Like many other lines in this song, Webby takes Asher Roth’s laid back frat-boy lines and takes them to the extremes. Asher said when your wasted, time won’t be wasted, but Chris says he’s always wasted so time isn’t wasted.

He smokes so much you would think it’s actually legal for him to do it.

Most rappers claim they pour their feelings onto their record, but few do it as well as Lupe.

In Lupe’s opinion everything that isn’t evil has at least some good in it, so it has to be good or evil.

Bass can refer to the bass of a drum beat. A car with rims probably has a loud stereo, which emphasizes the bass in a song. It is also a homophone to base, a drug high in amphetamines. Some people get high on music, some people get high on drugs, it depends how you live your life.

Henry Horner is a public housing development in Chicago’s westside.

Lupe’s sister, who also does the intro to Lupe Fiasco’s The Cool gives a spoken word intro.

Both are common liquor stores in Chicago.

Refers to Gwendolyn Brooks' “We Real Cool” poem. The original was

We sing, sin, thin gin

Lupe is also interested in what kids consider “cool”, as evidenced as his second album.

J&J’s is a restaurant commonly found in the Southside. It sells fried fish and chicken.