No. 25: Slick Rick

Once upon a time, Richard Walters was regarded by some as one of the top 3 to 5 emcees ever, and the greatest storyteller in hip-hop history. Over the years, both of those distinctions have slipped from his grasp — mostly because he was surpassed by a generation of rappers who grew up trying to emulate him.

The man who did it first still has to get some of the credit.

Born in London but transplanted to New York 12 years later, Slick Rick first came up as part of the Kangol Crew with Dana Dane, who had a similar style (but a fake British accent and, thus, a less successful career). He then linked up with Doug E. Fresh & The Get Fresh Crew, becoming an instant legend for his performances on "La Di Da Di" and "The Show," two old-school staples from the mid-1980s.

No longer too young for you, bitch.

Capitalizing on his notoriety, Rick dropped his solo debut, The Great Adventures Of Slick Rick, in 1988. The album still ranks as a classic, thanks largely to storytelling gems such as "Children's Story" and "Mona Lisa." There are also the dueling love songs "Teenage Love" and "Treat Her Like A Prostitute," offering the same mixed message on women that hip-hop has been delivering ever since.

In 1990, Walters went to jail for attempted murder and assault, languishing behind bars for three additional years due to struggles with the INS. By the time he was freed in 1995, Rick had somehow dropped two more albums, The Ruler's Back and Behind Bars, neither of which came close to reaching the heights of his first LP. By the time his final album, The Art Of Storytelling, similarly flopped in 1999, it had become clear that going to jail effectively killed Slick Rick's career.

So why is he in the top half of this countdown, ahead of rappers with far more distinguished discographies? Because many of them might not have even started rhyming had they not heard Slick Rick first. Rappers such as Snoop Dogg and Jay-Z have done covers of his songs, and others interpolated his work within their songs (like the hook from Biggie's "Hypnotize" or Ludacris' entire verse on the Nas track "Virgo").

Numerous rappers sound alike, and many styles have been bitten. But there will never, ever be another Slick Rick.

(Because if Dana Dane couldn't quite pull it off, you can be damn sure nobody else is going to.)