Kool Keith picks his favourite rap song of all time

Kool Keith was a key figure in hip-hop’s pioneering era. As a founding member of the Bronx collective Ultramagnetic MCs, the emcee and record producer took epic risks with sampling and pushed the creative boundaries, making the group one of the most unique of its time.

Despite his beginnings as a member of the hard-hitting New York Ultramagnetic MCs, Kool Keith, with a quirky aesthetic, ventured into the world of releasing music as a solo act in the 1990s, and with this emerged his haunting alter-ego, Dr Octagon.

Kool Keith’s 1996 debut album, as a solo act, Dr. Octagonecologyst, gave fans an abstract, intriguing take on hip-hop. Featuring short monologues, skits, and all delivered in a conversational style of lyricism, the 19-track album turned the heads of critics and received praise for being so refreshingly unconventional.

Akin to acts such as Outkast, who were releasing projects like Aquemini, Kool Keith as Dr Octagon did as much as he could to separate himself lyrically and sonically from the rest of hip-hop, which, during this period, was hooked on G-Funk and the commercial hits from Bad Boy Entertainment.

With a clear horror theme to his alter-ego, Kool Keith as Dr Octagon created a cult hit, but with his later music, like some other artists, would push the creative boundaries in shocking ways. Keith’s sophomore project, Sex Style, was polarising, and it took many back with its lyrics and irked critics. However, Kool Keith’s third project, First Come First Served, saw him return to the gritty, darker themes explored in his debut.

His output is evidence of his personal love for phishing the boundaries and the unconventional. As such, when Pitchfork sat down with the legend to find out about his favourite hip-hop track of all time, the lyricist named an act renowned for being enjoyably different—E-40.

Insisting that his favourite song of all time is E-40’s ‘Captain Save A Hoe’ from his classic 1994 EP The Mail Man. opening up about his love for it, Keith explained, “I first heard this song on the radio in LA, and I liked how it was laid-back and mixed the Oakland and LA vibes together. Anytime I heard the chorus, I would sing it.”

Explaining how he loved the difference, Keith continued, “E-40 is so naturally funny and clever. He’s a break from the average rapper. So many do street talk the same, but E has so many rhythmic tricks and vocal acrobatics. He always comes up with the flyest spin on the usual. He’s kind of like myself: You can’t duplicate his songs.”

The Ultramagnetic MCs founder expressed that he loved E-40’s pimp style, concluding, “This is a pimp song but not in a bad way—straight entertaining instead of downgrading. Even the beat is so original. It makes you want to go to Guitar Center and get one of those keyboards that they used back in the day to make those big, plump sounds. It’s soulful, music for a day riding around in Oakland, hitting a bar, and hanging with people who are real.”