21. The Notorious B.I.G. f/ Bone-Thugs-N-Harmony "Notorious Thugs" (1997)
Producer: Steven "Stevie J" Jordan, Sean "Puffy" Combs Album: Life After Death Label: Bad Boy
To kick off disc two of his Life After Death masterpiece, Big took it to the crossroads of America for some Midwest bounce. "Notorious Thugs" stands as a testament to just how popular Bone Thugs-N-Harmony were in that era, as they were the only group to have worked with Biggie, Pac, Pun, and Eazy-E before those rappers' untimely deaths.
High off weed and lots of gin, Big out-rapped and out-harmonized Cleveland's Bone Thugs, taking their double-time flow and upping the ante. Seamlessly integrating himself into the track, Chris Wallace sounded like the sixth member of the Ruthless collective. Big's words were clearer, crisper, and easier to understand than those of his Mo Thug counterparts—and exhibited amazing breath control for such a big boy (pun intended).
Big even nonchalantly—albeit briefly—addressed his so-called beef with you-know-who, which proved rather unsettling because by the time we heard the track, both artists were gone. After "Notorious Thugs," countless other rappers would try their hand at their sound, but none did it quite like B.I.G.