Great Encounters #21: The influence of Tommy Dorsey on Frank Sinatra

September 29th, 2005

Great Encounters

Book excerpts that chronicle famous encounters among twentieth-century cultural icons




The influence of Tommy Dorsey on Frank Sinatra



Excerpted from

Tommy Dorsey: Livin’ in a Great Big Way


by Peter Levinson



With young men being drafted in profusion and some even volunteering for military service, big bands found new venues to work: Army and Air Force bases and Naval stations. With the pre-war and war period having nothing but a favorable effect on the band business, by 1940, dance bands were still big business. Altogether, big bands of every stripe earned one hundred ten million dollars that year.

After undergoing an artistic slump, Duke Ellington was enjoying a resurgence as a result of his having recently hired arranger Billy Strayhorn, tenor saxophonist Ben Webster and bassist Jimmy Blanton. In early 1940 the Ellington band recorded such significant singles as “Solitude,” a new version of “Mood Indigo,” “Jack the Bear,” and “Concerto for Cootie” (which eventually became “Do Nothing Till You Hear From Me”), earning Ellington a new following.

The phenomenon of the year, however, was the new singer with the Dorsey band, Frank Sinatra. Toward the end of January he made his first appearance with the band in Milwaukee. Dorsey immediately recognized his importance.  Jo Stafford recalled her first impression of Sinatra: “As Frank came up to the mic I just thought, ‘Hmmm-kinda thin?’ But by the end of eight bars I was thinking, ‘This is the greatest sound I’ve ever heard.'” When asked if his personality was any different then, Stafford replied, “In those years he had ten dollars in his pocket, and in later years he had a thousand dollars. That’s the only difference.

John Huddleston noted, “He had something. He sure knew it. I could sense that he was going to do whatever he wanted. You couldn’t miss it. He had the confidence that it was going to happen.”

Zeke Zarchy recalled, “When I had seen him with Harry James at the Chicago Theatre, the audience wouldn’t let him off the stage. This scrawny kid had such appeal. I had never seen a vocalist with a band go over like that. He had a certain quality. Jack Leonard was a good singer, but a band singer. Alan DeWitt was a good singer, but a band singer. But for somebody to get up like that! I could sense that he knew that also.

Zarchy added, “People have asked me if Frank was different in those days… . My impression was that he was in awe of being where he was. He was in a strange atmosphere, and he didn’t know any of the guys. “When I say he was standoffish, it’s not because he felt that he was better than anybody else. He knew that he was going to be a star because he wanted to be a star. I had that feeling. And I didn’t blame him one bit and neither did anybody else because we saw what his appeal was.

“One of the tunes he sang in that first show in Milwaukee was ‘East of the Sun,’ which was a ballad. It was not up. He swung it at that tempo; we didn’t play it at a swing tempo. Later on, I suppose Tommy altered some of the tempos to fit his style of singing.”

Along with two Pied Piper selections, the first two of what would total some eighty-three Frank Sinatra tracks with Tommy Dorsey were recorded in Chicago on February 1, 1940. (An incredible total of twenty-three of them reached the top ten on the Billboard chart during a three year period.) The first two tunes were “The Sky Fell Down” and “Too Romantic,” both arranged by Axel Stordahl. It was not a particularly stirring recording debut. His approach to a ballad was still rather tentative. A year later, however, a “live” recording of the former reveals an emerging stylist with a warm, individual yet intimate sound, one of the results of an endless skein of one-nighters.  On his first one-nighter Sinatra noticed an empty seat on the bus next to fellow newcomer Buddy Rich. He sat down and chatted with him before a “pit stop.” When asked why the seat was open, he was later told, “because he’s a pain in the ass.” After a few days Rich told his seat mate, “I like the way you sing.” This soon led to the cocky pair becoming roommates.

Stanley Kay, Rich’s longtime personal manager said, “Buddy told me they had their first argument when Frank started cutting his toenails at two o’clock in the morning. The clicking of the scissors disturbed Buddy and woke him up. An argument started — and no more rooming together.”

Jo Stafford remembers that Sinatra formed a closeness with Lee Castle and then with tenor saxophonist Dominic “Don” Lodice (Dominici LoGuidice), who, like Sinatra, was of Sicilian descent, and who had a wonderful sense of humor. Lodice soon was featured on the Dorsey record of “So What.” (Not remotely related to the later Miles Davis composition.) He and Sinatra later roomed together. For a time, the musicians referred to Frank as “Lady Macbeth” because he was always showering and changing his clothes.

But the budding friendship between Rich and Sinatra was about to become a rivalry. Dorsey watched as an intense conflict developed between his two budding young stars. Apparently, Edythe Wright was a big instigator in the feud between them. She would say things to Rich like, “What an S.O.B. Frank thinks you are,” and vice-versa. Dorsey kept a firm lid on the growing friction between the two of them, but he beamed as the dancers reacted to the excitement they were creating.

Sinatra had the decided edge, however. First of all, he was a singer, and thus communicated directly to the audience. The yearning quality in his voice, so characteristic of his ballad delivery, created an indelible impression, especially with young women. Dorsey sensed that and early on instructed not only Sy Oliver but also Deane Kincaide, alto saxophonist/arranger Freddie Stulce, and particularly Axel Stordahl (Paul Weston had recently departed) to write arrangements that would showcase his slightly built band singer with the prominent curl that fell seductively down over his forehead.

Morris Diamond, who had become Bobby Burns’s assistant, recalled the time at the Paramount when Dorsey announced, “And here’s our vocalist, Frank Sinatra.” The bandleader, forever alert to infractions of what he deemed improper demeanor on the bandstand, stopped the band, which then started vamping. He bellowed loudly so that everyone on the stage could hear him, “Go back there and comb your God Damn hair!” “I was standing in the wings,” said Diamond, “when Frank came to me and asked me to get him a comb, which I did, and after combing his hair he went back on stage.”

Intent on imparting the musical knowledge he had gained in his more than twenty-one years as a professional musician, Dorsey started spending time with Sinatra. Although he recognized the disparity in their singing styles, he suggested to Sinatra that he listen carefully to what Bing Crosby was doing. “… All that matters to him is the words, and that is the only thing that ought to matter to you!” (This was something Harry James had noticed was already important to the young singer.)

As Zeke Zarchy noted earlier, Sinatra was not only an able ballad stylist, but equally adept at handling up tempo arrangements. By listening intently to the essential jazz singer, Billie Holliday, on excursions to 52nd Street, he learned how to bend a note and lag behind the beat, while exhibiting an impeccable sense of time. Although he had attended Hoboken’s A.J. Demarest High School a mere forty-seven days, he had developed a penchant for reading, which gave him a clearer understanding of the intrinsic meaning of both individual words and phrases that in time led to his becoming a storyteller extraordinaire. He had also learned a great deal in this regard from watching the cabaret singer, Mabel Mercer, perform on 52nd Street.

In speaking, Sinatra retained his distinctive North Jersey/New York patois, but in his singing he constantly worked on his diction in order to bring out the mood and flow of the songs Dorsey assigned him. This underlined the intensity and emotional honesty with which he interpreted lyrics. The intimacy of his singing made every woman listening to him fell he was singing to her and her alone. In time came additional confidence and years later a sense of elegance that blended with his soft approach to the classic bel canto singing style he had adopted.

He also learned that the microphone could become his friend, just as Crosby had, which Dorsey pointed out to him. Using it not only to project his voice, he saw that it could provide shading to his vocal presentation, but he used it with economy. He also noticed how Dorsey made use of the microphone to enhance his own sound, particularly on muted solos.

The most essential ingredient that working with Dorsey brought to his singing style, however, was the result of his studiously observing Dorsey effortlessly navigate long musical phrases on the trombone. As he wrote in Life magazine in 1965 (with the assistance of the magazine’s then entertainment editor, the late bestselling author, Tommy Thompson), “He would take a musical phrase and play it all the way through seemingly without breathing for eight, ten, maybe sixteen bars. How in the hell did he do it? I used to sit behind him on the bandstand and watch, trying to see him sneak a breath, but I never saw the bellows move in his back. His jacket didn’t even move. I used to edge my chair to the side a little and peek around to watch him… I discovered he had a ‘sneak’ pinhole in the corner of his mouth – not an actual pinhole, but a tiny place where he was breathing [this was something Pop Dorsey had taught him]. In the middle of the phrase, while the tone was still being carried through the trombone…[he’d] take a quick breath and play another four bars with that breath.

“Why couldn’t a singer do that, too?… It was my idea to make my voice work in the same way as a trombone or violin — not sounding like them, but ‘playing’ the voice like those instruments.”

Reportedly close to a year later, Dorsey finished playing a solo and said to Sinatra, in reference to his discovering his secret of breathing, “Well Buster, (a nickname for Sinatra) did you find it?” Dorsey also stressed how much he developed his breathing by swimming laps under water at swimming pools. Sinatra acknowledged that he spent considerable time emulating Dorsey’s example by working out at the indoor swimming pool at Stevens Institute in Hoboken. Looking back on this formative period, Richie Lisella succinctly observed, “After he joined the band, Frank phrased exactly like Tommy played. I could tell the difference in his singing in just a few weeks.”

Jo Stafford, however, takes a completely contrary view of how Sinatra’s phrasing originated. “I do think it’s nonsense,” she says. “Frank just happened to have a wide ribcage like I’ve got, which means you take in more air and you learn to use it judiciously with lyrics. Tom [Dorsey] had a good ribcage, too. He knew how to spend it stingily.”

In time, Dorsey would become more than Sinatra’s musical mentor — he became his hero and a father figure to him. (Sinatra’s father, Marty was thought to be an ineffectual father.) Sinatra asked Dorsey to be the godfather of his first child, Nancy Sandra. Dolly Sinatra, Frank’s doting mother, whose own personality was equally as powerful as Dorsey’s, took to him immediately, and Sinatra’s wife invited him to their apartment for Italian dinners.

Beyond his musical influence, working with Dorsey intensified personal traits that Sinatra had in common with his mentor. Among them were his impatience, his insistence on exerting a firm control over every situation; his demands to achieve and maintain perfection; his largesse in helping his friends and those under extreme distress; his habit of often treating longtime employees with disdain, while constantly testing both their efficiency and their loyalty; his enjoyment of playing the dedicated host; his spendthrift ways – which didn’t always carry over to the paychecks of his underlings; his natural charm (which could be followed by abrupt mood swings); his constant search to associate himself with upper class people while in the long run finding that he was more comfortable with his own peers; the vengeance aimed at his enemies; and a complete inability to apologize for his actions even when confronted by the fact that he was wrong. The “My Way” aspect of Frank Sinatra’s character absolutely emanated from Tommy Dorsey. Why, he even walked like Dorsey!

The similarities could reach the level of absurdity. More than a decade later, after Sinatra left the Dorsey band, Jess Rand, on a visit to Sinatra’s dressing room, discovered a tube of “Dentists Prescribed,” a hard to find English toothpaste. The only other time he had ever seen that particular brand of toothpaste was resting on a shelf above the sink in Dorsey’s office bathroom more than a decade earlier.

As Richard Sudhalter cogently observed, “The way it works is when the autodidactic looks around and sees a way of doing things, or a way of expressing himself that appeals to him, he makes it his own…. And I think that Sinatra as a working-class kid from Hoboken learned that way.”

Tommy Dorsey: Living in a Great Big Way

by Peter Levinson


From the book, Tommy Dorsey: Living in a Great Big Way by Peter Levinson. Copyright © 2005. Published and reprinted by arrangement with Da Capo Press, a member of the Perseus Books Group ( All rights reserved.

Share this:

Comment on this article:

Your email address will not be published. Required fields are marked *

A Letter From the Publisher

An appeal for contributions to support the ongoing publishing efforts of Jerry Jazz Musician

In This Issue

The Modern Jazz Quintet by Everett Spruill
A Collection of Jazz Poetry — Summer, 2023 Edition

A wide range of topics are found in this collection. Tributes are paid to Tony Bennett and Ahmad Jamal and to the abstract worlds of musicians like Ornette Coleman and Pharoah Sanders; the complex lives of Chet Baker and Nina Simone are considered; devotions to Ellington and Basie are revealed; and personal solace is found in the music of Tommy Flanagan and Quartet West. These are poems of peace, reflection, time, venue and humor – all with jazz at their core. (Featuring the art of Everett Spruill)

The Sunday Poem

photo by William Gottlieb/Library of Congress
“Fledging” by John L. Stanizzi


photo courtesy of Henry Threadgill
Interview with Brent Hayes Edwards, co-author (with Henry Threadgill) of Easily Slip Into Another World: A Life in Music...The author discusses his work co-written with Threadgill, the composer and multi-instrumentalist widely recognized as one of the most original and innovative voices in contemporary music, and the winner of the 2016 Pulitzer Prize for Music.


painting by Henry Denander
A collection of jazz haiku...This collection, featuring 22 poets, is an example of how much love, humor, sentimentality, reverence, joy and sorrow poets can fit into their haiku devoted to jazz.

In Memoriam

Fotograaf Onbekend / Anefo, CC0, via Wikimedia Commons
A thought or two about Tony Bennett


"BG Boogie’s musical tour of indictment season"...The podcaster “BG Boogie” has weaponized the most recent drama facing The Former Guy, creating a 30 minute playlist “with all the latest up-to-date-est musical indictments of political ineptitude.”


Chick Webb/photographer unknown
Interview with Stephanie Stein Crease, author of Rhythm Man: Chick Webb and the Beat That Changed America...The author talks about her book and Chick Webb, once at the center of America’s popular music, and among the most influential musicians in jazz history.


FOTO:FORTEPAN / Kölcsey Ferenc Dunakeszi Városi Könyvtár / Petanovics fényképek, CC BY-SA 3.0 , via Wikimedia Commons
.“Community Bookshelf, #1"...a twice-yearly space where writers who have been published on Jerry Jazz Musician can share news about their recently authored books. This edition includes information about books published within the last six months or so…

Short Fiction

photo vi Wallpaper Flare
Short Fiction Contest-winning story #63 — “Company” by Anastasia Jill...Twenty-year-old Priscilla Habel lives with her wannabe flapper mother who remains stuck in the jazz age 40 years later. Life is monotonous and sad until Cil meets Willie Flasterstain, a beatnik lesbian who offers an escape from her mother's ever-imposing shadow.


Trading Fours, with Douglas Cole, No. 16: “Little Waltz” and “Summertime”...Trading Fours with Douglas Cole is an occasional series of the writer’s poetic interpretations of jazz recordings and film. In this edition, he connects the recordings of Jessica Williams' "Little Waltz" and Gene Harris' "Summertime."


photo by Bob Hecht
This 28-song Spotify playlist, curated by Jerry Jazz Musician contributing writer Bob Hecht, features great tunes performed by the likes of Frank Sinatra, Tony Bennett, Sarah Vaughan, Charlie Parker, Sonny Rollins, Bill Evans, Lester Young, Stan Getz, and…well, you get the idea.


photo of Wolfman Jack via Wikimedia Commons
“Wolfman and The Righteous Brothers” – a poem by John Briscoe

Jazz History Quiz #167

GuardianH, CC BY-SA 4.0, via Wikimedia Commons
Before becoming one of television’s biggest stars, he was a competent ragtime and jazz piano player greatly influenced by Scott Joplin (pictured), and employed a band of New Orleans musicians similar to the Original Dixieland Jazz Band to play during his vaudeville revue. Who was he?

Short Fiction

photo via PIXNIO/CC0
“The Sound Barrier” – a short story by Bex Hansen

Short Fiction

back cover of Diana Krall's album "The Girl in the Other Room" [Verve]
“Improvised: A life in 7ths, 9ths and Suspended 4ths” – a short story by Vikki C.


photo by William Gottlieb/Library of Congress
Long regarded as jazz music’s most eminent baritone saxophonist, Gerry Mulligan was a central figure in “cool” jazz whose contributions to it also included his important work as a composer and arranger. Noted jazz scholar Alyn Shipton, author of The Gerry Mulligan 1950s Quartets, and Jerry Jazz Musician contributing writer Bob Hecht discuss Mulligan’s unique contributions to modern jazz.


photo by Giovanni Piesco
Giovanni Piesco’s photographs of Tristan Honsinger


Maurice Mickle considers jazz venues, in two poems

In Memoriam

David Becker, CC BY-SA 3.0 , via Wikimedia Commons
“Tony Bennett, In Memoriam” – a poem by Erren Kelly


IISG, CC BY-SA 2.0, via Wikimedia Commons
Ella Fitzgerald, in poems by Claire Andreani and Michael L. Newell

Book Excerpt

“Chick” Webb was one of the first virtuoso drummers in jazz and an innovative bandleader dubbed the “Savoy King,” who reigned at Harlem’s world-famous Savoy Ballroom. Stephanie Stein Crease is the first to fully tell Webb’s story in her biography, Rhythm Man: Chick Webb and the Beat that Changed America…The book’s entire introduction is excerpted here.


Hans Christian Hagedorn, professor for German and Comparative Literature at the University of Castilla-La Mancha in Ciudad Real (Spain) reveals the remarkable presence of Miguel de Cervantes’ classic Don Quixote in the history of jazz.

Short Fiction

Dmitry Rozhkov, CC BY-SA 3.0 , via Wikimedia Commons
“A Skull on the Moscow Leningrad Sleeper” – a short story by Robert Kibble...A story revolving around a jazz record which means so much to a couple that they risk being discovered while attempting to escape the Soviet Union

Book Excerpt

Book excerpt from Easily Slip Into Another World: A Life in Music, by Henry Threadgill and Brent Hayes Edwards

Short Fiction

photo via
“Streamline Moderne” – a short story by Amadea Tanner

Publisher’s Notes

“C’est Si Bon” – at trip's end, a D-Day experience, and an abundance of gratitude


photo by William Gottlieb/Library of Congress
A Charlie Parker Poetry Collection...Nine poets, nine poems on the leading figure in the development of bebop…

Contributing Writers

Click the image to view the writers, poets and artists whose work has been published on Jerry Jazz Musician, and find links to their work


Photo of Stanley Crouch by Michael Jackson
Interview with Glenn Mott, editor of Victory is Assured: The Uncollected Writings of Stanley Crouch (photo of Stanley Crouch by Michael Jackson)


photo of Sonny Rollins by Brian McMillen
Interview with Aidan Levy, author of Saxophone Colossus: The Life and Music of Sonny Rollins...The author discusses his book about the iconic tenor saxophonist who is one of the greatest jazz improvisers of all time – a lasting link to the golden age of jazz


Designed for Dancing: How Midcentury Records Taught America to Dance: “Outtakes” — Vol. 2...In this edition, the authors Janet Borgerson and Jonathan Schroeder share examples of Cha Cha Cha record album covers that didn't make the final cut in their book

Pressed for All Time

“Pressed For All Time,” Vol. 17 — producer Joel Dorn on Rahsaan Roland Kirk’s 1967 album, The Inflated Tear


© Veryl Oakland
John McLaughlin and Carlos Santana are featured in this edition of photographs and stories from Veryl Oakland’s book, Jazz in Available Light

Coming Soon

An interview with Judith Tick, author of Becoming Ella Fitzgerald: The Jazz Singer Who Transformed American Song; A new collection of jazz poetry; a new Jazz History Quiz; short fiction; poetry; photography; interviews; playlists; and lots more in the works...

Interview Archive

Eubie Blake
Click to view the complete 22 year archive of Jerry Jazz Musician interviews, including those recently published with Richard Carlin and Ken Bloom on Eubie Blake (pictured); Richard Brent Turner on jazz and Islam; Alyn Shipton on the art of jazz; Shawn Levy on the original queens of standup comedy; Travis Atria on the expatriate trumpeter Arthur Briggs; Kitt Shapiro on her life with her mother, Eartha Kitt; Will Friedwald on Nat King Cole; Wayne Enstice on the drummer Dottie Dodgion; the drummer Joe La Barbera on Bill Evans; Philip Clark on Dave Brubeck; Nicholas Buccola on James Baldwin and William F. Buckley; Ricky Riccardi on Louis Armstrong; Dan Morgenstern and Christian Sands on Erroll Garner; Maria Golia on Ornette Coleman.

Site Archive