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Jake Brennan
Double Elvis.
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Jake Brennan
Disgraceland is a production of Double Elvis. Heads up guys. In this episode there's a lot of talk of the mid century concept of cool as well as about heroin. It should go without saying that there is nothing in this episode that is an endorsement of that drug. Or any drug for that matter. But you're smart enough to know that already. All right, let's get into it. The stories about jazz musician Chet Baker are truly insane. He was a natural gifted musician with a mile long rap sheet. He was worshiped by beautiful movie stars and both loved and loathed by serious jazz contemporaries. He was heavily addicted to heroin and made heavily addictive music. Chet Baker, with his overtly romantic style of playing and singing, coupled with his matinee idol good looks, was called the James Dean of Jazz. He was also called many other things. Gifted junkie, angel, scammer, cool, stupid, charming, abusive, beautiful, and a rat. He was indeed all of these things. And he did of course make great music. That music I played for you at the top of the show, that wasn't great music. That was a preset loop from my melotron called second story swing mk1. I played you that loop because I can't afford the rights to Wishing well by Terence Trent Darby. And why would I play you that specific slice of hardline cheese? Could I afford it? Because that was the number one song in America on May 13, 1988. And that was the day Chet Baker lost his life creating one of the most Enduring Mysteries in Music. The cause of his death. On this episode, Hard Bop Heroin, Hardline Cheese, the James Dean of Jazz, and Getting Lost with Chet Baker. I'm Jake Brennan, and this is Disgrace. The smack to the mouth stung, but he said nothing. His mother looked on in horror, but she said nothing. His father, who gave him the crack, said said nothing as well. Nobody said anything. They were too busy trying to keep their cool. The house was a powder keg of suppressed tension. The tension was always there, just like those Oklahoma clouds. They never seemed to pass, even when the sun fought its way through. The clouds hung around, ensuring that the sky would never be more than just almost blue. The humiliation would never fully pass either. Even as an adult, even in success, even with the adoration of jazz lovers up and down the west coast, whenever anything good would happen to him, there was that familiar pull in the back of his mind. It blasted into his conscience like hard bop, demanding to be heard. It said, remember me, pretty boy? I'm here to remind you that you ain't shit. You ain't cool. You ain't ever been cool, and you ain't ever gonna be cool. You're gonna be just like your daddy. Some jive ass half a musician who can't find work, who nobody ever heard of. When Downbeat magazine, the paper of record for jazz aficionados, named him Chet Baker, Trumpeter of the year two years running back in 1954 and 55, there was no joy he beat out Miles Davis. He knew what that meant. Resentment and anger for something he couldn't control. The color of his skin, White. So very unhip. When he met Miles, he told him straight up that he wanted to write him a letter apologizing for winning the award because he knew he wasn't better than Miles. Miles said, you got about 15 other letters to write before you get to me. The sting of the rejection from the hippest musician on the planet was the same, if not worse, than the sting of the beatings he took from his old man. Like Miles, the old man was not short on resentment and anger. The drugs helped. Heroin, grass, whatever pills he could get, but mainly heroin. The drug, shooting it, scoring it, occupied every waking moment. He wasn't on stage, and in 1966, the stage wasn't bringing in the bread like it was back in the mid-50s in Los Angeles. In New York, his reputation as a serious jazz man was eclipsed by his reputation as a dangerous drug addict. And so road work was necessary. Scoring depended entirely on what city you were. In this city, wherever the Fuck USA was not hip. He needed to come up with a new plan. To catch a thief with Cary Grant, the Hitchcock movie. Grant, clad head to toe in black night, crawling throughout the Italian Riviera, in and out of unsuspecting socialites windows, robbing them of their jewelry and cash. Chet thought he could have been cast as the thief over Grant. He knew Italy like the back of his hand and he would have been able to do his own stunts. He was a righteous second story man. Next to blowing trumpet and crooning, scamming people was one of his greatest talents. Particularly breaking and entering above the ground floor. The crime spree he and his bassist Bob Whitlock had embarked upon was necessary. Without junk, they would be rendered useless, bedridden with violent withdrawals and unable to perform. Which was the whole point of being on the road in the first place. Put in work, make the bread. Except all the bread went toward heroin and when it ran out, there were no options. Chet's habit was extreme, to say the least. He'd have to improvise. Whitlock looked on in amazement as the great Chet Baker scaled the fire escape. He then hemmed his body tight to the side of the opulent home on the second story and carefully placed each foot on the ledge of the home's massive window nearest the fire. Fire escape. He popped the lock, lifted the glass, pushed his wiry body through and was in and out with the valuables in no time. They'd cool their jets at an all night diner and wait for the pawn shop to open. When second story work wasn't an option, I. E. They couldn't wait on the sun to come up in the pawn shops to open and the dealers to wake up. They'd work their drugstore scam. Chet had it down pat. All that acting over in Italy had paid off. First he'd prick his finger and draw blood into a tiny vial. And then he'd hit the local pharmacist's up with his plate. Gee doc, I don't know. Hurts when I move and my gut hurts when I pee too. Maybe it's a kidney stone, I don't know. And the pharmacist would have Chet give a urine sample. Chet would drop a couple specks of his own blood from the vial into the urine and voila. A dilated prescription and a passable substitute for heroin. The scam didn't end there. While Chet was performing his little one act on the good doctor, Whitlock would sidle up to the counter all nonchalant and Work his charm on the nurse. And if she was easily flattered, which was usually the case, he would manage to get his sweaty paw on the doc's prescription pad. And from there it was off to the races. But it wasn't always about the drugs. In the beginning, it was about the music. Chet Baker was a lot of things, and stupid might have been one of them. It was little thought that went into his playing. When people who knew him as a man and as a musician speak of him, they almost always reference his natural talent. The music seemed to flow right through him, often at lightning speed and in tight, perfectly natural, impeccably timed phrases. It was a style that other jazz trumpeters practice rigorously to achieve. But none of them ever saw Chet practice. He'd just show up and blow. He cared, but not enough to rehearse, or so it seemed. And this detachment, along with his natural talent and striking good looks, lent an air of cool to Chet Baker's Persona that wasn't previously seen or heard in any musician anywhere, in any genre. In the 1940s and 50s, for jazz musicians and fans, particularly those being swept up in the thrill of a new type of jazz called bebop, being vanguarded by the great jazz musicians Dizzy Gillespie, Charlie Parker, in the aforementioned Miles Davis, the concept of cool meant you were different, you were apart from the rest of society. Cool was a way of life. Cool, it was said, meant that you get done in a sentence what somebody else would get done in a paragraph. Cool was an economy of effort in life and in one's playing. Miles Davis was cool. Cool was ice, Cool was intellectual. Cool was black. But Chet Baker was warm. Those soft eyes and romantic melodies. Chet was a lot of things, and intellectual was not one of them. And Chet was white. Yet Chet was still somehow cool. Charlie Parker said so. And Charlie Parker knew from cool. He, along with Dizzy Miles, drummer Max Roach and pianist Bud Powell, were among a handful of musicians on the east coast who were literally revolutionizing music, taking swing music and pop single standards and ripping them inside out. Preserving little of the original compositions. These players would demolish the song's melodies, using only the chord progressions as the road forward upon which they would blaze. Manic, furious, improvisational melodies and solos. And bebop horn players blew hard. The great Louis Armstrong, the father of jazz, had no idea what he was listening to when he first heard it. Few others did either. Only those who were cool got was a badge of honor, a sign that you were cool. If you were into bebop, shooting heroin further cemented your status. Bebop musicians, Charlie Parker especially, were largely hardcore savage junkies. Heroin took one's disaffected attitude toward life, toward society, toward everything, and rooted it into something real and dangerous. Nothing signaled to the straight world you, your hipness, your otherness more than your heroin habit. It blocked out the harshness of white conformist, post World War II America and heightened the only part of the day that mattered, the only part of the day that you weren't high on narcotics when you were on stage tearing apart tradition on the icy, cool wings of improvisation. In the early 50s, the only thing cooler than being into bebop and being on heroin was being black. Chet Baker did not play bebop. He played straight. Chet Baker was not on heroin. His drug at the time was reefer, and he was again, obviously not black. He wasn't even from the East Coast. He was from the not very bebop West Coast. Yet that didn't stop Charlie Parker from hiring Chet Baker on a West coast stint in 1952. Such was Chet's immense natural talent and disaffected cool charisma. After Parker's engagement at point one run its course, during which Chet further proved himself to his hero by personally scoring dope for him on a regular basis, Parker called Dizzy Gillespie back in New York. His message was short and to the point. You better look out. There's a little white cat out here who's going to eat you up.
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I buy my clothes the same place I buy my groceries.
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Chet Baker stood on stage and the rest of the quartet eased into the ballad's intro. Chet's head was down, chin pressed to the top of his chest, trumpet hanging off to his right, waiting not for a cue, but for that feeling. When it came, he lifted his head and positioned his lips to the end of the microphone, so close they touched. He clinched his eyes together hard, blocked out the rest of the band, the audience, starlets, boppers and hoppers among them. And the muscles in his face tightened while he listened for the right note. It was there and then it was gone. Lost stone still, he waited for the chord progression to loop back around, for another opportunity to ease into the romance afforded by what was one of his favorite melodies. When it came, he opened his mouth to sing in a whisper so vulnerable it stunned the audience into silence for fear of what any unintended distraction on their part might do to the beautiful and wounded artist on stage. His trumpet playing may have been natural, but. But his voice was much affected, though in such a way that it seemed, of course, natural. Chet Baker knew what he was doing. As a horn player, he knew about controlling pitch, so as a singer, he was able to manipulate the pitch of his own voice, a concept that likely never occurred to traditional singers. It was subversive, a sensibility owed to his love of bebop, a genre he admired but seldom played, opting for a more traditional style of jazz that suited his natural talent and, well, laziness. But when it came to singing, Chet would consciously manipulate the pitch of the melody he was singing, causing his vocal line to be, as he would later say, under the center of tonality, to square as it sounded wrong. To those with ears, however, it sounded entirely unique and created a beautiful sense of intense vulnerability. Chet Baker whispered his vocals softly and intentionally, and the result was such that he felt as though he was singing to you and only to you. You were alone together. Chet Baker's vulnerability is such that it makes you feel vulnerable. More than any other musician, Chet Baker, when he's on, sends you reeling. His music creates a sense of wooziness and emotional vertigo where you lose yourself in the spell of Chet. It's everything about him. His voice, his playing, his vulnerability, his addiction, his myth. It detaches you. Chet sings that old saloon song, everything happens to Me and you're naked. Untethered from your resolve and in need of a good cry. Or at the very least, the warm embrace of a beautiful, understanding Italian lover. You know, like Chet. At least that's how Marilyn Monroe felt. And Jane Russell. And even Jane's friend, professional hard ass Robert Mitchum. They were all in the audience on that night. Mitchum knew about bad luck, his life experience to that point. A 14 year old runaway turned shoe salesman turned Hollywood star, Tinseltown's first real life bad boy, both on and off screen. Tall, dark, handsome, brooding, often drunk, arrested and shipped off to World War II as punishment, only to return to a reefer bust in 1948. Mitchum was not your friendly neighborhood banker. He was not Jimmy Stewart. Bob Mitchum was a real life antihero who could easily pick up the burden. Chet Baker was putting down. This despite the fact that Mitchum was Hollywood's Masculine archetype, handsome and strong, with a deep baritone. And Chet Baker was the opposite. Pretty and sensitive with a tenor singing voice far more James Dean than John Wayne. Didn't matter. Chet Baker's playing, his image, the rumors of his notorious drug habit, the growing myth of his cool, all that subversiveness. Bob Mitchum was hooked. And Jane Russell, like Bob and Marilyn Monroe, would listen to anything Jane said. So they, along with a club full of Hollywood elite, all wound up at the Hague nightclub one night in April of 1953. So, too, to Detective John Edward O' Grady's scourge of hoppers, bobsters and jazz heads. Throughout Los Angeles, dangerous musicians and celebrity drug addicts like Robert Mitchum and Chet Baker were public enemy number one for o', Grady, leader of the LAPD narcotics squad, who had pledged that the, quote, dream of his life was protecting society against the creeping menace of drugs. To o', Grady, being a narcotics detective wasn't a job, it was a crusade. He cast himself into his own starring role as savior to the good, straight, hard working people of 1950s Los Angeles. He wore his crew cut high and tight. He wore his dark sunglasses inside and out. And he wore his pearl handled revolver proudly on his hip as he patrolled Hollywood Boulevard, calling himself the ball busting Sergeant o'. Grady. The big time big O daddy O, the most feared cop in the city, the meanest motherfucker on the fourth scourge of the drug scourge. And he hated Chet Baker as much as he hated Bob Mitchum. He trailed Mitchum to the Hague and that Baker was playing as part of the fashionably hip Gerry Mulligan Quartet. As a bonus, two for one special, one reeferhead and one Junko. And one night, if o' Grady was lucky, he and his men positioned themselves as inconspicuously as they could within the crowd, which is to say, not very conspicuously at all, given their square haircuts, white socks and black shoes. But it didn't matter. O' Grady had a devious play with the band. Distracted on stage, he dispatched some of his squad to Jerry Mulligan's house, where they entered without a warrant and intimidated Mulligan's and Baker's girlfriends into giving up whatever illegal drugs they had, which was marijuana, which at the time in California carried a stiff prison sentence. O Grady's men brought the girls back to the Hague and after the set, they wrangled them and their museum musician boyfriends into the back room office to grill them on where they kept their stash. Chet Baker played it cool. Jerry Mulligan, perhaps in the throes of a heroin jones, broke down crying. O' Grady noticed the track marks on his arms. He and his men drove the musicians and their girls back to Mulligan's for a proper search, again without a warrant. And scared Mulligan into giving up his works and his heroin stash. And they were all busted it. The following day, the headline from the Los Angeles Mirror screened hot lips bobster 8 and 2 wives jailed nab dope. The headline and article were accompanied by a photo of Chet Baker, who of course, looked undeniably cool. We'll be right back after this.
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Chet skated from the bust. It was Jerry Mulligan's dope after all. Jerry went to jail. Chet felt invincible. He was the great Chet Baker, the coolest daddy. Oh, so cool that Hollywood opened its arms for real. Chet made his acting debut in the war film Hell's Horizon. Then he was offered a movie studio contract. The idea was he'd be the next Sinatra by way of James Dean. The James Dean of jazz, baby, a new type of screen star. But Chet declined. Movie stars were decidedly uncool compared to jazz musicians. It continued to blow for his bread. After filming for Hell's Horizon wrapped, Chet hit the road. Carnegie hall in New York with Dave Brubeck. The staunch east coast jazz critics bucked. Movie star. Jasmine didn't play. Chet banged more dope into his arm. In Boston, Chet allowed a young jazz pianist, Dick Twarzik, to sit in with him in and afterward. Chet Baker would never be the same. Dick Twarzik's playing seemed to embody, well, everything. It was steeped in classical, yet unafraid to flirt with the avant garde. His approach to harmony was unmatched emotionally. It was deep and cutting and his playing incredibly soulful. He achieved a trance like state on stage. His whole vibe as a musician, as a man, smacked of euphoria. Chet Baker was in love. Dick Twarzik was everything he was not. Chet was soft. His music was as. He was approachable. Dick was hard, mysterious and Egon Shield portrait come to life. Sprung from the cafes of Paris in the twenties, a long way from Chad's Oklahoma. Chet was a simple melodist, Dick a complex harmonist. Immediately, Chet loved playing with him. Dick was going to forever change the that fact, the face of jazz. Everyone knew it. And it lent an extra air of cool to Chet Baker. Chet was hip squared with Dick, on stage with him and off stage, Chet vibed all over Dick's personality. Dick compensated for Chad's shortcomings. He fulfilled something in chat. Those who knew Chet Baker best, his longtime girlfriend later in life, Ruth Young, swear Dick roused Chet's latent homosexual feelings. And of course, Dick shared check Chet's fascination with heroin. The euphoric highs Dick achieved with his playing seemed to chat to only be possible through junk. Together, the two collided into their own kind of lost chord. Heroin harmony. The stint in Boston only lasted a matter of days, but Chet felt he had made a friend for life, left Dick behind and continued his tour. Dick remarkably got clean, completing rehab and kicking junk altogether. But before the year would end, Chet Baker came calling with an offer for Dick to join his band on a tour of Europe. Dick accepted. Dick's girlfriend knew in her gut that it would be the last time she would see him alive. She was right. It took literally minutes upon his departure with Chet and the rest of his band for Dick to succumb to that old habit. In no time, he was hooked again. On the night of October 20, 1955, in Paris, Dick Twarzik played his last gig with Chet Baker, the last gig of his life. He returned to his hotel room, locked his door, and proceeded to jack a gluttonous amount of junk into his arm. When they broke down the door and found him the next morning, the needle was still sticking out of his arm. He was 24 years old, dead in blue. Chet was in shape shock. Those who knew Dick, including members of Chet's band at the time, were angry. Chet's then drummer, Peter Lippman, had his own version of what happened, and it involved Chet going back to Dick's hotel room with him shooting up and bailing in a panic after Dick began to od. Concerned about more bad press and his already dwindling career opportunities, Chet Baker, Litman alleged, ran out on a dying friend. Chet's reputation took a massive hit hit, a metronome, even hinting in its pages that Chet was somehow responsible. Dick's parents wrote Chet countless letters blaming him for their son's death. Chet Baker was ravaged with guilt and for his part, had no real answers as to what actually happened that night. Unbelievably, he claimed, among other things, that he was actually clean at the time and had no awareness of Dick's habit. Chet gave numerous accounts to different people over the years, each eventually arriving or hinting at Chet somehow being victim. Chet Baker forever cast as the lost lovable loser in his own saloon song. Regardless of who was to blame, loss crushed Chet Baker he returned to America to find work, to New York City, the heroin capital of the world. And there was little work for him upon his return. The only people who were cared about Chet Baker's arrival in New York City were the drug dealers at the five Spot nightclub. Dirty Nick, Johnny E, Slim and Ray with the blonde hair. Serious bebop heads were preoccupied downtown with Miles Davis, who just released his incredible album Miles Ahead, as well as with the now legendary East Village live residency of Thelonious Monk and John Coltrane. They could care less about some white west coast trumpeter who made more headlines with his drug use. And he made heads turn with anything resembling innovation. Chet skulked in the shadows, hustled dope on money borrowed from friends or took it on the arm from the dealers. And when the goodwill at the five spot would dry up, he'd hit Hansen's Drugstore on 51st and 7th to score. That is only if he could pry the attention of the dealers away from comedian Lenny Bruce, who'd set up shop in the back, his own private clubhouse, a drug store. Lenny Bruce may have been ahead of his time, but his sense of place was beyond brilliant. For Chet Baker, not so much. There's another heroin bust and then another Baker to satisfy the judge committed to cleaning up in the legendary rehab facility in Lexington, Kentucky. He made good on his promise, moved right back to New York, settled in with a prostitute friend named Pixie and her street hustler roommate, and quickly got back on the horse again. Remarkably, with his reputation in near tatters, some of the greatest jazz men of the era agreed to a recording session with Chet, the great pianist Bill Evans and incredible guitarist Kenny Burrell among them. Chet was something approaching professional in the face of these modern day giants, and he delivered, creating one of his best studio albums, 1959's Chet. But the creative success was unsatisfying his demons, be they driven by the guilt and shame of Dick Twarzik's death. The rejection he felt from the hardcore bebop set, the sting of his father's abuse, or just his own reckless detachment were going to get the better of him. And Chet Baker was determined to lose himself. 1959, 116th in Lenox, Harlem. The spot to cop. The junkies knew it, the dealers knew it, and the cops knew it too. They also knew that if you were white, you stayed far away from this corner in Harlem. Chet Baker apparently didn't know this, or didn't care, or was too stupid to understand. Either way, he was an easy mark and he was Busted while on bail, he went back uptown to Harlem to score. And of course, he was busted again just two weeks later. Rehab, this time would be received only at Rikers Island East River Detox. Welcome to hell Ship bird. Chet cleaned up. He had to, in order to survive. Kicked, worked out, got himself back into shape, and because of his physical attractiveness, he did what was necessary to survive in a racially divided 1950s prison. Chet Baker, in order to avoid the notorious Rikers Booty Bandits, the rapists who congregated in the prison showers where so much for sex took place that the stank of semen was constant, moved into a black inmate cell, a much larger black in me. Chet then began hanging out exclusively with black inmates. One inmate later recalled that Chet would hang in the yard and stretch out for some sun, laying his head in his roommate's lap, staring lovingly up into his eyes. Chad's friend Jack Simpson recalled that upon release, Chet remarked that his roommate protected him, loved him, and they quote, he would have fucking died for me. Chet Baker survived Rikers, but now free, the question was, would he survive himself? After prison, Chet Baker abandoned America. Perhaps sensing it was about to abandon him, he settled in Italy, where he was beloved as l', Angelo, the Angel and Trompa d', Oro, or the Golden Trumpet. Italy, with its love of glamour and grime, loved Chet Baker. And so too did their infamous paparazzi. It wasn't long before drug officials got hip to Chet's heroin jive, and he was busted again for narcotics. The trial was national news, during which Chet's defense attorney presented evidence in an effort to appeal to the court's pity, depicting Chet as a victim of heroin, going so far as to tell the story of Dick Toard's ex girlfriend slapping Chet in the face and accusing him of killing her boyfriend. Chet was traumatized, his attorney argued. Surely the court could sympathize and go easy on him. They didn't. Chet was sent to prison again. He did a year and a half, and by the mid-60s, with something more to support than a heroin addiction, namely a new baby and a wife, his third, Chet Baker returned to the States to find work. He wound up again on the west coast and was, of course, looking to score. All Chet Baker wanted to do was to score. It had been a rough night. The gig was awful, and his jones was strong. It was early morning. San Francisco was waking up. Chad hit the CD hotel in the Fillmore to cop. In the hallway, he came upon the dealer. Chet gave him the knowing nod, and the dealer Just stared at him. Then, according to Chet and numerous recountings of the story, five guys came up behind the dealer from the back of the hall. The dealer said nothing, just walked backward. Chet turned to run and the five dudes broke into a sprint out the door onto the sidewalk. One of them got his hand onto Chet's shoulder in mid sprint and spun him around. Chet maintained his balance, caught a fist to the grill. He swung back toward them him while continuing to move backward. All five guys now punching and kicking him in stride. Chet compelled them in a slow motion backward ball of violence. Fists, feet, fury flying from all. Chet stumbled backward into a newspaper stand, grabbed it, shoved it toward his attackers. One of them tripped. Chet stumbled back some more into a parking meter that halted his progress. He took a sharp fist to the cheek. It had the opposite effect. It was supposed to have it invigorated. He fought back, harder, faster. Another one of his attackers hit the pavement from one of Chad's haymakers. Two down, three to go. And the brawling foursome continue their backward progression. Chet continued landing shots in defense. He stumbled into a parked sedan with four people inside. He climbed on top of the car. His attackers swiped at his ankles. Chet hot stepped around their grass, alternately stomping on their hands. One attacker attempted to climb up on the back of the the trunk. Chet booted him in the face, sending him reeling. Three down, two to go. Chet leapt to the street side of the car, opened the backseat passenger side door to the shock and horror of the car's passengers, and dove in, screaming to the driver, who he did not know, to step on it and get him the out of there. The driver did no such thing. Chet pounded on the back of the seat. The dude next to him reached across Chet's body, opened the door and pushed Chet out onto the street, where now all five of his attackers had no reassembled. Chet landed on the pavement on his side. The men surrounded him. And then the real beating began. Repeated kicks to the head, face and the body. Chet was lost, no idea what was happening. The kicking stopped. One of the men told another to roll him over. Let me see his teeth. Chet was rolled onto his back, his face a bloody mess, barely conscious, his head rolled to his side, his cheek on the pavement. One of the attackers anchored his left leg solid into the ground, pulled his right leg back and hauled off, and with all the strength he could muster, kicked his foot straight into the trumpeter's mouth, shattering his teeth. When they found Chet Baker, he was passed out in a pool of his own Urine and vomit. His teeth were shattered. All of them were so badly damaged that the ones that didn't remain were required to be pulled. A trumpeter can't blow his horn without his teeth. The shape of a trumpeter's dental structure, their embouchure, accounts for part of the player's delivery. Without teeth, it is near impossible to play a wind instrument. Chet Baker was done. And as far as the dealers in San Francisco were concerned, this was a good thing. Chet was suspected of being at best a scamming junkie who couldn't make do on his debts or promises, and at worst, a rat who was selling out fellow junkies and dealers to the cops in order to avoid arrest and more jail time. Whoever was behind the beating of Chet Baker knew what they were doing. Want to get payback on a dirty trumpet player? Take away his teeth. Chet spent the next three years of his life pumping gas in California. 7am to 11pm the hardest work of his life, he would recall. Eventually he put the scratch together to get dentures he wanted back in. Dizzy Gillespie put together some work for him in New York City, and the rebirth of Chet Baker had commenced. A success in New York, he departed for Europe again, where he was beloved. He supplemented his heroin habit with methadone. He fell into some sort of working junkie groove, for the most part avoided the law and continued to make music into the 80s, where a new generation of hipsters discovered his incredible talent through a creatively fruitful collaboration with Elvis Costello. Chet Baker was living in Amsterdam on the second floor of the Hotel Prin and Drake. He was lost in the romance of his newfound relevance and attempting, as always, to get lost. His heroin use was back in full swing. May 13, 1988. Chet Baker walked into his hotel room after his gig, grabbed his works, injected himself with potent Dutch heroin, sat in the open windowsill of his second story room, dragged on a cigarette, nodded off and tipped over into the springtime air. He fell two stories and lost his life. May 13, 1988. Chet Baker walked into his hotel room after his gig, grabbed his works, injected himself with potent Dutch heroin, sat in the open windowsill of his second stone story room, dragged on a cigarette while the dealer he'd scammed burst through his door to push him out the window. He fell two stories and lost his life. May 13, 1988. Chet Baker lost the keys to his hotel room after his gig. His works were in his room. He needed to get high. He deployed his second story man skills, climbed out of his neighbor's window onto the balcony attempted to cross over onto his own balcony and lost his footing. He fell two stories and lost his life. Either way, Chet Baker was dead, lost finally for good. Remarkably, he'd made it as long as he had to the age of 58. The mystery surrounding his death survives as part of the myth of his cool and nodding off and falling out of the window and being shoved out of the window by an angry dealer are the two stories that get the most traction. But in reality, the story about Chet clumsily losing his balance while trying to scale the balcony is corroborated and likely the most plausible, if not the least romantic. So uncool. Such a Disgrace I'm Jake Brennan and this is the Disgraceland. Disgraceland was created by yours truly and is produced in partnership with Double Elvis. Credits for this episode can be found on the show notes page@gracelandpod.com if you're listening as a Disgraceland All Access member, thank you for supporting the show. We really appreciate it. And if not, you can become a member right now by going to Disgracelandpod.com Membership members can listen to every episode of Disgraceland ad free. Plus you'll get one brand new exclusive episode every month, weekly unscripted bonus episodes, special audio collections, and early access to merchandise and events. Visit disgracelandpod.com membership for details, rate and review the show and follow us on Instagram, TikTok, Twitter and Facebook Disgracelandpod and on YouTube@YouTube.com Disgracelandpod Rocka Rolla He's a bad, bad man.
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Host: Jake Brennan
Date: January 9, 2026
This episode of DISGRACELAND examines the tumultuous, myth-soaked life of jazz trumpeter and vocalist Chet Baker. Brennan explores how Baker’s legendary musical talent and heartthrob allure crash against his persistent self-destruction through heroin, crime, violence, and personal tragedy, ultimately painting him as the “James Dean of Jazz.” Listeners get the untold, darker tales glossed over in biopics—stories of outlaw cool, ruin, and the fatal toll of living on the edge.
(01:08–05:00)
“When Downbeat magazine... named him Chet Baker, Trumpeter of the Year two years running... there was no joy. He beat out Miles Davis. He knew what that meant—resentment and anger for something he couldn't control. The color of his skin. White. So very unhip.”
—Jake Brennan (02:40)
(05:00–12:50)
"Cool was ice, Cool was intellectual. Cool was black. But Chet Baker was warm. Those soft eyes and romantic melodies... Yet Chet was still somehow cool. Charlie Parker said so."
—Jake Brennan (10:28)
“You better look out. There's a little white cat out here who's going to eat you up.”
—Jake Brennan, quoting Parker (12:50)
(13:26–18:00)
“Chet Baker's vulnerability is such that it makes you feel vulnerable. More than any other musician, Chet Baker, when he's on, sends you reeling.”
—Jake Brennan (14:50)
(18:00–20:10)
(20:10–26:15)
“Chet's reputation took a massive hit, a metronome even hinting in its pages that Chet was somehow responsible... Chet Baker was ravaged with guilt and for his part, had no real answers as to what actually happened that night.”
—Jake Brennan (25:00)
(26:15–32:15)
“A trumpeter can't blow his horn without his teeth... Without teeth, it is near impossible to play a wind instrument. Chet Baker was done.”
—Jake Brennan (32:20)
(32:15–36:20)
“Either way, Chet Baker was dead, lost finally for good... Remarkably, he'd made it as long as he had to the age of 58. The mystery surrounding his death survives as part of the myth of his cool.”
—Jake Brennan (36:10)
On Chet’s style:
“He’d just show up and blow. He cared, but not enough to rehearse, or so it seemed. And this detachment, along with his natural talent and striking good looks, lent an air of cool to Chet Baker's Persona that wasn't previously seen or heard in any musician anywhere, in any genre.”
—Jake Brennan (08:30)
On the price of addiction:
“Heroin took one's disaffected attitude toward life, toward society, toward everything, and rooted it into something real and dangerous. Nothing signaled to the straight world your hipness, your otherness, more than your heroin habit.”
—Jake Brennan (09:45)
On loss and music:
“Chet Baker's vulnerability is such that it makes you feel vulnerable. More than any other musician, Chet Baker, when he's on, sends you reeling. His music creates a sense of wooziness and emotional vertigo where you lose yourself in the spell of Chet.”
—Jake Brennan (14:55)
On the legacy and mystery:
“The mystery surrounding his death survives as part of the myth of his cool… Such a Disgrace.”
—Jake Brennan (36:37)
Jake Brennan’s narration combines gritty detail, poetic prose, and sardonic “cool,” blending reverence for artistic struggle with the gallows humor and edge of true-crime storytelling:
“So uncool. Such a Disgrace.” (36:36)
Listeners are given a story as improvisational and unstable as jazz itself—punctuated by tragedy, betrayal, fleeting beauty, and the lure of danger.
Chet Baker’s story, as told by DISGRACELAND, is a wild improvisation—gifted, damaged, doomed, and endlessly cool, right up until the (still unsolved) end. For every note of romance, there’s a counter-rhythm of violence and addiction, making the beauty of his music inseparable from the danger and disgrace that defined his life.