10
'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.
09
'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.
08
'That's Life'
07
'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.
06
'Come Fly With Me'
05
'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!
04
'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.
03
'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.
02
'Night and Day'
01
'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.