27. Memphis Bleek
From: Brookyln, NY
Signature Song: Memphis Bleek f/ Jay-Z, Missy Elliott & Twista "Is That Your Chick?" (2000)
He couldn't have foreseen it at the time, but starting his career on a Jay-Z album was, in some ways, a seal of fate for Memphis Bleek. Of course, Bleek's loyalty to Hov has earned him lifetime millionaire status, but it's also the reason why he's totally dismissed as a rapper and seen as the GOAT weedcarrier.
At the turn of the century, he showed promise with solo hits "Do My...," "My Mind Right," and "Is That Your Chick?"-at the same time, Jay's career was reaching unprecedented heights. As a result, Bleek's efforts were overlooked. Since then, he's just been tagging along for the ride. The standout record on his last album, 534, was a Jay-Z song, "Dear Summer."