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Chronology: A Look Back at the Career of Frank D’Rone

If you’ve never heard of the singer and guitarist, you’re not alone—but you should do something about it

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Frank D'Rone (photo: Mark Sheldon)
Frank D’Rone at the 2012 Chicago Jazz Festival (photo: Mark Sheldon)

Frank D’Rone might be the finest jazz singer and balladeer most listeners have never heard of. At least outside of Chicago, where he was a connoisseur’s favorite and a regular on the nightclub and saloon scene for decades until his death in 2013 at 81. 

Here is a singer (and guitarist) inhabiting his own creative space between Nat King Cole and Frank Sinatra. D’Rone delivers the Great American Songbook with the individuality of a musician confident in what he wants to say and how he wants to say it. A premier storyteller, he’s jazzier than Sinatra and Tony Bennett, hipper than Mel Tormé, punchier than Cole. Lithe, effervescent, and as inviting as a smile, his debonair baritone connects the dots between music, words, and nuanced expression. 

D’Rone squares the circle of jazz singing: He approaches the melodic line with the spontaneity and rhythmic security of an improvising horn yet commits himself wholly to the integrity of a song’s words and meaning. Everything he does is guided by taste as infallible as Ted Williams’ eye at the plate. 

He cemented his greatness with four largely forgotten LPs recorded for Mercury between 1959-62. Fresh Sound reissued the first two, Frank D’Rone Sings (1959) and After the Ball (1960), on a single CD in 2019. The former places D’Rone with small and large Chicago ensembles arranged by Dick Marx or William Russo and an all-star West Coast quintet (Shank, Kessel, Rowles, Mitchell, Manne). The latter, a Sinatra-styled concept LP with zesty Billy May big-band charts plus strings for the ballads, includes a cover photo marketing the 28-year-old D’Rone as a swinging lover: arms outstretched, cigarette in hand, tie loosened around his neck. All that’s missing is the fedora.  


D’Rone swings effortlessly through a swift “It’s You or No One” with long, legato phrases, perfect intonation, precise diction, and subtle syncopation. His elegant countenance and the open sound of his short vowels (“this,” “kiss,” “one,” “forever”) wink at Cole; but there’s an attractive, slightly nasal quality that’s all D’Rone. After a 12-bar ensemble interlude, he reenters from a side door, improvising what first sounds like a four-bar tag but turns out to be a sly modulation up a half step from E-flat to E major.

Look out, now!

Intensity rises as D’Rone takes savvy liberties with notes and rhythms. To start the second half-chorus (“Please don’t say no to my plea”), he soars elatedly to a fourth above the written melody—a signature D’Rone move—and ping-pongs between two notes as if he were the lead trumpet in a Basie shout chorus. A thrilling finish leaves good bumps in its wake.


“Everything Happens to Me” on Frank D’Rone Sings epitomizes his heartrending ballad singing. His conversational phrasing has Sinatra roots, and he further channels Frank by reverting to rubato in the second bridge and singing “I’ve mortgaged all my castles in the air/I’ve telegraphed and phoned” in one gulp of air to carry over the bar line. Still, the alluring timbre of his voice is singular. So is the unique way he climbs the scale above the melody to express the desperation of the lyric.

No wonder Cole was so moved by hearing D’Rone at a Chicago watering hole in 1958 that he wrote the liner notes for Frank D’Rone Sings: “A singer with an individual sound that invites no comparisons.” No wonder that, according to the Chicago Tribune, Sinatra once told the owner of the hungry i in San Francisco, “Here’s a guy who phrases better than me!”

Born Frank Caldarone in Brockton, Mass., D’Rone grew up in Providence, R.I. He played guitar and sang on stage from age five, moving to New York after high school and later apprenticing with road bands, before landing in Chicago in 1957. A growing buzz piqued Mercury’s interest, but the company also believed D’Rone might cross over to teenagers, so he recorded singles for rock & rollers as early as 1957-58. The material is beneath D’Rone, and only the backbeat-driven “Strawberry Blonde” (1960) got minor traction, spending six weeks on the U.K. singles chart, peaking at No. 24. 


His third LP, Try a Little Tenderness (1960), aims for the commercial adult market. D’Rone nearly drowns in arranger Belford Hendricks’ sappy choir and strings but still transcends. His final Mercury date, In Person, taped at the hungry i in 1962, is gold. Accompanying himself on guitar and backed by unidentified piano, bass, and drums, he thrives in his natural habitat of cabaret intimacy and sophistication. The swingers sparkle with improvisation, the ballads mine method-actor depths. In a similar vein, don’t miss the YouTube clips of dynamic D’Rone performances on Playboy’s Penthouse, Hugh Hefner’s TV show from Chicago in 1959-61 with the flavor of a bachelor-pad party.  

He’s jazzier than Frank Sinatra and Tony Bennett, hipper than Mel Tormé, punchier than Nat King Cole.

Despite his gifts, D’Rone never broke the glass ceiling of being a singer’s singer. Like many others who straddled the jazz/pop fault line, he got buried by the British Invasion and the hegemony of rock in the ’60s. After his Mercury contract ended, he made a few youth-oriented singles for Columbia that went nowhere. A single LP for Cadet in 1968 was his last recording until the 1980s.


But D’Rone always worked. He traveled the supper-club, hotel, and nightclub circuits; played the Vegas lounges (hired at the request of friends like Sinatra); appeared on Johnny Carson’s, Merv Griffin’s, and Dean Martin’s TV shows; and in 1982 toured with Liza Minnelli. He leaned more into jazz in later years, often scat-singing in unison with his guitar. If you caught him live, count yourself privileged. If you didn’t, the records await. 

Further Listening

Brand New Morning (Cadet) 
D’Rone in strong voice in 1968, though I find the material uneven and the production and arrangements’ au-courant pop vibe a bit dated. 

This Is Love, This Is It (Sapphire)
Brilliant singing, fine guitar playing, a crackerjack Chicago quintet, A-list material. This rare 1984 LP demands reissue.


Double Exposure (Whaling City Sounds)
A striking valedictory issued in D’Rone’s 80th year, half with big band, half with just guitar. His voice has lowered and darkened, but his expressive musicianship never falters.

Mark Stryker

Mark Stryker is the author of Jazz from Detroit (University of Michigan Press), named Jazz Book of the Year in the 2019 JazzTimes Critics’ Poll. Inducted into the Michigan Journalism Hall of Fame in 2020, Stryker covered jazz, classical music, and visual arts for the Detroit Free Press from 1995 to 2016. He also grew up working as a jazz alto saxophonist.