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Lupe Fiasco – The Coolest Lyrics 16 years ago
Good call livinlikeimfromDC. He's really putting a magnifying glass of all the things that are perceived as being cool to the ghettos and people living in them moreso that still have not solved the problem of being obsessed with these material things. And this michael young guy aka "the cool" is head over heals for "The streets" (who isn't in love with him she's using him) cause he's getting all these material things he loves and he had a REAL baby with a REAL woman and ends up neglecting the both of them and once again the cycle will start over because "the cool's" father left him also.
The end of the last verse explains it

"The ones that were, fighting in class, who might not pass
Rap record pressured to laugh, at a life not fast"
The the kids who weren't smart fell the have no choice but to be hustlers because of the way rap is today and pushing for these drug dealing hustlers

"Can you feel it? [echo], that's what I got asked
Do I love her? [echo], said I don't know"
his REAL woman asking if he feels the baby in her stomach and asking if he loved her

"Streets got my heart, Game got my soul"
Self explainitory

"One time missing sunshine will never hurt your soul"
If he loses his "sunshine" his REAL girl telling her it's not gonna hurt him

"Quote: To a crying dishonored baby mama
Who's the mama to a daughter that I had fathered from afar"
Now this woman is crying and he's just disgusting on the next line

"My new lady gave me a Mercedes and a necklace
With a solid gold key (ki) like the starter of a car"
The streets being his other lady gave him some "cool" things so why would he need his baby's mother. Also lady could mean white lady as in coke. she also got him a gold key or ki as in kilo of coke

"The opener of a door or two pounds of raw"
The gold key to open a door or 2 pounds of raw drugs

"You gave me a baby, but what about lately?
Then ha-ha-ha-ha-haw'ed, right up in her face, G
There's more fish in the sea, I'm on my mission to be, be"
He now then laughs at the real woman leaving her for "the streets" because it's what's more important to be cool... he'll find another girl.

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