P. Kennedy, Sr., Sinatra acted as a liaison between Giancana and the Kennedy family during John F. Kennedy’s presidential campaign, in order to ensure their votes – but after Kennedy’s war on crime, both parties cut ties with Sinatra. Sinatra continued to associate with mob figures throughout the years, saying “If you sing in joints, you’re gonna know the guys that run them”

Sinatra founded Reprise Records in 1960 and was allowed to record there simultaneously with his Capitol contract, which expired in 1962. During the early 1960s, Sinatra recorded furiously, releasing at least 14 albums of new material during the years 1961–63. His two 1960s masterpieces, “September of My Years” (1965) and the partnership with Brazilian songwriter Antônio Carlos Jobim, “Francis Albert Sinatra and Antonio Carlos Jobim” (1967), are among Sinatra’s greatest. He also had chart success during the decade with the hit singles “Strangers in the Night” (1966), “That’s Life” (1967), and “My Way” (1969). “My Way” being wildly recognized as his song and covered by many Sinatra fans.

He did say he would retire in 1971, but was back creating music again, during a shift in music tastes. His voice has grown increasingly gritty and coarse, from years of cigarettes and alcohol. His best albums towards the end, were volume one of the three-disc Trilogy (1980), the ballad collection She Shot Me Down (1981), and L.A. Is My Lady (1984), which featured an all-star orchestra. Duets (1993) and Duets II (1994), which paired Sinatra with several contemporary popular singers, were his last recordings. Sinatra also virtually retired from films during his later years. He concentrated instead on live performance and gave hundreds of international concerts from the late 1970s, with his final public performance in 1995. Even with multiple health issues, he still was a great entertainer, until the bitter end.

Sinatra changed the world, with his controversies and his voice and everything about him challenged the views about musicians and their limits. He was a musical genius and genuine entertainer. The 1,400+ recordings he made during more than 50 years as a performer are regarded as the most important body of work in American popular vocal music. Sinatra helped redefined singing as a means of personal expression. Through his life and his art, he transcended the status of mere icon to become one of the most recognizable symbols of American culture. He made music from days past relevant again and put a twist on them so they stay that way. He died May 14, 1998, in California, USA, due to bladder cancer, and heart and kidney disease. But, Frank Sinatra will keep singing and swinging on a star, as a one amazing legend who went from singing as waiter to the one of the most popular vocalists of all time.

You can check out his discography and music here.

You can check his filmography here.

For more in-depth biographies, check here, here, or here.