Compared to the superhero status of MCs like Big Daddy Kane and LL Cool J, De La Soul were more like the socially awkward kids in class who also happened to be the smartest folks in the room. Comprised of two MCs — Posdnuos and Trugoy — a DJ (P.A. Mase) and their mentor/producer Prince Paul, the Long Beach crew redefined hip-hop’s possibilities and sensibilities with their debut, 3 Feet High and Rising. Though they had a solid braggadoccio hit with their P-funk-powered single “Me, Myself and I” the true heart of the album and group lay more in the eclectic way in which they mined children’s records (“Three Is the Magic Number”) and Hall and Oates hits (“Say No Go”) alike for samples, created new slang around sex (“Buddy”) when they weren’t rapping about body odor (“A Little Bit of Soap”) and singlehandedly pioneered the rap album skit. Hip-hop in ’89 was already in the midst of an evolutionary leap in diversity and creativity; De La gave all that a playful nudge.

– Oliver Wang