No. 27: CL Smooth

One of the more unheralded rappers ever, Corey "CL Smooth" Penn may not be considered an all-time great by casual fans, but his peers disagree. During hip-hop's heyday in the early 1990s, CL was as respected a figure as anyone, and for good reason.

Though his time in the limelight was shorter than many on this list, CL Smooth merits being ranked this high for one simple reason — he has the distinction of rhyming on The Best Hip-Hop Song Ever Made.

(And no, that title is not up for debate.)

Use your condom, take sips of the brew...

"T.R.O.Y." was the most perfectly constructed song in the genre's history — Pete Rock's horn-heavy track provides the ideal backdrop for CL's ummm...smooth verses as he looks back at life with his family and friends. The rhyme schemes aren't the most complex, but the flow is uniquely his, and the way everything blends together with the beat can still give true hip-hop heads the chills nearly 20 years later.

Sadly, we didn't hear nearly enough from Pete Rock & CL Smooth as a duo — they split up after just two albums, though they have gotten together for various tracks since and even toured together in late 2010. Even sadder still, CL has done very little recording without his former partner, not releasing a solo LP until 2006, more than a decade after his final album with Pete.

During his apex, though, CL was all over the place, doing collaborations with a list of hip-hop heavyweights that included Heavy D and Run-DMC. "T.R.O.Y." even inspired the remix of "Reminisce" by Mary J. Blige, a track that featured Pete Rock & CL together.

If you weren't into hip-hop in 1992 and 1993, there's a good chance you don't even know who CL Smooth is. But his sound helped define the genre's best years, and he's probably had an influence on a few of your all-time favorites.

For that reason, he's one of mine.