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Why isn't this guy considered to be up there with Pac/Nas/Biggie/Jay-Z/whatever other higher echelon of rappers/hip hop artists. He's got some amazing songs.
Too Short makes excellent fun tracks, but he's not a killer on the mic. He's from the days pre-Rakim where it was a very basic rhyme scheme, and that's exactly how he plays it. He's still a legend but he's not in that top flight of rappers. It doesn't help he's been virtually underground his entire career. Good storyteller but not anywhere near the level of Slick Rick.
To clarify, you're essentially saying he's just too simplistic with his style of rap in comparison?
Simplicity is a factor, but also because there's no deep meaning behind most of his records. All he really raps about is sex.
A lot of it boils down to this. Skill-wise, I don't think anyone has any doubts. The thing is, he pretty much wraps about nothing but bullshit.