The Four Comebacks of Art Pepper

Few jazz artists burned so brightly or paid such a high price on their path to greatness

You could read saxophonist Art Pepper at middle age like a painting—if you dared.

On his upper right arm, you saw a tattoo of a skeleton’s death head smoking an opium pipe—a harbinger both of the artist’s early death and its roots in self-destructive addiction. Below that, Pepper’s lower arm showcased the tragic and comic masks of ancient drama, representing the performer’s vocation and its often conflicting demands.

He put a naked woman near his heart, a sentimental gesture (Art never lost his tender, romantic side). There was another lady on his back, maybe there’s a symbol there too. But on his left arm, Art gave prime placement to Pan, the god of wild ecstasy, linked by tradition both to music and dangerous revelry. Finally, defusing the somber mood, Pepper added, higher up on the same arm, Linus and Snoopy from the Peanuts comic strip.

“I’ve always liked Peanuts,” he explained.

Pepper deeply regretted that release from prison prevented him from getting a planned Dracula tattoo. “It was going to be on my right arm over my vein,” he described. “The mouth would be open over the vein, and then when I fixed I could say, ‘Hey, wait a minute! I gotta feed mah man!’” This arguably would give him priority in a group setting, allowing Art to fix first.

Pepper’s pleasure in those tattoos—and he describes in some detail the enjoyment he derived from gazing at himself shirtless in the mirror—came from his self-proclaimed delight in the pain of implanting them on his flesh, but also from the simple fact that tattooing was strictly forbidden at San Quentin. You could end up stark naked in solitary confinement as a result.

If you couldn’t decipher Pepper’s bio from the images, he happily filled in the details. “At the age of 15, I was a complete alcoholic,” he told one interviewer, “and by the time I was 22, was as strung out on shit as you can get.”

“Each year his reputation moved up a notch until finally, in 1951, Pepper finished just 16 votes behind Charlie Parker in the Downbeat poll.”

In fact, Pepper left behind a whole book filled with truth-telling of this sort, the incomparable but deeply disturbing Straight Life, co-written with his wife Laurie and published three years before the saxophonist’s death in 1982.

That was the end of his final comeback. As I count them, there were four in total.

So many times, Pepper seemed on the brink of crossover fame—but things always fell apart. The first break happened when, just a teenager, he got hired by the Stan Kenton band, and started making a name for himself. But a year later Pepper was drafted into the Army, and sent overseas to fight World War II.

Two years later, Pepper returned to Kenton, and now his impassioned saxophony really shook things up. If you heard Pepper in concert, you walked away convinced of his star potential. And each year his reputation moved up a notch until finally, in 1951, Pepper finished just 16 votes behind Charlie Parker in the Downbeat poll—despite never showing up in those New York clubs where jazz reputations are made.

But a few months later, the Feds nabbed him on drug charges. Pepper was sentenced to two years in prison.

Upon his release, Pepper proved he could play better than ever. But he hardly had a chance to re-establish himself before getting arrested again—for possessing codeine along with telltale needle marks.

At this juncture, Pepper had been using 40 caps of heroin a day. His weight had dropped to just 128 pounds. In an interview with John Tynan for Downbeat, Pepper later speculated that, if he hadn’t been arrested, he would have “been using maybe a hundred caps a day in another month, if I had access to that much—because the demand just builds and builds.”

This time he spent more than a year in LA County Jail and the penitentiary on Terminal Island. From the prison—situated midway between the ports of Los Angeles and Long Beach on a strip of land once known as Rattlesnake Island—Pepper could see the neighborhood in San Pedro where had grown up. Even the same foghorn he heard as a child, now echoed through the penitentiary at night, reminding him of how far he had fallen from grace.

When Pepper came out after his second incarceration, few in the music world wanted anything to do with him. He was a two-time loser, and another arrest could send him to prison for decades. But Les Koenig of Contemporary Records remained a loyal advocate, convinced that this former convict was the best alto sax player on the West Coast. Koenig, to his credit, never lost faith in Pepper’s ability, and shortly before the producer’s death in 1977 helped mount Art’s final comeback.

But on this earlier occasion, Koenig got carried away. Without any advance warning, he hired Miles Davis’s rhythm section, then performing in LA, for a one day record session in January 1957. Pepper would front the hottest rhythm section in jazz, and show the world his greatness.

That was the plan. However, there were a few problems.

First, the session was arranged on short notice—so there would be no chance for a rehearsal. Pepper, for his part, hadn’t played the horn in many days (or months, if you believe his own account). And one last thing: Koenig was afraid to tell Pepper, worried his star saxophonist might back out if given too much time to think about the gig. So the leader of the date was the last to learn about it.

As it turned out, Koenig didn’t notify Pepper until the morning of the session. By now it was too late to cancel. Red Garland, Paul Chambers, and Philly Jo Jones had already been hired, and would soon arrive at the studio.

“I got my horn out of the closet and looked at it, and it looked like some stranger,” Pepper later recalled.

He continues:

It looked like something from another life. . . . And I was going to have to play with Miles Davis’s rhythm section. They played every single night, all night. I hadn’t touched my horn in six months. . . .There was no way to fix the neck, so I put the mouthpiece back on it with the cork and fitted it where it was. If I wasn’t in tune, or if it started slipping or pulling loose or leaking, I was dead. I wrapped some tape around it. I took the reed off. It was stuck on the mouthpiece, all rotted and green. I got a new reed, found one I liked, and blew into the horn. Then Diana came to the door. . . .She said: ‘It’s time for us to go.’

Pepper not only survived this trial by fire, but delivered one of the classic albums of the era. People were soon talking about him again, and a series of follow-up recordings for Contemporary sealed the deal. This was music you couldn’t ignore. If you were a jazz fan, either you knew about Art Pepper, or would soon find out. 

Pepper, always restless, was also taking more risks with each album. An intense, probing sound gradually grafted itself on the innocent, romanticism of his early work. At the start of the new decade, his 1960 album Smackup hinted at this more expansive phase, a higher level of playing where he could somehow merge West Coast cool with the clamorous sax insurgency coming from Coltrane and Ornette.

Around that same time, Downbeat ran an article entitled “The Return of Art Pepper”—journalists could use that headline for pretty much any article on this artist—hailing a comeback that, once again, proved all too short-lived. On October 25, 1960, Pepper was arrested while trying to buy heroin. As a third-time offender, Pepper got sentenced to two-to-twenty years, and placed in San Quentin, home for the most violent offenders in the state prison system.

Smackup was recorded in 1960 shortly before Pepper’s time in San Quentin, and Art Pepper Today was a comeback album from 1978

Even after his initial release from San Quentin—a three-and-a-half year stint—he kept getting sent back for parole violations. As it turned out, the hottest alto player out West spent most of the 1960s in prison. And even after his final term inside, Pepper opted for residential treatment at Synanon, a cult-like program for addicts in Santa Monica—where Pepper simply substituted one form of institutionalization for another.

Art Pepper was 44 years old when he entered Synanon, and lucky to be alive. His spleen had ruptured, requiring emergency surgery and removal. His stomach hernia, in contrast, was deemed inoperable. His liver was in even worse shape—Pepper suffered from cirrhosis, exacerbated because he continued to drink after the diagnosis.

Hey, there was one good sign: His hair hadn’t gone gray—and wouldn’t during his remaining years. But that was the only remnant of Art Pepper’s once smoldering good looks. (“I could probably have been a movie star,” he notes at one juncture in his autobiograpy, “or a great engineer from Cal Tech.”) Another positive: He met his future wife, Laurie Miller, age 28 at the time and also a resident at Synanon. She presided over Pepper’s final, and most majestic comeback, and worked to ensure and advance his posthumous influence, even launching a record label appropriately named Widow’s Taste.  

At first, it didn’t seem like there would be any more chances for a jazz career. Pepper had worked in the paymaster’s office at San Quentin, and now spent more than two years handling bookkeeping at Synanon. When he finally moved out of the facility—because the new rules forbade cigarettes, a final demand Pepper refused to accept—he started working long shifts at a Venice bakery.

Could he return to jazz? Pepper had taken a few gigs after his release from prison, and even toured briefly with Buddy Rich’s big band. But most jazz fans simply forgot that Art Pepper had ever existed. A few might have heard about his long sentence in San Quentin, and probably wrote him off as a lost cause. A handful of others might still wonder about the glamorous horn player from the old days but, for them, it was almost as if Pepper had vanished in his early 30s. They weren’t ready for him to return, a wounded survivor covered with prison tattoos, in his 50s.

Adding to those issues, Pepper now played differently. In his early days, fans loved his melodicism and sweet sax sound, but during those lost years, Pepper had assimilated Coltrane and the avant-garde into his vocabulary. For a while, he even switched to tenor sax, so powerful had Trane’s influence become.

Yet somehow the romanticism persisted, despite all the suffering—the end result was a paradoxical jazz style, dreamy innocence that could veer in an instant into strident outbursts. Unless you heard it, you wouldn’t believe such contradictory possibilities could coexist in a single song. The few faithful fans who still remembered Art Pepper from the 1950s were in for a shock when they heard him in the late 1970s.

And seeing him could be disconcerting too, especially if you remembered Pepper’s movie star good looks from the glory years post-Kenton and pre-Quentin. His face now had the pale unhealthy look of someone who had never seen the sun, or at least not for a decade or so. His gaze was hollow and emotionless, strangely out of whack with his impassioned playing. Even when he smiled, Pepper’s face never really lit up—it was as if he had seen too much, and was putting all his energy into trying to block out the memories.

That was Art Pepper when I first encountered him—initially on record, then in live performance, and finally in an interview, the last he gave before his death. And if you judged him on the basis of his appearance alone, you would never guess he could make one more comeback.

But you only needed to hear him play, and you realized that—somehow, against all the odds—he was better than ever. I try to avoid jazz clichés about suffering and dues-playing, but with Pepper you can’t avoid it. He was like a Dante who had come back from the Inferno, and brought some of its fire to share with us.

After those glorious albums of 1955-1960, almost 15 years would elapse before Art Pepper got signed by a label for another leader date. Once again Les Koenig at Contemporary gave the go-ahead for that final ‘return’ of Art Pepper. Yet now the altoist was haggard and broken physically, looking much older than the fifty years he had under his belt when Living Legend, his 1975 comeback album came out.

But if you didn’t know it already, let me tell you: Looks are deceiving. Lordy, Pepper could still play. He hadn’t lost the gift.

Where did it come from? “I’ve never studied, never practiced,” he once explained. He did things “off the top,” as he put it. That might be an exaggeration—Pepper often got caught up in his own mythology—but only a slight one. You just needed to watch him on the bandstand, and you could tell he was drawing on some inner force, something deeper than what you can learn in a practice room. Because, sure as hell, they don’t teach what he did in any music school.

People who fell under his sway back then all have their story about the moment when Art Pepper shook them to the core. For me, it was “Patricia” on Art Pepper Today, his debut album for the Galaxy label from 1978, where he torches everything in sight, especially in the final 60 seconds—and all he needed was a two-chord vamp to close a gentle ballad. 

My personal theory is that Pepper knew that this was his last chance, and didn’t want to be denied. He couldn’t afford the luxury of settling into a comfortable old age—he still wanted to prove himself. He desperately wanted it.

In my interview with him—just a few days before his death—Pepper spoke about missed opportunities, but even more about all the things he still wanted to do. He told me how much he wanted to see his picture on the cover of Downbeat (so typical of Art to give voice to these kinds of things) and also got enthusiastic when I asked him about other records he would like to make. He started talking about doing something with Toshiko Akiyoshi or a bluesy down home record or maybe a solo sax project.

None of this ever happened. Not the cover photo or any of the sessions. Pepper suffered a stroke on June 15, 1982. He was 56 years old—young by most standards, but an old man when you gauged all the wear and tear on that ornamented body.

But he recorded prolifically during the last five years of his life, and at a consistently high level. I have favorites among these albums—the early Galaxy recordings with George Cables and the Village Vanguard tracks with Elvin Jones, for example—but the simple truth is that you can listen to almost anything Pepper recorded during those final years, and walk away a believer.

He left us too soon. But, in truth, just surviving to make that final comeback was a miracle, given his heedless behavior and risk-taking. You could meet a thousand people, and none of them would be as dangerously in-the-moment as Art Pepper.

If you want to learn more about Art Pepper, I recommend these four books

Here’s a final story. At his lowest point, when he was committing armed robberies to support his habit, the other gang members refused to let Art Pepper hold the gun—despite his insistence. They might be violent, hardened criminals, but even they knew that this jazz musician was much wilder and less predictable than any of them.

It’s the oldest cliché in the music critic’s arsenal, but it’s true. This fearlessness and total spontaneity destroyed Pepper’s life, but also made him into a fire-breathing improviser on the bandstand. Maybe all that dues-paying stuff is just a tall tale to you, but for me, that’s the only way to take full measure of the four comebacks of Art Pepper.

He lived on the edge, and took the punishments it brought him. Against heavy odds, he survived, and even as his body weakened, he somehow got stronger psychically. And, finally, he drew on all this to make music, incomparable music.

If you want to separate these details into isolated boxes, go right ahead. But, for my part, I buy into the whole mythology of Art Pepper, the entire legend, so dauntingly large, down to that last symbolic icon on his illustrated man torso. But to his credit, Pepper’s music is far larger, and may prove, with the verdict of time, even more legendary than the man.