"Around the Way Girl" (LL Cool J)

Looking back over the music career (I'm not even going to touch the TV/acting career) of James Todd Smith, a.k.a. LL Cool J, it has been pretty uneven.  Each album was a complete crapshoot: one album groundbreaking (Radio), the next kind of lame and forgettable (Bigger and Deffer).  
The key to his best work, in my opinion, was how well he gelled with the DJ/producer at the helm of each project.  If his producer was creating sick beats/finding great samples for him to rap over, then LL Cool J did his job and whaled on them like a prize fighter.  
Case in point: my favorite collaboration of his was with Marlon Williams, a.k.a. Marley Marl, on Mama Said Knock You Out (1990), an album that is filled with worthy hits and obscure classics.  Marley Marl had a way of keeping beats raw and rooted in hip-hop while also adding a pop sensibility—kind of like The Bomb Squad meets Jimmy Jam & Terry Lewis.  That technique gave a certain grit yet accessibility to songs like "Around the Way Girl," which is basically a ballad to all girls from the hood.  At a time in rap when lyrics were taking a misogynistic turn, here was an MC who told ladies they were beautiful for being street smart, independent, and confident.  It was refreshing and catchy as hell.  (Just try not singing along with The Flex on the chorus.)
Granted, he took some heat from the rap establishment, which griped that tracks like "Around the Way Girl" were "too soft," "too commercial."  But his fluid rhyming over Marley Marl's smartly-used samples of jazz/R&B artist Keni Burke's "Risin' to the Top," the Mary Jane Girls' "All Night Long," and The Honey Drippers' "Impeach the President" made the song an undeniable classic.