Yes. Kanye made the list twice. On a list that is dominated by albums that were well received in the mainstream it only makes sense. College Dropout is Kanye's first release, after working heavily producing music for Jay-Z in The Blueprint, also working Beanie Sigel, Scarface, T.I., Cam'ron and Talib Kweli to name a few. After proving himself as a renowned producer, making Jay-Z's classic anthem "Izzo (H.O.V.A.)," West proved to critics that he had the ability to also spit game about more than guns and drug dealing.
The album was released in February of 2004 and fared wonderfully on the charts, producing three top ten singles and putting out two others that did well, to say the least. His first single was "Through the Wire," which talks about a car accident that Kanye was involved in, thankfully escaping death, leaving him with a broken jaw. On the track Kanye raps with his jaw wired shut, making him sound nothing like he usually would. His forth single would be his most successful, "Jesus Walks" launched on to the charts and deservingly won a Grammy for the best rap song of the year. Lyrically, the album ventures away from the then dominant street gangster rap into a more observational approach, touching up on subjects that Kanye felt were worth addressing in current affairs. Things from the government, materialism, religion and more are explored on the album. The fact that Kanye managed to create a mass fan base and following by doing something different and untraditional in mainstream rap is well worth applauding. It is also important to realize that the entire album was produced by 'Ye, relying heavily on soul and R&B samples like Chaka Khan's "Through the Fire," and also other tracks by Curtis Mayfield, Luther Vandross, Aretha Franklin and more. The albums that followed College Dropout do not follow this trend, but instead are proof of Kanye's innovative style and progression in hip-hop. All this being said, I think it is pretty obvious that Kanye deserves a spot high up on the charts, even two spots.
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