In Hoboken, New Jersey, in the year 1915, two Italian immigrants welcomed a baby boy who would grow up to be one of the best-selling and most recognized artists of all time.
Frank Sinatra started out listening to big band singers like Bob Eberle, Bing Crosby, and Gene Austin. Armed with a ukulele, he began singing professionally in high school. His group, the Hoboken Four, won some contests and got airtime on radio and TV. Soon bandleader Harry James noticed the blue-eyed lead singer and hired him.
But Sinatra wasnât happy with the James band, and switched to the Tommy Dorsey Orchestra after a couple of years. Thatâs where he really started to make a name for himself. He performed and recorded with Dorsey from 1940-1942, at which point he was longing for a solo career. It took a legal battle (and possibly a Mafia-connected threat) to get out of his contract, but he did so and went on to unprecedented success in the recording studio, concert hall, and movies.
After a long and stellar career, Sinatra died in 1998. Thereâs no question that he was one of the most important musicians of the 20
th century, and his influence is far from over.
With many of his tracks burned into the cultural consciousness (do you really need me to point you toward his recordings of âMy Wayâ and âNew York, New Yorkâ?), I tried to find some songs that even a fan might not be so familiar with. Iâve purposely left out his late-career collaborations with pop stars, which is not to say they arenât important or worth listening to.
There are so many great Sinatra cuts to choose from, I might as well have closed my eyes and picked at random! But I think I found some nice ones. Enjoy these eight tracks by Frank Sinatra.
- Track: âWhy Shouldnât Iâ
Album: The Voice of Frank Sinatra
Label: Columbia
Year: 1946
Originally issued as a collection of 78s,
The Voice of Frank Sinatra is his debut. The youthful voice is silky and full of nonchalant longing, the perfect croonerâs paradox: Donât show too much nuanced emotion, but always sound like youâre dreaming of something beyond our daily drudgery.
âWhy Shouldnât Iâ is a lesser-known Cole Porter number which had enjoyed only a handful of recordings between 1935 and this 1946 track. The sweet orchestral sound comes at the hands of arranger/conductor Axel Stordahl, who had also been with Tommy Dorsey and left at Sinatraâs urging. Here Stordahl is leading a small group that, for at least one of the sessions, included the oboe played by Mitch Miller, a groundbreaking arranger in his own right.
httpv://www.youtube.com/watch?v=65M9IhqQCK4
- Track: âSundayâ
Album: Swing Easy!
Label: Columbia
Year: 1954
You can hear a striking change between âWhy Shouldnât Iâ and this track eight years on. Itâs not just the rich texture of Nelson Riddleâs orchestral arrangements (Riddle would remain one of Sinatraâs favorite collaborators, helping to define his sound). Itâs also Sinatraâs singing. His style is more forceful and confident now, and his voice has greater dimension.
The melody of the 1926 song âSundayâ is by Chester Conn, setting lyrics by Jule Styne. It had a resurgence in popularity in the mid-â50s thanks to this Sinatra recording and one the following year by Bing Crosby.
httpv://www.youtube.com/watch?v=kONKxEql_Hs
- Track: âPocketful of Miraclesâ
Album: Sinatraâs Sinatra
Label: Reprise
Year: 1963
In 1960, Sinatra left Columbia to start his own record label, Reprise (still in operation, now owned by Warner), through which he created many hit albums. One of those was
Sinatraâs Sinatra, beloved for tracks like âCall Me Irresponsible,â âAll the Way,â and âWitchcraft.â
Less well remembered is the charming âPocketful of Miracles,â a Sammy Cahn and Jimmy Van Heusen tune. This is an example of the numbers Sinatra sometimes did with a childrenâs chorus (the most famous being âHigh Hopesâ). One of Sinatraâs many gifts was knowing what musicians to surround himself with, and here heâs relying on the great Billy May for arrangements and conducting.
httpv://www.youtube.com/watch?v=LbbtAMzr3dc
- Track: âWives and Loversâ
Album: It Might As Well Be Swing
Label: Reprise
Year: 1964
While his albums of pop duets in the 1990s might have put Sinatra on the map for a new generation, he did some fantastically fruitful collaborations earlier in his career. On
It Might As Well Be Swing, he shares the limelight with master pianist/composer/bandleader Count Basie. You simply canât go wrong with this pair-up. In fact, this was their second project together; they made
Sinatra-Basie in 1962.
A young Quincy Jones provided the arrangements. The track list, as you might guess from the album title, comprises songs from non-jazz genres, including Broadway and pop. âWives and Loversâ is a pop tune by Burt Bacharach and Hal David that had won a Grammy for Jack Jones the previous year. Sinatra clearly felt he had something to add, that something being Count Basie and a whole lotta swing.
httpv://www.youtube.com/watch?v=owujpzDOqjo
- Track: âOh, You Crazy Moonâ
Album: Moonlight Sinatra
Label: Reprise
Year: 1966
First, I tip my hat to whoever came up with this album title. Besides being an excellent pun, the title refers to the theme: Every song has to do with the moon. So thereâs âMoonlight Serenade,â âMoonlight Becomes You,â âReaching for the Moonâ-- you get the idea. (Not âFly Me to the Moon,â however, which was included on the
Might As Well Be Swing Basie album above.)
Jimmy Van Heusen and Johnny Burke wrote âOh, You Crazy Moon,â and this sax-heavy arrangement is by Nelson Riddle.
httpv://www.youtube.com/watch?v=WvIt7IErIW4
- Track: âYellow Daysâ
Album: Francis A. and Edward K.
Label: Reprise
Year: 1968
What a fantastic album this is! Sinatra teamed up with Duke Ellington and His Orchestra for some truly magical music-making. Billy May did the arrangements.
âYellow Daysâ was originally written (and often recorded) as a Latin jazz standard, a bolero to be exact, by Ălvaro Carillo. Sinatra squares up the rhythm of the vocal part, setting up a great contrast with Ellingtonâs sultry accompaniment.
httpv://www.youtube.com/watch?v=Hh6Gz_hzg-U
- Track: âDrinking Water (Aqua de beber)â
Album: Sinatra-Jobim
Label: Reprise
Year: 1969
Speaking of Latin jazz, Sinatra had had a big hit with his 1967 collaboration,
Francis Albert Sinatra and Antonio Carlos Jobim (which included their hit version of âGirl from Ipanemaâ), and they tried to recapture that lightning with this second album. Although sales were poor, a trend that Sinatra had to suffer through for the coming decade, thereâs some nice stuff here.
Jobim co-wrote âDrinking Waterâ with Vinicius de Moraes and Norman Gimbel. Itâs interesting to hear Jobimâs bossa-nova scat against Sinatraâs crooning.
httpv://www.youtube.com/watch?v=thS3uO9pnPA
- Track: âThe Best of Everythingâ
Album: L.A. Is My Lady
Label: Qwest/Warner Bros.
Year: 1984
The 1980s saw the resurgence of Sinatraâs career, and he never let up until his passing. This, however, was to be his final solo studio album, although he did those famous duet records almost ten years later.
L.A. Is My Lady features Quincy Jones and His Orchestra, only the second time Sinatra worked with Jones.
âThe Best of Everythingâ was composed by John Kander and Fred Ebb (who also wrote âNew York, New Yorkâ); as far as I can tell, they wrote it specifically for this record. Sinatraâs voice is craggy from age, and the bright sound of the Jones orchestra is a big change from the deep-toned Ellington or sweet-toned Riddle arrangements of old. But that distinctive Sinatra delivery is the same â thereâs no one else it could be.
httpv://www.youtube.com/watch?v=gGLfpoUX7EY
Header image courtesy of Wikimedia Commons/William P. Gottlieb.