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10 Best Frank Sinatra Songs

While it is difficult to narrow down the best Frank Sinatra songs for a man who had a long and acclaimed career, there are several staples from the American songbook. A founding member of the famed "Rat Pack," Sinatra performed for presidents, toured internationally and socialized with starlets and mobsters. A recipient of eleven Grammy Awards, Sinatra will always be true American musical legend. Below are the best Frank Sinatra songs as chosen by AOL Radio listeners.
'I've Got You Under My Skin'
This Sinatra favorite was penned by Cole Porter in 1936. Sinatra first performed the song on the radio in 1946, but didn't record it until 10 years later as part of the 1956 album 'Songs for Swingin' Lovers.' The swinging big-band style builds to successive crescendos on the back of an arrangement by Nelson Riddle, who said he was inspired by Bolero.
Frank Sinatra I've Got You Under My Skin
'Strangers in the Night'
'Strangers in the Night' is a popular song written by Ivo Robic, made famous in 1966 by Frank Sinatra. The song won Sinatra the Grammy Awards for Best Male Pop Vocal Performance and Record of the Year, despite Sinatra's distaste for the song. His improvised "doo-be-doo-be-doo" at the end of the song is one of the most memorable improvisations in music, mimicking the melody of the song.
Frank Sinatra Strangers In The Night
'That's Life'
Written by Dean Kay and Kelly Gordon for Frank Sinatra, 'That's Life' was released on Sinatra's 1966 album of the same name. The song was a hit for Sinatra in the post-Beatles rock landscape of 1966.
Frank Sinatra That's Life
'Fly Me to the Moon'
This Frank Sinatra song was not originally recorded by the musical legend. Penned by Bart Howard, it was first recorded in 1954 by Kaye Ballard as a catalog piece. The song was recorded by many others, including Nat King Cole, before Sinatra included it on his 1964 album 'It Might As Well Be Swing.' Sinatra's version is the most recognized, manly due to Quincy Jones arrangement; a 3/4 waltz-time changed to to 4/4 to give it a 'swing' feel.
Frank Sinatra Fly Me to the Moon
'Come Fly With Me'
This song -- composed by frequent flyer Jimmy Van Heusen -- was specifically written for Sinatra and was the title track of his 1958 album of the same name. 'Come Fly Wit Me' sets the tone for Sinatra's album about exotic adventures.
Frank Sinatra Come Fly With Me
'My Way'
'My Way' is identical in melody to a French song 'Comme d'habitude,' but completely different in lyrics. Sinatra's version was penned by Paul Anka and was included on Sintra's 1969 album of the same name. The song tells the story of a man nearing death, recounting his life and that he lived it without regrets. Fittingly, Sinatra released it at a time where he thought he would quit the music business. We're glad he didn't!
Frank Sinatra My Way
'The Way You Look Tonight'
This Frank Sinatra song was originally performed by Fred Astaire and was featured in the film 'Swing Time,' later winning the Academy Award for Best Original Song in 1936. Sinatra is one of many performers (Billie Holiday, Tony Bennett, Michael Bublé, among others) to cover the song, and his version has been included in many films.
Frank Sinatra The Way You Look Tonight
'Theme From New York New York'
The song was originally performed by Liza Minelli in Martin Scorsese's 1977 film 'New York, New York.' In 1980, it was recorded by Frank Sinatra, for his album 'Trilogy: Past Present Future.' His version has since become the quintessential New York tune.
Frank Sinatra New York New York
'Night and Day'
'Night and Day' was Cole Porter's greatest contribution to the American songbook and has been recorded by dozens of singers, including Sinatra. Sinatra recorded the song five separate times, first in 1942, and culminating with a 1977 disco version including Joe Beck.
Frank Sinatra Night and Day
'Summer Wind'
This song -- with music by Henry Mayer and lyrics by Johnny Mercer -- had its first chart hit under singer Wayne Newton, but is most famous for it's profoundly sad Sinatra version. The Frank Sinatra song originally appeared on his 'Strangers in the Night' album and is one of his most-played recordings in various contexts, including a mid-2000s television ad campaign for Mastercard and Major League Baseball.
Frank Sinatra Summer Wind

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