R.I.P. Pumpkinhead: Five Best Tracks From the Underground Rap Legend

This week the hip-hop world was saddened to learn of the passing of one of its most prevalent cornerstones. Pumpkinhead, known in his later years as PH, was an MC who emerged near the very beginning of the New York underground movement of the mid-90s and remained an important player transcending generations and impacting and influences every MC who made a name in the five boroughs in his wake. From the Lyricist Lounge to battles to everywhere in between, Pumpkinhead created a longstanding legacy for himself that few can compare with. On the off-chance there's some listeners not familiar with his work or just looking to relive some of his finest moments, we at the Weekly have assembled five essential Pumpkinhead clips.

Fans looking to donate to Pumpkinhead's family's memorial fund can do so here.


Pumpkinhead – “Rock On” 2005
The first single off of his magnum opus Orange Moon Over Brooklyn, Pumpkinhead's “Rock On” became something of a mid-career manifesto. It's one thing to profess your love of MCing when you've just started and the world of hip-hop is entirely fresh and new to you, it's another when you're a vet almost a decade into your career and you're still just as hungry as ever. More than just a song about rapping for rap's sake, “Rock On” is career-retrospective rap at its finest, giving a surface level of PH's accomplishments, and then giving a deeper glimpse into the psyche of his personality.

Pumpkinhead – “Dynamic (Remix) (featuring the Makin' Records Family: The Bad Seed, CES, DCQ, Meat Pie, Ocean, Pokaface, What What” 1998
But years before the New York underground scene was even putting out albums, it was a world based on 12″ singles. Pumpkinhead's 1997 debut “Dynamic” was an instant classic, but then the remix that came out as the b-side to his follow-up “Wack MCs” really took him to the next level. PH had a penchant for posse cuts over the course of his career, retroactively allowing for nice time capsules of the different styles in New York at the time, with PH himself often rhyming second. The “Dynamic” remix, which was produced by the original song's producer Run Run Shaw, later gained even bigger exposure as part of DJ Rhettmatic's mix with the World Famous Beat Junkies.

Skeme Team – “Con Artists” 1999
Pumpkinhead, despite a strong battle legacy, always managed to play well with others. A great collaborator, he always knew how to play to his fellow MCs strengths without diminishing his own lane. Along with groups like Brooklyn Academy and #TeamHomi, Pumpkinhead was part of Skeme Team, a trio who released the absolute classic 1999 single “Con Artists.” An underground essential, it's where tradition and innovation meet.

Immortal Technique – “Peruvian Cocaine (featuring Pumpkinhead, Diabolik, Tonedeff, Loucipher, Poison Pen and C-Rayz Walz” 2003
Pumpkinhead's most heard verse may have come on Immortal Technique's 2003 Revolutionary Vol. 2 album. One of the highest concept posse cuts ever recorded, “Peruvian Cocaine” is a step-by-step diagram of how cocaine makes it way from Peru to America with each MC using their distinct style to play a different part along the way. Once again, PH is the second voice we here, setting the vibe off perfectly.

PH (Pumpkinhead) vs. Dizaster 2009
While not a song, no anthology of Pumpkinhead's career would be complete without mention of his epic battle career. With victories going back to the VHS tape-trading era, Pumpkinhead's voice was often the first heard whenever a curious young hip-hop fan would type “rap battle” into Napster. A champion in the freestyle era, fans were shocked when PH stepped into the emerging street format battle arena and first set-sights on the then-flagship battler Dizaster. What shocked them further was not just PH holding his own, but winning convincingly by unanimous judges' decision. The began the next wave of his battle career and introduced him to an entirely new generation of fans.

See also:
The Top 10 Rappers in OC
10 More of OC's Best Rappers
Top Five Female Emcees in OC

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2 Replies to “R.I.P. Pumpkinhead: Five Best Tracks From the Underground Rap Legend”

  1. Dope summary and the most accurate call on Orange Moon been his OM. Shoutvout to MP on the beats. RIP Robert Diaz aka Pumpkinhead

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