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King T.I.
In the videos to his Chronic singles (and in the songs themselves) Dr. Dre's 1964 Impala has been fitted with hydraulic lifts which raise up and down. The girl's ass is being compared to this phenomenon.
Keep a prostitute working the streets as you were her pimp and keep a cigar (Swisher Sweet is a brand of cigar) full of Marijuana instead of tobacco. Pine is a slang term for marijuana because they are both green
Most likely a 4-door sedan from the 70's 80's ish, maybe convertable.
Playing rapper Too Short's music at an appreciative volume, out of a Red Candy Apple color painted vehicle (most likely a 4-door sedan from the '70s/'80s-ish, maybe convertible).