Via Roots Manuva, and at least ten years late, I just discovered Chali 2na. I heard his name before I read it. This is important.
Ok, so aside from the pitiful middle-class objection to the number-letters (especially because I say "tyoona"), what seemed to me to be odd about his name was the 'Chali'. I panicked a little bit when I didn't see the 'r'. To me, it's essential - it makes the 'a' long like 'ma' instead of short like 'mad'. Spelling it that way, instead of being cool and phonetic, to me, takes it further away from how the word sounds. All it does is lengthen the vowel, right?
Well, that's because I'm English, and non-rhotic. If I was American, Scottish, Irish, from the West Country, I would actually say the 'r'. Well, if I was White and American I probably would. If I was an AAVE speaker I probably wouldn't.
So to us contented cheese-on-toast munchers, his rhymes on '-or' and '-ear' sound normal. To your average White Yankee, it sounds like a missing letter - like how many Britons would consider the glottal stop a "dropped t". You see this in American transcriptions of Black speech - "'Mo' Money Mo' Problems" and the nasty little bit of Jim Crow "Massa'". But, as with the first, it's often AAVE speakers writing their own speech. Non-rhotic spelling is an assertion of identity, if maybe a problematic one.
Now we start to see Chali's thinking. The 'r' is as superfluous to him as it is to me, but it's not to the standard, largely White English he wants to distinguish his speech from. Just look at the distinction that can be drawn between the n-word with '-er' and with '-a'. Rhotic abuse said by Whites, non-rhotic solidarity from other African-Americans. But sat here dreaming of living in a place with nice weather, the difference has usually been lost to me.