So my top 50 MCs list is already screwed up. I was going to make this entry about Posdnuos but then realized how many of my favorite De La lines were Trugoy’s (not to mention “Itzsoweezee” which gets Dave a spot on here all by itself (and if you didn’t know that already then the only Italians you know are icees)). Both guys belong on the list because their styles are quirky, inimitable, and essential – you often have to work through coded slang to find the life lessons. But that’s what makes for such rewarding and relistenable music.

De La Soul started as semi-hippies in the late 80s before becoming culture critics and pissing off 2Pac in the mid 90s, releasing four straight classics in the process. It’s a phenomenal run that bridges multiple eras, from the sample heavy day glo goofiness of 3 Feet High And Rising to Stakes Is High, which featured early appearances of Common, Mos Def, and J Dilla. In between we got 1993’s Buhloone Mindstate, which will forever be in my personal top 10 albums in any genre. It is peak De La, with Prince Paul’s detailed jazzy production matched with their most abstract, impenetrable lyrics. And the ‘pop-music-as-nitrous-balloon’ metaphor is perfect.

From the start Posdnuos and Trugoy rejected familiar rap tropes in favor of weirdness and social commentary. But here’s the thing – sometimes ‘conscious rap’ feels like a scolding parent lecturing and hating on everyone else in a repetitive cycle, like a late 90s Rawkus rapper chasing his own tail. De La were never conscious rappers, as their rejection of the drug and thug elements just opened up a wider palette for the genre. They offer a quirky and clever perspective that also doesn’t take any bullshit.

Moralizers but not followers, De La didn’t just comment on the culture but helped shape it. “Potholes In My Lawn” addressed biters years before Wu Tang, while Stakes Is High included pointed attacks on the Wu, 2Pac, Puffy, and Biggie at their own peaks. Pac responded memorably on his war mode Makaveli album, but I’m sure he’d have been collaborating with De La if he’d lived. And in hindsight, De La were on point in their criticisms. “I got questions about your life if you’re so ready to die” refers to Biggie’s album but addresses a more significant cultural problem.

“If I wasn’t making a song I wouldn’t be a thug selling drugs/But a man with a plan/And if I was a rug cleaner betcha Pos’d have the cleanest rugs I am…”

By their second and third albums De La Soul were commenting on the fickle nature of the music industry. Among other things – child abuse (“Millie Pulled A Pistol On Santa”), cultural identity (“Patti Dooke,” “I Am I Be”), and customer service at Burger King (“Bitties In The BK Lounge.”) But their fourth album Stakes Is High is the most potent, emerging from the bohemian bubble to address the changing rap culture. The term “stakes is high” was a prescient warning; within a year 2Pac and Biggie would be dead. Again here’s De La with the alternative, introducing the first of several collaborations with J Dilla and songs with more mature relationship advice and personal reflection.

Post Stakes De La is spottier, as their cultural commentary occasionally comes off as cranky. They had a triple album planned that was broken up by the record label; the separate albums include some classics (with Redman on “Oooh,” the Christmastime McCartney sample (and Greg Nice flow) on “Simply“) but more filler than ever before. 2004’s The Grind Date and 2016’s crowdfunded …and the Anonymous Nobody are better but not as urgent as the classic work. The production on The Grind Date is stellar courtesy of Dilla, 9th Wonder, and Madlib, but the song “Much More” is emblematic of the lyrical problem – it’s basically about how De La are more serious MCs than the rest of the field. Fine, but so what? It’s like a comedian telling a story about how funny he is.

Though their debut 3 Feet High And Rising is their most critically praised album, I would hesitate to recommend it. I not only prefer but I love Buhloone Mindstate and Stakes Is High like family members. Buhloone is Prince Paul’s production masterpiece, an insular concept album about the hip hop industry in the early 90s; Stakes is the first break in a new wave of soulful indie rap that birthed Mos Def and J Dilla (and by extension Kanye West? I’d say so.) And yes they pissed off Pac while he was in Makaveli mode.