No. 16: Kool G Rap

Part of the reason I couldn't put Big L any higher than 17 is the fact that it would've been wrong to rank him ahead of the rapper whose career he most likely would have wound up emulating.

Nathaniel Wilson, better known as Kool G Rap, was everything that Big L probably could have been — an incredibly gifted lyricist with a flair for making real hip-hop music, but someone who got far less time in the limelight than his music merited.

Takin' over the (Gary) Carter.

Kool G started out as a tag-team act with DJ Polo in the late 1980s, making a name with the single "It's A Demo." After joining up with the Juice Crew, Kool G blew up thanks to a verse on Marley Marl's "The Symphony," and he subsequently made three solid albums with DJ Polo before the two parted ways in 1993.

Anyone who was slow to get on the Kool G Rap & DJ Polo bandwagon for whatever reason (and I'm embarrassed to admit that I was) had to be fully on board after his first solo LP, 4,5,6, dropped in late 1995. The single "Fast Life," a back-and-forth with Nas, remains one of my favorite tracks of all time, and Kool G delivers a rapid-fire lesson in breath control on the first verse.

Most rappers would have needed multiple punch-ins to spit it. I practiced my own delivery by practicing it. Nas — who is ranked very, very high on this list — gets outshined on this one in a big way despite delivering an outstanding performance himself. It's a fucking awesome performance.

Kool G has remained prolific ever since, putting out a handful of solo albums and doing collaborations with fellow top-50 emcees such as Heavy D, Fat Joe, Big L, Chino XL, Canibus and Ras Kass, among many others. Now in his mid-40s, he remains one of the most respected figures in hip-hop.

My only real beef with Kool G is that he maintained a career-long obsession with the mafioso/organized crime lifestyle — and while it worked on songs like "Fast Life," it became overkill'ish when done over and over. (We needed more "Talk Like Sex," yo!)

Had there been more diversity, he might've become a top-10 emcee for me. The whole package was there — lyricism, flow, delivery, rhyme structure, you name it — but Kool G falls just short of being in that upper-uppermost tier.

Ain't no shame in being here, though.