This is the song that made me realize Biggie was far more than just the guy behind a few great singles on MTV in my youth. It took years, but Gimme The Loot launched him from a dream to the pantheon of all-time great rappers, in my view.

The beat is monstrous and the lyrics hit hard and fast, dancing in a trick-move delivery that is still mostly unmatched in the world of hip-hop. Biggie could spit rapid fire with eloquence, twisting literary turns of phrase and gutter-blast shade in the same bar, all with a flow and voice so catching and endearing, it was inevitable he’d become a megastar.

Because of the time and place I grew up, my biggest association with hip-hop was via MTV, so my biggest impressions of Biggie were the Puff Daddy features that came right before and after his death. Great songs, no doubt, but oversaturation pushed me away. It wasn’t until the end of the decade, when cruising with friends, getting high, and listening to rap for hours on repeat, that his true genius revealed itself. I was tapped in and could no longer look back. This guy was as real and perfect as Nas on his debut, or 2pac on his last album, for that matter. The skill and artistry cut through the fog of ubiquitous Puffy videos and overabundance of so-so posthumous collections, and I realized what all my friends were loving years before.

As it is, he was cut down in his prime and we’ll never know what could have happened. But this song, and the album it’s found on, Ready To Die, will always stand as a testament to the heights of artistic power that major label rap achieved in the 1990s.