Cadillac Jack - Andre Williams

On the south side of Chicago lived a guy named Jack

Whose dream it was to someday own a Cadillac

He gambled for his money, the first thing you know

Up popped Jack in a brand new El Dorado

It didn’t matter if he had no place to stay

He slept in his car at night and he drove all day

Hustling for a living, he could really shoot pool

And didn’t think it was a necessary to stay in school

A long white Cadillac was his claim to fame

And to keep up his name

(What's the dude’s name?)

Cadillac Jack

Sure was a mack

Life was good to Jack and he thought he had it made

'Til he started foolin" around with another fella’s babe

Jack had a way with women and he couldn’t understand

Why this girl refused him to stay with her man

Jack said, «Now listen baby», grabbed her by the arm

'Cause he just had to show her how good he could charm

With no word or warning came a burst of light

As Jack made his final mistake that night

Talkin' real loud, drawin' a crowd

You knew his name really made him proud

What’s the dude’s name?

(Cadillac Jack)

Sure was a mack

Now Jack was a legend on our side of town

Too bad the girl’s boyfriend shot him down

A few days later Jack was flat on his back

Gettin' his last ride in a long, long, black, black, Cadillac!

That was Cadillac Jack

Sure was a mack

(Cadillac Jack)

Sure was a mack

Cadillac Jack

Sure was a mack