Hip-hop lost one of its most unique elder-statesmen Tuesday morning with the passing of Pumpkinhead, known in more recent years as PH. Born Robert Diaz, Pumpkinhead’s 18-year presence in the New York hip-hop scene, as well as broader rap countercultures in general, is without peer. Very few artists from the mid-90s shared such a penchant for consistent reinvention, allowing him to remain in a state of constant relevance to the day he died. Even in death, the outspoken condolences issued by everyone from Chuck D to El-P to Mac Miller shows just how broad PH’s impact truly was.

aw man rest in peace, pumpkinhead. one of the coolest, kindest people to walk this earth.

— el-p (@therealelp) June 9, 2015

Pumpkinhead’s legacy goes back to 1997. While New York was beginning to see the rise of its underground scene through groups like the Juggaknots, Company Flow, the Arsonists, and Non Phixion, Pumpkinhead closely followed with his debut single, “Dynamic.” Along with the track signaling the start of his signature sound, “Dynamic”’s arrival was accompanied by PH’s own abilities as a one-man street team, turning street posts in all five boroughs into a sea of Pumpkinhead stickers. “Pumpkinhead’s [stickers] were some of the most prevalent,” Pumpkinhead’s contemporary, MC/producer and New York underground historian, Uncommon NASA says. “They were half-super aggressive, supposed to be half-Pumpkinhead and half-human.”

Along with the street-visibility, “Dynamic” found its way into rotation on progressive underground taste-making New York radio show Stretch Armstrong and Bobbito. Through the turn of the millennium, PH continued to release championed underground singles as a solo artist as well as collaborations with groups like Brooklyn Academy and Skeme Team, who released the essential 1999 single “Con Artists.” Not merely content with just putting out music, Pumpkinhead also became one of the most celebrated contenders of the freestyle battle scene. Gaining nationwide press for his showing in the Blaze Battles, he also inadvertently became the gateway drug for a whole generation of rap battle fans as MP3s of his showdowns with MCs like Tonedeff and Breez Evahflowin became some of the most shared audio battles on file-sharing services like Napster, Limewire, and Kazaa.

But as the next generation of New York hip-hop came to the forefront and weekly events like End of the Weak (EOW) became the new hotbed for New York hip-hop, Pumpkinhead kept with the times by being a genuinely active and encouraging figure. Already a five-year veteran, Pumpkinhead notoriously didn’t let his years of success divide him from where hip-hop was going and became something of an older brother for the new torch-bearers. His experience didn’t quell his hunger as he still competed in EOW’s world famous rap-skill obstacle course, the MC Challenge, which he won on four occasions. This next wave of success kept Pumpkinhead fresh in the underground-turned-indieground scene, landing him memorable cameos on underground classics from Immortal Technique, Pack FM, Jean Grae, and Philaflava’s A League of Their Own Volume 2 compilation. Pumpkinhead capped off this era of his career with his critically acclaimed 2005 album, Orange Moon Over Brooklyn. The career-launching point for producer Marco Polo, Orange Moon Over Brooklyn’s combination of high-concept songs and syllable-stacking made for a something-for-everybody affair.

Even after so much success with his recorded music, Pumpkinhead saw the emerging new battle scene of the late-aughts as a chance to step back into the ring and reinvent himself once again for a new generation of fans. Rechristening himself PH, he took on the emerging Grind Time promotion’s flagship battler, Dizaster, and won convincingly. Not merely content with his appearance being a one-time-only nostalgia showcase, PH stayed active, facing the top talent this new generation had to offer including Dumbfounded, the Saurus, and Arcane. While he fell just short of winning battle league King of the Dot’s championship title in 2012, he battled as recently as this year against heavy hitters like Madness and, in his final battle on May 31, Yung Casper.

Rap battles would be the only time one would hear PH utter an unkind word about an MC. In his entire nearly two-decade run, PH was a welcoming presence who would remember and offer encouraging direction to every MC he would meet. “I had maybe three interactions with him,” remembers Jus Daze, an MC who started as a fan and became a close friend, “I was 500 pounds, I went away for a while, came back having lost 250 pounds, and he remembered me. PH was the guy who, when he came up and told me ‘you’re nice,’ I felt I was doing something right.”

PH was scheduled to return to End of the Weak to compete for his fifth MC Challenge title this Sunday. The freestyle event’s organizer, Baxter Wordsworth, considered booking PH for the freestyle competition to be a no-brainer as “he always maintained a sense of royalty in the underground community. When we talk about him with younger MCs, there’s a sense of reverence. Putting his name on the flyer garnered so much attention for the MC Challenge.” It’s another example of how PH’s cross-generational cross-sub-genre impact is unparalleled in (especially New York’s) underground hip-hop. From pressing his own vinyl in the D.I.Y. era to releasing a critically acclaimed album in the indie-ground explosion to being a major player during battling’s biggest moment, it's not a surprise to see his untimely death mourned by so many for so many different things. 

The only thing PH never did was divulge why he called himself Pumpkinhead. “To this day,” Jus Daze tells us, “I remember asking him ‘Yo, P, what if somebody in a battle says something like ‘Why they call you Pumpkinhead?’ He said, ‘Nope, they’ll never find out.’”

The cause of PH’s death has yet to be made public. He’s survived by his wife and two children, with a third on the way. A memorial fund has been set up for PH’s family here. He was 39.

Chaz Kangas is a writer living in New York. Follow him @Chazraps.