Frank Sinatra | photo via

As important as any vocalist of the twentieth century, Hoboken, NJ-native Frank Sinatra (born December 12, 1915) rose out of Tommy Dorsey’s immensely popular orchestra of the 1940s to become the most famous popular singer of the 1950s and beyond. As we celebrate his 100th birthday this weekend on Sleepy Hollow, we focus on some of our favorite Sinatra recordings, as well as songs associated with ‘Ol Blue Eyes recorded by others.

Though he never abandoned the swinging jazz-pop of his early work, Sinatra hit a creative and commercial peak in the mid-’50s while working with arranger Nelson Riddle, compiling an astonishing array of excellent albums that highlighted Sinatra’s velvet-smooth voice and his singular approach to phrasing and melody. 1954’s Songs for Young Lovers, 1955’s In the Wee Small Hours, and 1957’s Where Are You? (which featured arrangements by Gordon Jenkins) are just a few of Sinatra’s efforts whose influence is still felt today.

And though his career would begin to decline in the ’60s, Sinatra managed a handful of masterpieces in that decade that include 1965’s September of My Years, the 1967 collaborative album Francis Albert Sinatra & Antonio Carlos Jobim, and “Somethin’ Stupid,” the #1 single also released in ’67 sung alongside his daughter, Nancy. While his albums would retain an inconsistency throughout the ’70s, ’80s, and ’90s, Sinatra continued to record and perform until his death in 1998.

Below, Keith Kelleher and I dig into the classic Sinatra songs that have carried on his legacy for so many years.

Frank Sinatra – “One for My Baby (And One More for the Road)” (Frank Sinatra Sings for Only the Lonely; Capitol; 1958)

It’s hard to believe that releasing two albums in the same year could be looked at as a relative break, but such is the case when looking at Sinatra’s most fertile era of the mid-to-late ’50s. 1957 saw some five recordings from the Chairman of the Board that include the classics Where Are You? and A Swingin’ Affair. And like the latter, 1958’s …Only the Lonely once again featured Sinatra alongside Nelson Riddle (he had wanted Gordon Jenkins, but he was unavailable), whose stark arrangements directly recall the pair’s earliest work together dating back to 1954. It’s difficult to refrain from associating standout “One for My Baby (And One More for the Road)” with the fact that Sinatra had recently gotten divorced from actress Ava Gardner. Of course, Sinatra had exhibited this kind of unrelenting melancholy and emotion before, but it seems to be taken to another level on this recording, allowing for an affecting, cinematic quality that is unique even amongst his vast catalogue. 1958 would also see the release of the somewhat better-known Come Fly with Me, and though that album also stands as one of his best, Sinatra displays a level of artistry on ...Only the Lonely that places it a level above its peers, added to in form on 1960’s Nice ‘n’ Easy and 1965’s September of My Years.

Frank Sinatra – “I’ve Got A Crush On You” (Nice ‘n’ Easy; Capitol,1960)

The perfect antidote to the heavy, morose ballads of albums like …Only The Lonely and …Wee Hours…, most of the selections in this collection show Sinatra in a breezy, less serious mood. Still, the arrangements have weight: the strings sway, and the horns coo and cajole as Sinatra lightens up, just a bit, for the listener. Nelson Riddle holds back even more than on their previous efforts, while Sinatra, on this classic track, shows again how his range of emotion using space in the music and lyric (in this case, courtesy of George and Ira Gershwin) is timeless. As a result, it feels as though he is singing directly to every listener, allowing for an intimacy all-to-rare in popular music.

Wes Montgomery – “Polka Dots and Moonbeams” (The Incredible Jazz Guitar of Wes Montgomery; Riverside; 1960)

Tommy Dorsey and His Orchestra (feat. Frank Sinatra) – “Polka Dots and Moonbeams” (RCA Victor; 1940)

“Polka Dots and Moonbeams” was the first hit Tommy Dorsey and His Orchestra had that included Frank Sinatra behind the microphone. The 1940 recording reached #18 on the charts and includes a then twenty-four year old Sinatra singing the Jimmy Van Heusen/Johnny Burke ballad with an irresistible nonchalance atop the orchestra’s subtle, trumpet-led arrangement. And while many have since recorded the song, Wes Montgomery’s rendition for his seminal 1960 release, The Incredible Jazz Guitar of Wes Montgomery, stands as a quintessential addition not only to the song’s recorded history, but also to Montgomery’s own sizable discography. Joined by pianist Tommy Flanagan, bassist Percy Heath, and drummer Albert Heath, Montgomery set the template for the sound that would put him among the elite class of jazz guitar, a list that includes artists like Charlie Christian, Jim Hall, Grant Green, and more recently, Bill Frisell and John Scofield. Montgomery’s reading is as tender and cool as Sinatra’s original, but his instrument allows him to employ his trademark use of harmony, which adds a complexity and warmth only really available to one who plays on strings. Wes Montgomery would go on to record many great albums, along the way fundamentally changing how guitarists of all genres approach the instrument, but while he may have come close or even matched it, he was never better than this.

Clifford Brown & Max Roach – “I Get a Kick Out of You” (Brown and Roach, Inc.; EmArcy; 1954)

Frank Sinatra – “I Get a Kick Out of You” (Songs for Young Lovers; Capitol; 1954)

Frank Sinatra first recorded Cole Porter’s 1934 composition “I Get a Kick Out of You” on his 1954 release Songs for Young Lovers, another collaboration that shows the remarkable synergy between Sinatra and arranger Nelson Riddle, in this case with Sinatra crooning over a decidedly swinging jazz combo colored by a full string ensemble. It is classic Sinatra and a true pillar of his formidable body of work. However, for pure energy and yes, unmitigated swing, Sinatra’s version is left in the dust by this take featured on Clifford Brown & Max’s Roach’s EmArcy debut, Brown and Roach, Inc. Accompanied by Harold Land on tenor sax, Richie Powell on piano, and George Morrow on bass, the song is an exercise in master soloing by all members save Morrow, with Brown leading the recording with an impeccable effort that is only topped by Roach’s astounding takeover halfway through. Of course, Clifford Brown would only record for another two years before his tragic death in a car accident on the Pennsylvania Turnpike, but this, alongside his other work with Roach, drummer Art Blakey, and vocalist Sarah Vaughan (among others), would cement his place as one of the greatest trumpet players of all-time. As essential as Sinatra’s definitive rendition of “I Get a Kick Out of You” may be, listeners are urged to explore this as an exciting alternative.

Frank Sinatra & Antonio Carlos Jobim – “Quiet Night of Quiet Stars (Corcovado)” (Francis Albert Sinatra & Antonio Carlos Jobim; Reprise; 1967)

Francis Albert Sinatra & Antonio Carlos Jobim is unlike any album previously recorded by Frank Sinatra, a fact made evident by the use of Sinatra’s full first and middle names in the title. Its unique nature is not only because the arrangements (this time courtesy of Claus Ogerman) are in-line with Jobim’s bossa-nova roots, but that Jobim, Sinatra’s musical partner in the recordings, is himself a songwriter on seven of the album’s ten selections. Fortunately, this is not merely an attempt for Sinatra to cash in on the bossa-nova craze, but a seminal effort that advanced the form in a similar way that Joao Gilberto and Stan Getz did with their classic recording released three years earlier. As music critic Stephen Thomas Erlewine points out, “[Frank Sinatra & Antonio Carlos Jobim is] a subdued, quiet album that used the Latin rhythms as a foundation, not as a focal point,” and as a result retains a continuity with Sinatra’s finest work alongside arrangers Nelson Riddle and Gordon Jenkins. But unlike that work, this album stands alone in Sinatra’s discography: an extension of what he does best, but also a completely singular piece that stands out amongst all the rest.

Bob Dylan – “Full Moon and Empty Arms” (Shadows in the Night; Columbia; 2015)

Frank Sinatra – “Full Moon and Empty Arms” (Columbia; 1945)

Frank Sinatra released his version of Buddy Kay & Ted Mossman’s “Full Moon and Empty Arms” in 1945, a ballad whose elegant orchestral arrangement, led by a consistent set of weeping strings, plays perfectly alongside Sinatra’s warm croon. Bob Dylan’s decision to release Shadows in the Night, a collection of interpretations of songs made famous by Sinatra is certainly peculiar, but Dylan also began his career interpreting the songs of others, and, in fact, has built his career upon the idea of assuming many different identities: Nashville Skyline Dylan is not the same as Blood on the Tracks Dylan is not the same as Highway 61 Revisited Dylan is definitely not the same as Shadows in the Night Dylan, and so on. Of course, many will question a voice as divisive as Dylan’s attempting to sing work that is representative of one of the best pure vocalists of the last 100 years. But Dylan has not sounded this good, or been this consistent, in at least nine years (when he released Modern Times), singing quietly but confidently over an excellent studio outfit that features Charlie Sexton on guitar, Tony Garnier on bass, and Danny Herron, whose pedal steel work steals the show on a number of Shadows in the Night‘s selections, including “Full Moon and Empty Arms.” The intimacy of the recordings allows Dylan to put much of himself into these interpretations, and reminds listeners that even if his tonality is off-putting to some, his approach and phrasing make him a mighty singer in his own right, more than fifty years after his first studio release.