25. Big Pun
Despite his large frame, Big Pun's fun, fast and feisty rhymes kept him light years ahead of his peers. He was also the first solo Latino rapper to go platinum. How's that for cultural impact?
Essential: Capital Punishment
24. LL Cool J
LL's longevity has never been disputed--he hasn't been able to "Live Without His Radio" since 1985--and, unlike other 80s icons, Cool J has managed to reinvent his style over the years to reflect the current hip-hop landscape.
Essential: Mama Said Knock You Out
23. Big L
Gunned down in his prime at 24 on February 15, 1999, the rest of Big L's talent followed him to the grave. But he left behind enough material to make a case as one of the most talented poets in hip-hop history.
Essential: The Big Picture
22. Masta Ace
Surrounded by Juice Crew vets like Marley Marl, MC Shan, Big Daddy Kane, Biz Markie, Roxanne Shante, and Craig G, Masta Ace was an unsung talent early on. Still, his wit, wordplay and consistency eventually earned him a spot among the greats.
Essential: Disposable Arts
21. Pharoahe Monch
Through his panoramic vision and hyper-realistic narratives, Pharoahe Monch solidified a reputation as one of hip-hop's eminent lyricists.
Essential: Internal Affairs