This story appears in the May 2016 issue of Playboy. Subscribe

Nothing more influential than rap music
I merge jazz fusion with the trap music
I mix black soul with some rock and roll
They never box me in.

—Kendrick Lamar, “Black Friday”

These lines, taken from a freestyle that Compton artist Kendrick Lamar released in late November 2015, land between a riff about what the White House would be like if Kanye West took over and a slick comparison of Lamar’s DNA to the psychedelic drug DMT. As usual, the rapper delivers a blast of quotable lyrics across the track, but it’s the above salvo that sharply sums up Lamar’s To Pimp a Butterfly—the 2015 album that garnered him a historic 11 Grammy nominations—and the small, tight-knit cast of L.A. jazz musicians who helped create it.

Saxophonist Kamasi Washington, producer and saxophonist Terrace Martin and bassist Stephen “Thundercat” Bruner are all second-generation musicians, now in their early to mid-30s, who grew up together in South Los Angeles. (The L.A. City Council formally changed the name from “South-Central” in 2003 in an effort to downplay the area’s longtime association with gang violence, riots and poverty.) Their group dynamic is immediately apparent: Washington exudes a quiet yet larger-than-life gravity; Thundercat oozes otherworldly cool, offset by a sartorial style that includes pelts, traditional Native American headdresses and outer-space-inspired garb; and Martin, slightly older than the other two and often wearing an L.A. Dodgers cap, plays the role of seasoned streetwise leader.

Double-digit murder rates and gangsta-rap videos don’t tell the full story of the L.A. these artists were born into. Theirs was also a world of multi-school jazz bands and such venues as the World Stage Performance Gallery, a pocket-size arts space in the Leimert Park neighborhood that has hosted Herbie Hancock, Elvin Jones, Jackie McLean and Art Blakey. Founded in 1989 by drummer Billy Higgins and poet and community activist Kamau Daáood, the Stage provided a place for jazz musicians to learn from—and spar with—the greats.

The venue sits three doors down from the current home of the famed hip-hop open-mike event Project Blowed—a haven for groundbreaking MCs and the spot where Martin first fused his loves of hip-hop and jazz. Martin credits drummer Kahron Harrison with breaking down the barriers between jazz and rap artists in Leimert. “I was doing beats for the hip-hop cats, putting my horn up and pulling it back out when I got to the jazz club,” Martin says. “Harrison was going back and forth between the jazz and hip-hop clubs, playing drums for Aceyalone and Myka 9 from Freestyle Fellowship, Medusa and all them cats. I’d take my horn over there and play with them, and that was actually where this West Coast jazz and hip-hop shit started.”

Martin met Lamar when the rapper was still in high school. Anthony “Top Dawg” Tiffith, CEO of Top Dawg Entertainment, which would become Lamar’s label, had a small home studio in Carson, where he let Martin make beats. Lamar, Top Dawg producer Sounwave and rapper Jay Rock were also around, tending to their nascent careers. “We did a song together to get a deal at Warner Bros.,” Martin recalls. The title? “ ‘I’ma Tell My Mama on You,’ with Kendrick on the hook,” he says, laughing. “They’re gonna hate me if anyone ever hears that song.” Martin and Lamar have been tight ever since.

The scenes represented by the two men mingled in the crucible of a Los Angeles populated by working-class people, gang members and corrupt police. It proved to be a setting where players could compose and perform outstanding jazz music—and help create one of the most important albums in hip-hop history.

But before we get into that album, let’s review how jazz and rap came together in the first place.

The two genres, arguably America’s first and last true art forms, have enjoyed a rich if complicated relationship since the early 1970s, when DJs would cut the breaks from songs such as Bob James’s “Take Me to the Mardi Gras” and “Nautilus” at New York City park jams.

Before old jazz records became a go-to resource for hip-hop producers, the biggest rap records of the 1980s were largely derived from contemporary pop. But with Run-DMC’s early use of James’s songs and Eric B. & Rakim reintroducing James Brown’s funk on their debut album, hip-hop opened up a new lane for recordings that had mostly gone unnoticed by young people in the 1980s. Some established artists balked at the sample use, and rappers retorted—most notably the first hip-hop band, Stetsasonic, with its 1988 single “Talkin All That Jazz.”

We were influenced by all the greats, from Sly Stone to Miles Davis to Too $hort.

Even legal cases against De La Soul and Biz Markie in the early 1990s couldn’t stem the tide. Producers including Large Professor, Pete Rock, Prince Paul, DJ Premier of Gang Starr, and Ali Shaheed Muhammad and Q-Tip of A Tribe Called Quest made an art form of mining snippets of popular as well as obscure jazz records. The sonic references were not lost on astute listeners like Martin. “I remember listening to A Tribe Called Quest’s ‘Sucka Nigga’ and being like, Oh, that’s [Freddie Hubbard’s] ‘Red Clay’!” he says. “I continued to listen, and it really opened me up to liking jazz in a different way.” (In fact, Martin’s latest album, Velvet Portraits, includes the track “Tribe Called West.”)

Eventually rappers and producers worked directly with traditional jazz musicians. Legendary saxophonist (and notorious rap critic) Branford Marsalis tapped DJ Premier to co-produce his crossover album Buckshot LeFonque. Premier also contributed heavily to his late partner Guru’s Jazzmatazz series. Miles Davis’s posthumous album Doo-Bop, a collaboration with Easy Mo Bee, was the visionary trumpeter’s own version of hip-hop.

Since its inception, rap has gone from subculture to corporate juggernaut to some odd hybrid of the two, all while spawning countless mutations. Its relationship with jazz has withstood each era, less popular but just as potent, thanks to standout music from Madlib, the Roots, J Dilla and the Beatnuts. But it took Lamar and that small brotherhood of L.A. jazz players to bring it back to the forefront.

To Pimp a Butterfly pulls off the difficult task of sounding like every great black album we’ve heard and nothing else in existence. That was accomplished largely because the collective went into the studio with no thought of competing with the top 10 or with their peers. “We were influenced by all the greats, from Sly Stone to Miles Davis to Herbie Hancock to Quincy Jones to Dr. Dre to Too $hort,” Martin says. “As far as the concept, we were inspired more by life and what was going on around us than we were by music.”

Recorded over nearly two years, Butterfly tackles everything from police brutality to self-hate, depression to fame. Lamar taps into a vulnerability that is uncommon in rap, and the music matches his radical openness—largely because the players themselves were dealing with seismic changes. In a six-day period, Martin almost lost his father to a heart attack, and Zane Musa, a good friend and fellow L.A. musician, died suddenly.

Bruner (bass guitar), Martin (sax, middle), Washington (sax, right) and friends performing in Los Angeles last year.

“He was one of the top three saxophone players in the world, technically way better than me or Kamasi will ever probably be,” Martin says. “We didn’t have time to pop bottles and turn up while making the album. All we had time to do was pray and be obedient to the art, because that’s the only way we could heal.”

Lamar banked his 11 Grammy nominations—a number second only to Michael Jackson’s in the award’s history—on the strength of an album that is unapologetically jazz-inflected and socially aware. In an interview with The New York Times, Lamar said he wanted to win all of them. “It’s not only a statement for myself, but it’s a statement for the culture. They’re all important because of the foundation the forefathers laid before me. Nas didn’t get a chance to be in that position. Pac. So to be acknowledged and to actually win, it’s for all of them.” On the big night, he secured five trophies: four for songs from Butterfly and one for best music video, shared with Taylor Swift, for “Bad Blood,” on which he’s featured. (He lost the album of the year award to Swift.)

Washington, Martin and Thundercat, on the other hand, have all told the press that they don’t care about the nominations. Thundercat contents himself with the oblique light that Butterfly manages to shine on jazz. “They almost put that motherfucker in the jazz category,” he says, laughing hysterically. “He got Grammys for parking, going to the vending machine—he got Grammys for having the most braids.”

Washington and Thundercat’s own work, though critically acclaimed, did not garner a single Grammy nod. It’s no surprise the staunchly traditional committee bypassed Thundercat’s The Beyond/Where the Giants Roam EP. While the Grammys have attempted to stay relevant, particularly by featuring an explosive performance by Lamar, the jazz category is woefully out of touch. With the exception of Esperanza Spalding, there hasn’t been a Grammy winner in the jazz categories under 50 years of age in decades.

What’s not as easily explained is how Washington’s solo debut, The Epic, was left out. The triple-disc album landed on nearly every 2015 best-of list. It took Washington from being an obscure player who wrote and performed on Lamar’s album to a bona fide star in the jazz world and beyond. The Epic has made jazz fans out of people who hated or ignored the genre.

The snub puts Washington in good company. “I didn’t let it upset me, but I can’t say I wasn’t surprised at not getting nominated,” he says. “So much good music has been overlooked for so long, and so many cool things have come from The Epic, that I can’t really be mad.”

Washington was sidelined after he broke his ankle during a November 2015 tour stop in Europe. That downtime gave him the opportunity to write sheaves of new music, which he hopes to record between a full slate of shows this year—including Coachella. To put this in perspective, a straight-ahead jazz musician playing the hipster-friendly festival is as rare as Michael Jackson popping up at Hot 97’s Summer Jam (which actually happened; google it).

Martin is currently working on albums for Compton rapper YG and for Lamar’s Top Dawg labelmate Schoolboy Q—not to mention Martin’s idol Herbie Hancock. He recently released his solo album Velvet Portraits, which features Snoop Dogg, Lalah Hathaway and Martin’s father, Curly, on drums.

Thundercat says he and Pittsburgh rapper Mac Miller have written several albums’ worth of material together, including straight jazz. He’s also figuring out where to place a few songs recorded with Wiz Khalifa. Thundercat’s super-group WOKE, which includes L.A. producer Flying Lotus (he of the apocalyptic 2014 album You’re Dead!) and experimental hip-hop duo Shabazz Palaces, will release more of its psychedelic disco funk this year.

“The fact that as a musician you can make music speaking from your heart that doesn’t have to be widely accepted on a commercial level—that is kind of a new sentiment,” says Washington. “I think that alone will definitely inspire the younger generation to at least try harder. They have the opportunity to go in; we had to fight our way.”

In early March, Lamar, almost without warning, released an eight-song collection of outtakes from the Butterfly sessions. The surprise album has verses from his recent television performances as well as ideas formed in the studio that had yet to be fully fleshed out. Despite being announced only hours before the release date, untitled unmastered immediately shot to the top of the iTunes and Billboard 200 charts.

Most artists would be apprehensive about opening their process to potential copycats, but these guys seem to know deep down that the alchemy behind Butterfly, as urgent as it may be, is part of something greater. Martin recalls, “When Kendrick said he was gonna put the jams out, I said, ‘You’re gonna put our secrets out? You’re gonna put the blueprint out?’ He said, ‘Yeah, man, we got a new blueprint.’ So that was that.”