Even cheap mp3s on iTunes cost money, and it can be daunting to a financially challenged music fan to build a library of music that they’re really only curious about and not sure about just yet. In the Essential Download Series, we’ll take a look at groundbreaking and influential artists from each of music’s three classic ages and give you a place to start your own exploration of their music. In this installment, the second pop star, and the biggest by far, Frank Sinatra..


Bing Crosby was the first pop star of the modern era, but it was Frank Sinatra who pioneered the intimate style needed to sing to a microphone. It was that intimacy - the vulnerability of his recorded voice and not the high-volume singing needed in the concert hall - that ushered in the era of the pop star, and gave Sinatra a sixty-plus year career.


My Way (1969) The  lyric was written by Paul Anka, set to a French song "Comme d'habitude," Sinatra's version became his signature tune, and one that he felt unable to escape for the remainder of his career. All of that aside, this is an older Sinatra at the peak of his power.     


It Was A Very Good Year (1965) Written by Ervin Drake and originally recorded by the Kingston Trio, Sinatra's lush and poignant reading is an American pop classic.

Frank Sinatra - Young


Fly Me to the Moon (1964) Written by Bart Howard in 1954 and originally titled In Other Words, several artists had hits with the tune before Sinatra recorded it. His version with the Count Basie Orchestra as arranged by Quincy Jones, is the Gold Standard.


Summer Wind (1966) Sinatra reached Number 25 on the Billboard Hot 100 with his reading of the Heinz Meier song that was written in German and titled Der Sommerwind. Wayne Newton also had a hit with this song, but Sinatra's is by far the most well-known.


That's Life (1966) Sinatra heard soul singer O.C. Smith's version of the Dean Kay song and turned it into a Number 4 hit on the Billboard Hot 100 in 1966. Often parodied, and even more often covered, this version is nothing but a full-on exhibit of a singer in command of every facet of his instrument.


I've Got the World On A String (1953) Written in 1932 by Harold Arlen, this jump blues classic was one of Sinatra's first recordings with long-time band leader Nelson Riddle.


Tennessee Newsboy (Newsboy Blues) (1952) Most people equate Sinatra with lush orchestral pieces or Big Band Swing mixed with an occasional foray into Easy Listening pop, but this 1952 made-for-radio recording finds Sinatra in the midst of pedal steel and Country Swing.


Send In the Clowns (1973) Written by Stephen Sondheim for the musical A Little Night Music Sinatra is at his wounded and poignant best.


Luck Be A Lady (1966) From the 1950 musical Guys and Dolls no song captures the spirit of the Rat Pack and the entire Las Vegas 1960s culture like Sintra's version. 


Moonlight in Vermont (1950) Pretty much a romantic tourism ad for the Green Mountain State, the 1944 tune is also an extremely difficult song to sing because of the way it is written. This may come in handy at some obscure Trivia Night somewhere: Moonlight In Vermont is the rare pop tune with lyrics that don't rhyme, and it is also maybe the only American pop tune written with each verse as a haiku.