In Search of Dupree Bolton
How I tracked down the most mysterious musician in the history of West Coast jazz
Sometimes a music researcher needs to play the role of private detective. That happened to me when I tried to solve the mystery of the great missing jazz trumpeter Dupree Bolton.
I only told that story once. But the article never appeared in print—and was only available online for a few months.
This account deserves to be more widely known. So I’m sharing it with you in an updated version, both for its inherent interest—it’s a fascinating tale—and for the historical record.
The Honest Broker is a reader-supported guide to music, books, media & culture. Both free and paid subscriptions are available. If you want to support my work, the best way is by taking out a paid subscription.
In Search of Dupree Bolton (Part 1 of 2)
By Ted Gioia
For many years, people have asked me to tell about my search for the mysterious trumpeter Dupree Bolton. It’s a painful tale to tell, and has hardly become less so, even though decades have now passed since the events related here.
Certainly I’ve been remiss in waiting this long before sharing my account of this tragic and talented artist. But I welcome the opportunity finally to set the facts straight about Bolton's life and times.
This trumpeter caused a sensation on the West Coast when he appeared—unknown and out of the blue—at the close of the 1950s. He made a small number of recordings marked by his blistering speed and unbridled creativity on the horn, and seemed destined to rise to the top.
But Bolton was a secretive man, and—unlike every other player on the scene—went out of his way to avoid publicity. It was almost as if he had something to hide.
And then he disappeared—leaving the scene as suddenly as he had arrived.
That was where matters still stood, when I picked up the thread at the close of the 1980s—a quarter of a century after his disappearance. I was in the midst of writing my history of West Coast jazz, and Dupree Bolton was the biggest question mark in the whole book.
Who was he, really? How had he emerged from nowhere, already playing at superstar level? But most pressing of all—how could a player this talented simply fall off the face of the earth?
Dupree Bolton has long been both a legend and an enigma. He emerged on the West Coast scene of the 1950s, destroying all comers at the hottest jam sessions. No one knew where he had come from and Bolton never volunteered much information. When Downbeat local editor John Tynan tried to interview him, the trumpeter offered a single fact: “When I was fourteen I ran away from home.”
That was the complete extent of Bolton’s only known interview.
Bolton’s future would be as puzzling as his past. For a brief interlude, fans could enjoy his fiery playing in person but, except for a few LA jazz insiders, not many saw what he could do in the heat of battle on the bandstand. Those who did, however, would never forget it.
For the most part, Bolton’s reputation rests on two records. And what tantalizing records they are.
In particular, Bolton’s 1959 collaboration with saxophonist Harold Land, released as The Fox —an album which brought the trumpeter to the attention of the jazz world at large—stands out as a milestone moment even in that crowded year of jazz classics. The Fox announced to the world that this young LA trumpeter could withstand comparison with the very best on his instrument.
The title song, in particular, a maddeningly difficult composition penned by pianist Elmo Hope, finds Bolton spewing out lightning fast improvisations with a rhythmic drive and mastery that sound just as intimidating today as back in 1959.
Bolton’s solo begins at the 1:35 mark.
Even before the release of The Fox, the word-of-mouth buzz surrounding Bolton had begun to grow.
On October 15, 1959, Downbeat published a page of captioned photographs taken at the session. The text read, in part:
West Coast musicians who have heard the tapes from a recent recording session produced by Dave Axelrod are flipping over trumpeter Dupree Bolton. . . .
In [picture number] 3 Land looks as if he honestly didn’t believe what is coming from Bolton’s horn. Gifted with exceptional technique and fierce power, Bolton is being compared to the late Clifford Brown for the brilliance of his lines. But he’s something of a mystery man: not even Land seems to know where he came from.
Land had heard this fire-breathing trumpeter at a local club, and immediately knew he was the perfect hornplayer for his forthcoming session. Bolton boasted a flawless technique, an expressive tone, and—perhaps most striking of all—a fierce intensity, an electric quality which, especially at fast tempos, was like the aural equivalent of a SWAT team blasting down your door.
It was just too powerful—resistance was futile.
As if this were not enough, Bolton was a crack reader; Hope’s complex charts for the date, which would give many trumpeters fits, were navigated by Bolton with ease. If any question remained about Bolton, it had nothing to do with his musical talent, it was simply a puzzled wonderment over where this full-fledged trumpet star had come from. How could such a musician simply emerge, already at a world-class level, with no known history or background, immediately capable of playing with the very best?
Land, who passed away in 2001, still practiced his craft in Southern California when I was researching my book on West Coast Jazz, published in 1992. He remembered the session vividly, but could shed no light on the trumpeter. When The Fox was reissued in 1969, Land had commented: “If things had worked out right for [Dupree] he could have been one of the most important trumpet players of our time. There was a certain grandeur he was able to capture. . . He had a unique, fresh quality—something different.”
But instead of developing into a leader of the jazz world, Bolton vanished. And, if you can trust the surviving accounts, he was still getting better when he suddenly left the scene.
In a 1963 review of a club appearance Bolton gave with Curtis Amy, shortly before his disappearing act, John Tynan wrote:
This reviewer recently replayed a HiFi jazz album, The Fox, recorded about three years ago, which features Bolton in his first known recording. His playing was impressive then; today it is out of sight. . . .
Since joining Amy, he’s been turning heads around all over town. On trumpet he’s a fireball equipped with fearsome chops and a seemingly bottomless barrel of ideas. His sound is big and honest and sometimes so raw it rips a listener’s head off. . .
Bolton is shouting ‘Hear me!’ every time he puts the horn to his lips. And one has no choice but to listen.
As it turned out, Tynan witnessed one of the last performances at which he—or anybody else—would get to hear this extraordinary musician in the flesh.
Then fans got one final album, entitled Katanga!, featuring Bolton alongside Curtis Amy. Here in his swan song, Bolton again validates Tynan’s lavish praise. His playing is spectacular, on an album that might otherwise be just another hard bop session. Indeed, this is the kind of performance out of which legends are made.
Check out Bolton’s commanding solo on the medium tempo “Amyable.” It starts at the 2:14 mark.
And then fasten your seat belts for the title track “Katanga.”
On this barn burner, Bolton takes command straight out the starting gate, and his solo begins just 22 seconds later.
It was at this juncture, seemingly at the start of an illustrious career, that Bolton disappeared completely from the Southern California jazz scene, his departure every bit as unexplained as his earlier arrival. He left behind a glittering reputation, a handful of recordings and many unanswered questions.
Leonard Feather, the ultimate expert on jazz biography (he single-handedly wrote the first Encyclopedia of Jazz), penned the liner notes to the reissue of The Fox, but even Feather’s many sources of information were of no avail when it came to Bolton. Feather mentions Tynan’s brief interview, and could only add about the trumpeter: “Nobody knows where he came from or where he is today.”
During the twenty years following, little additional information came to light. Jazz historian Robert Gordon, writing in his 1986 book Jazz West Coast, provided no more biographical details, but his appreciation of the trumpeter was undiminished by the mysteries surrounding the musicians. “A photo on the album sleeve shows Harold looking on almost incredulously as the trumpeter works out,” Gordon writes; “those listening to the album are likely to have the same reaction.”
The 1988 Grove Dictionary of Jazz, the most exhaustive reference on jazz biography of its day, stated in its brief entry: “His few recordings reveal Bolton to have been a brilliant and stylish player; a mysterious figure, his reputation has, if anything, been enhanced by his tormented private life and obsessive personal secrecy.”
When I sat down to write this article, the Wikipedia entry for Dupree Bolton was only one sentence long. That’s how little we knew.
I had so little to go on when I launched my investigation. But I made a huge step forward when I got my hands on some research by British jazz discographer Bob Weir.
Alas, Weir’s info merely added to the mystery.
He had learned that Bolton had, in fact, recorded under an assumed name in the 1940s for the Buddy Johnson band. Even more intriguing: Bolton was said to be featured on a privately circulated recording made in 1980 by a group of Oklahoma convicts.
Weir published these details in his mimeographed Dupree Bolton Discography, a pamphlet which came into my hands in 1987. But all they proved was that Bolton had been hiding something even back in the 1940s. And that he somehow survived—and performed—long after his last commercial recording date in 1963.
Beyond that one could only speculate.
Late in 1988 I got a startling bit of information—by pure chance. And it gave me some hope of solving this 25-year-old mystery. A close friend and bandmate, saxophonist Mark Lewis, told me about an exceptional trumpeter he had heard playing on the streets of San Francisco. This trumpeter was working around Chinatown, earning tips by performing unaccompanied versions of ballads and jazz standards for passing tourists.
My friend had joined the trumpeter in an impromptu street-corner duet and had been markedly impressed by the caliber of his playing. I paid scant attention to this anecdote until he added that the trumpeter’s first name was Dupree.
I pounced on this, and asked for more details. Mark said he thought the musician’s last name was Bolden, like the New Orleans trumpeter Buddy Bolden.
I was riveted by this revelation. The similarity in names couldn’t be a matter of chance. Dupree ‘Bolden” seemed likely to be the mysterious Dupree Bolton, who had eluded the jazz world for decades. And if my friend’s story was true, Bolton was not only alive but still actively playing.
San Francisco has long been a haven for street musicians and I could well believe that Dupree was playing there. The San Francisco authorities have long been more tolerant of sidewalk players than their counterparts in many other cities. This tacit acceptance by the police, combined with temperate weather, made the “City by the Bay” the U.S. capital for wandering minstrels and the like.
Around the same time I was searching for Bolton, I would occasionally hear the noted saxophonist Sonny Simmons playing on a San Francisco street corner. Simmons, a fervid player with a top notch jazz pedigree, was relegated to playing requests for pedestrians. (Yet a short while later he rose again to prominence, in a gratifying turnabout. Simmons’s 1994 Ancient Ritual was released by a major label to great acclaim.)
But Simmons’s story is not an isolated one, and many of the street players deserve a better fate than the indifference of tourists and the noise of passing traffic. Given the sorry state of San Francisco’s jazz clubs and the fickleness of jazz fans, I imagined a similarly outcast fate for Dupree Bolton.
Almost two months passed before I was able to meet the Chinatown trumpeter. The winter weather had sent many of the older street musicians indoors. Finally, in late January of 1989, I was able to set up an interview at an Oakland musical instrument repair shop where I was told he would be waiting for me.
This first meeting, so long anticipated, lasted only twenty minutes—hardly more time than John Tynan had managed to secure during his brief, and only, discussion with the trumpeter three decades before.
The trumpeter showed up shortly after I arrived. He was an older black man with a full head of gray hair and a face that seemed much younger than what I had expected. Although Dupree Bolton’s date of birth was unknown to me, his first recordings, according to Weir’s discography, had been made in 1944. Assuming he was around twenty years old at the time he recorded, I anticipated a man around 65 years old. The person in front of me seemed younger than that. (Only in our later meetings would I notice tell-tale signs that suggested a greater age than I had initially suspected. These were most notable when he walked: his limp and slow movements gave hints of advanced years not evident in his visage.)
My interlocutor admitted that he was, in fact, the mysterious Dupree Bolton. “There will be no mystery about me, though, once you’ve heard what I have to tell you.” Facing me across a cluttered desk in the small backroom of the shop, he began providing me with a thumbnail outline of his life story.
Bolton had been born in Oklahoma City on March 3, 1929. This made him only 59 years old. His first recordings in 1944 were made not by a young man, but by a fifteen year old who had just run away from home. Against his parent’s wishes he had left to become a traveling musician with the Jay McShann band.
(Jazz musicians are as notorious as Hollywood starlets for lying about their ages. Although I later learned to treat many of Dupree’s claims with skepticism, I felt he was not deceiving me in this regard. His alleged birthdate fits with the one previously known biographical fact—his leaving home at 14—as well as with information he would later give me.)
“They just made a movie of Charlie Parker’s life,” Bolton told me. “They could do the same with me.”
Like many Oklahoma families of that time, the Boltons were sent by the ravages of the Dust Bowl to the more fertile pastures of California. Dupree’s parents were, however, more fortunate than the Oklahoma farm-pickers depicted in Steinbeck’s The Grapes of Wrath. Bolton’s father worked in the defense industry which was then a growing part of the Southern California economy. His mother created a stable home environment, and the young children were encouraged to study music. Dupree’s father could play all of the string instruments—while still in Oklahoma, the elder Bolton had been an important early influence on the legendary jazz guitarist Charlie Christian. Later he worked as a studio violinist in Hollywood, and he wanted his son to study the violin.
Bolton told me how he became a musician:
I started playing the violin when I was about four or five, but I wanted to play the trumpet. Later the music instructor at school gave me an E flat alto horn.
I took that home and my daddy said, ‘Hey, you can’t play this! This is an after-time instrument.’ But in three or four days, I had learned the fingering on that instrument and could play it. So my daddy told me, ‘Okay, I’ll get a trumpet for you.’
He sent to Sears & Roebuck for one of those mail order trumpets for me. I think it cost $19.95. I remember watching for the mail truck every morning, waiting for it to arrive. Finally one morning the mailman arrived and had that big package.
I rushed out there and there it was. I had a trumpet.
His rapid development on the instrument showed that the boy possessed remarkable talent. By the time he was fourteen, Bolton had gained enough proficiency to begin playing professionally. The war had created a shortage of musicians, and even top bands were willing to hire underage players to fill the constant gaps in the ranks.
Dupree’s big break came with his opportunity to join the Jay McShann band in 1944. He had not yet turned 15 and already Bolton was already in heavy musical company. Charlie Parker had just left when Bolton joined, and McShann was one of the most forward-looking bandleaders in the country.
“I told my mother I wanted to go on the road with that band and she said ‘You’re not going anywhere with any band. You’re going to stay here and go to school.’ So I went downtown to Main Street in Los Angeles and bought myself a suitcase and took it over to the hotel where the McShann musicians were staying. Over the next few weeks I’d sneak out my clothes, a pair of pants at a time, a shirt at a time. When I was done, I ran off with the band.”
His mother’s worst fears proved to be well grounded. Almost immediately Bolton was initiated into the world of drugs. The older bandsmen sent 15 year old Dupree to a drugstore with a forged prescription. When he returned with drugs he was give a portion as his reward.
“That was the first time I used dope. It was a painkiller for babies. Each dose had one ounce of opium in it. The dope addicts would take it, fix it, burn it, boil it, and draw the dope out of it.”
Within a short period, Dupree was heavily involved in drugs. By the age of 16 he was shooting cocaine with Charlie Parker in Bolton’s New York apartment. “I was in awe of him. He was a giant musician and everyone looked up to him because he was really the man. I was no exception.”
Like many jazz musicians of his generation, Bolton had the misfortune to follow Parker’s lead in both music and in drugs. From painkillers for infants, Dupree had soon progressed to heroin.
At this juncture, Bolton called our interview short.
He had shared with me his life story until his sixteenth year, but refused to say more—at least for now. But he promised to meet me the following morning and continue his narrative.
“They just made a movie of [Charlie] Parker’s life,” Bolton concluded—referring to Clint Eastwood’s recently released film Bird. “They could do the same with me.”
The next morning Dupree stood me up….
Coming soon: The second (and final) installment of “My Search for Dupree Bolton.”