| On the south side of Chicago lived a guy named Jack
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| Whose dream it was to someday own a Cadillac
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| He gambled for his money, the first thing you know
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| Up popped Jack in a brand new El Dorado
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| It didn’t matter if he had no place to stay
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| He slept in his car at night and he drove all day
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| Hustling for a living, he could really shoot pool
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| And didn’t think it was a necessary to stay in school
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| A long white Cadillac was his claim to fame
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| And to keep up his name
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| (What's the dude’s name?)
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| Cadillac Jack
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| Sure was a mack
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| Life was good to Jack and he thought he had it made
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| 'Til he started foolin" around with another fella’s babe
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| Jack had a way with women and he couldn’t understand
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| Why this girl refused him to stay with her man
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| Jack said, «Now listen baby», grabbed her by the arm
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| 'Cause he just had to show her how good he could charm
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| With no word or warning came a burst of light
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| As Jack made his final mistake that night
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| Talkin' real loud, drawin' a crowd
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| You knew his name really made him proud
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| What’s the dude’s name?
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| (Cadillac Jack)
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| Sure was a mack
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| Now Jack was a legend on our side of town
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| Too bad the girl’s boyfriend shot him down
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| A few days later Jack was flat on his back
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| Gettin' his last ride in a long, long, black, black, Cadillac!
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| That was Cadillac Jack
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| Sure was a mack
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| (Cadillac Jack)
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| Sure was a mack
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| Cadillac Jack
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| Sure was a mack |