On a bare patch of Manhattan's Fourth Street, between Avenues C and D in Alphabet City, the rapper Kool Moe Dee sits behind the wheel of a Jeep Wrangler. Under one of its tires lies a red kangol hat, flattened into the dirt. The photograph, taken across from the San Isidoro y San Leandro Western Orthodox Catholic Church of the Hispanic Mozarabic Rite, became the cover of How Ya Like Me Now, his second solo studio album, released on November 3, 1987 on Jive Records.
The kangol hat and the feud
The crushed hat was not a random prop. Kool Moe Dee, a former member of the pioneering group Treacherous Three, aimed the gesture squarely at LL Cool J, a younger rapper he accused of stealing his style. The feud had begun when Kool Moe Dee claimed LL Cool J copied his rap technique, and it deepened when LL Cool J called himself the new grandmaster of rap without acknowledging predecessors like Melle Mel and Grandmaster Caz. For Kool Moe Dee, that was an insult to the culture's founders.
The album turned that resentment into a commercial weapon. Across eleven tracks, Kool Moe Dee blended hip-hop with the emerging new jack swing sound, a style built on electronic percussion and sharp, syncopated beats. He produced the record himself alongside Teddy Riley, Bryan "Chuck" New, LaVaba Mallison and Pete Q. Harris, the same team behind his self-titled 1986 debut. But this time the stakes were higher: he was no longer just a veteran rapper, he was a man defending his legacy in public.
Singles and chart performance
The title track became the centerpiece of the attack. It climbed to 22 on the US Billboard Hot R&B/Hip-Hop Songs chart and crossed over to the UK Singles Chart at 86. The second single, "Wild Wild West," did even better, hitting 62 on the Billboard Hot 100 and rising to 4 on the Hot R&B/Hip-Hop Songs list. All three singles from the album, including "No Respect," received music videos, which kept Kool Moe Dee's face and his challenge in heavy rotation.
The album itself became a slow-burning hit. It reached 35 on the Billboard 200 and stayed on that chart for 50 weeks, while climbing to 4 on the Top R&B/Hip-Hop Albums ranking. On April 14, 1988, the Recording Industry Association of America certified it gold, and on November 14, 1988, it went platinum. That certification meant sales of over one million copies in the United States. How Ya Like Me Now remains Kool Moe Dee's best-selling album.
Critical reception and production
Critics heard something unusual in the record. The New Musical Express gave it an 8 out of 10, and Robert Christgau awarded it an A−, describing the sound as a "knocked-out swing" driven by electronic percussion. Christgau pointed to the trick rhymes, shifting line lengths, filters, double-tracked vocals and sung refrains as evidence of a rapper pushing beyond standard battle-rap formulas. The album was not just a diss record; it was a production showcase.
The cover photograph tied the music to a real place. Kool Moe Dee mentioned details of the Alphabet City neighborhood in the album's lyrics, grounding his boasts in the streets where the Jeep-and-kangol image was shot. The empty lot across from the church became a stage for hip-hop's most literal act of disrespect: running over a competitor's signature hat. The feud with LL Cool J would continue into the mid-1990s, with both rappers eventually declaring themselves the winner, but the cover of How Ya Like Me Now froze the conflict at its sharpest moment.
The empty lot across from the church became a stage for hip-hop's most literal act of disrespect: running over a competitor's signature hat.
The album's title question was answered by the marketplace. The album earned platinum status and secured a place in later retrospectives. In 2017, Consequence of Sound ranked it among the best albums of 1987, and Complex placed it among the greatest rap albums of the 1980s. Kool Moe Dee had turned a grudge into his finest work.