Sinatra was very open about his influences as a singer. It’s well-known that as a young man he idolised Bing Crosby, but he also spoke of the inspiration he drew from the singing style of Billie Holiday.
It is Billie Holiday who was, and still remains, the greatest single musical influence on me.
Holiday and Sinatra were of an age, born in the same year, though she’d have been in the year above him at school, not that she spent much time in school. The year of their birth was before the release of the first “Jass” record and the first vocal blues record, but by the time the two of them started singing professionally, in the 1930s, jazz had become the first pop craze, and radio had spread the blues far and wide. As they were growing up, recording technology had progressed from singing into a horn as part of a mechanical recording system to an electrified system with microphones and loudspeakers. As you step forwards with technology, however, you sometimes lose something. The loud, raucous music of the 1920s had to be tamed and smoothed somewhat so that the new apparatus could cope with it.
Bing Crosby learned to sing into a ribbon microphone, one that would break if you sang to loudly into it. So his singing style was adapted accordingly, and became known as crooning.
Sinatra first saw Billie Holiday in the late 1930s, and at some point she offered him advice on how to sing the blues:
‘I told him certain notes at the end he could bend. … Bending those notes — that’s all I helped Frankie with.’
Holiday didn’t have much of a range, but her phrasing was a major influence on Sinatra whose voice was a more powerful and versatile instrument. I’m not a fan of how Sinatra sang in the 40s (still constrained, I think, by early microphones and still considered a mere adjunct to the real business of swing jazz, the orchestra and its leader); and I didn’t like what he started to do as his voice started to fade in his 60s, which was to (obviously) limit his dynamic range and lean into the gravel in his voice and to flatten his notes just a little too far.
But in his Capitol years, as previously discussed, and into his 50s with Reprise, his singing was spectacular. Of course, Holiday didn’t live into her 50s, a tragedy that hit Sinatra hard, but he was able to take full advantage of advances in recording technology: specifically, the Neumann U47 condenser microphone:
A major contributor to Frank Sinatra’s signature vocal sound when he moved from Columbia to Capitol was the U47 valve capacitor microphone that Neumann had begun manufacturing in 1949.
This mic was less fragile than the RCA 44 ribbon microphones that had been used up till then, which allowed for more attack from both brass sections and vocalists, and offered a brighter high end.
Anyway, this is all by way of an introduction to a short playlist of Sinatra singing the blues in the blues style. Of course, much of the Great American Songbook he drew from was based in the blues, and even a lot of the Broadway songs he chose had been influenced by the blues, but Sinatra’s torch songs and dance/swing numbers didn’t always sound terribly bluesy. I’ve selected a few, however, where you can hear the flattened blue notes that are characteristic of the blues. Sinatra did this often enough that it didn’t seem contrived but was a natural part of his style.
That’s Life (1966)
For me, this is the last great Sinatra track, before all the “My Way” and “New York, New York” nonsense that came after. While those latter two songs became show stoppers, they don’t appeal to me as they are both too on the nose to ring true. His kind of town, as any fule kno, is Chicago. Written by Dean Kay and Kelly Gordon in the early 60s, “That’s Life” is perhaps the Sinatra record that most sounds like it might come from 1966. That’s mainly because the band includes members of The Wrecking Crew, including Michel Rubini on Hammond, Glen Campbell on guitar, Hal Blaine on drums, and … it’s only fucking Darlene Love and the Blossoms on backing vocals.
I Got Plenty of Nuttin’ (1957)
This Gershwin number from Sinatra’s best Capitol Album A Swingin’ Affair comes from the controversial 1935 opera Porgy and Bess, which was first performed with an all African American cast, but having been written by white people was seen as a horrible kind of cultural ventriloquism. The song comes from Act 2, and is sung by the title character of Porgy. Taken out of its context, and in Sinatra’s hands, it loses its power to offend, and is simply a pop song based on the blues. Perhaps the most offensive thing about it is the spelling of ‘Nuttin’’ I absolutely love the instrumental interlude in this, as the band plays through the entire melody and really parps on that brass.
Stars Fell on Alabama (1957)
This 1934 song was composed by Frank Perkins and Mitchell Parish. The title phrase comes from a book and refers to the Leonid meteor shower’s appearance in 1833. The song has been covered by both Billie Holiday and Bing Crosby as well as the likes of Ella Fitzgerald and Doris Day. It is certainly one of the songs that people mean when they refer to the Great American Songbook. Sinatra’s version (again, from A Swingin’ Affair) has bluesy overtones, with extended and slurred words, alternative readings of the line, “My heart beat (just) like a hammer” and (most mysteriously) substituted “fractured ‘Bama” for “fell on Alabama.” So the Leonid meteor shower is breaking Alabama, shattering and cracking it. These Sinatra improvisations were his gift to the song, and you should by now be starting to believe that A Swingin Affair is the album to buy.
One for My Baby (And One for the Road) (1958)
This is another one from a musical – The Sky’s the Limit, the film version of which starred Fred Astaire and Joan Leslie. The youthful Sinatra dreamed away in many an Astaire musical, and this song was written for Fred Astaire, whose performance of the song is inevitably accompanied by a dance number. The bartender character, Joe, appears in the sequence too. To watch this, complete with uptempo tap-dancing bit, and then listen to what Sinatra does with the song (as performed in another movie, Young at Heart, made in 1955 with Doris Day as the love interest) is to experience popular music whiplash. This song plays straight into Sinatra’s self-image as a depressed torch singer (on every other album, at least). The original studio recording is on Only The Lonely (with Sinatra made up as a Pierrot clown on the Commedia dell’arte themed cover!)
I Got it Bad and That Ain’t Good (1957)
This is a Duke Ellington number (lyrics by Paul Francis Webster) from 1941. You’ll find versions of it by Nina Simone, Billie Holiday, John Coltrane, and so on. It’s a proper vocal blues, and Sinatra tackles it with a fabulous vocal, which you’ll find on what I’m going to call his bluest album, A Swingin’ Affair. But of course.
Nice Work if You Can Get It (1962)
This Gershwin tune is from 1937, and was again performed by Fred Astaire (with tap) in a movie: A Damsel in Distress, which also featured Joan Fontaine, who couldn’t dance. The film lost money. Sinatra recorded it at least twice, once on A Swingin’ Affair, and then again on Sinatra/Basie, an Historic Musical First, an album on which he radically reimagined several of his classic numbers, in new arrangements that explode the songs and make them new again. The Basie version is almost punky with its staccato rhythms and unusual phrasing which all but obliterates the original melody.
I Wanna Be Around (1964)
Another recording with the Basie orchestra, from the album It Might as Well be Swing.
This was written by Johnny Mercer in 1959, after receiving a message and a sample lyric from an Ohio woman who had been inspired by Sinatra’s two failed marriages to come up with the line, “I wanna be around to pick up the pieces when somebody breaks your heart.” The song is from the perspective of a spurned first wife who watches her partner leave her for another, just as Frank had divorced Nancy to marry Ava Gardner, only to be dumped in his own turn.
I Can’t Stop Loving You (1964)
This is a country song, by Don Gibson, written in 1957 and recorded by Sinatra with the Basie Orchestra in 1964. Ray Charles was the first to blues it up, in 1962, and Sinatra followed his lead in ’64. By the end of the 60s, Elvis also started performing it live, and artists as diverse as Dolly Parton and Van Morrison have covered it. Sinatra’s version is performed with many blue notes, and he sings with such relish that you can’t help but feel it a shame that he only recorded three albums with Basie.
Learnin’ the Blues (1962)
Sinatra first recorded this as a successful single in 1955, but then again with Basie on their first collaboration. It was written by former beauty queen Vicki Silvers, and dropped into Sinatra’s lap when a singer hoping to get signed took his recording of the song to Sinatra’s publishing company. The Hefti arrangement on the Basie album has more polish than the original recording, which many critics prefer. But you can’t knock Basie and Sinatra together, and I like the call-and-response brass arrangement and the more laid-back tempo. Sinatra puts a little less into the vocal, stepping back to make it seem casual, but he also makes it bluesier, so it works better here.
Sentimental Journey (1961)
This song was Doris Day’s first hit record, in 1945. Its release coincided with the end of the second world war, and became the “Tie a Yellow Ribbon” hit of that summer. It has since been recorded in over 150 versions (including one by Ringo), and translated into French, German, and Japanese. Sinatra’s version is on his second-last release for Capitol, Come Swing with Me, with orchestra conducted by Billy May, though May only arranged three of the songs. This was Sinatra’s last swing record for the label that relaunched his career, and he was already recording for Reprise. Because of this, I’ve always felt this record had Contractural Obligation written all over it, with some of the arrangements feeling rushed, as if speeded up simply to get it done quicker. Sinatra was recording four songs a day for Capitol, and then four more for his upcoming Reprise release. Then again, it’s an experimental record, with a doubled brass section playing in stereo, and Sinatra is still pretty damn good, even when he’s phoning it in.
Blues in the Night (1958)
Another Arlen/Mercer track, this was written for a film of the same name, a film noir (!) musical that starred almost nobody I’ve heard of. One scene required a blues song to be sung in jail, and this is it. I always find it interesting when an immortal song features in a forgettable movie. I’m even given to understand that the version in the movie “murders” the song, which turned out to be strong enough to survive such treatment. Sinatra’s cover, on Only the Lonely, isn’t even considered one of the important ones, but, well, he sings the blues.
The Lonesome Road (1957)
Finally, it comes to this, another track from A Swingin’ Affair, which is the most venerable song in this playlist. Written in 1927 by Nathaniel Shilkret and Gene Austin, it first appeared in the mostly lost mostly silent film Show Boat in 1929, which Wikipedia insists was not based on the musical Show Boat but instead on the book upon which the musical was also based. Huh. Apparently, it was originally a silent film based on the book, but then panic set in when the musical was a hit, so they added 30 minutes of songs with some cast members. Which explains, maybe, the inclusion of this song instead of “Ol’ Man River”, which is certainly the most famous song from the musical. “The Lonesome Road” isn’t even from the musical, but I guess is a gospel-style song in a similar vein. Sinatra’s version is beautifully arranged, properly bluesy, and opens the second side of the album. Another classic from a forgotten film.