Rap is a youngin’s hustle. Superstars are launched in their teens, legends are minted in their twenties, and by age 30, odds are, you’re broke. Scrounging for a supplemental income. Shilling for shampoo brands. Slumming the clumsiest of Eastern Hemisphere pop-rap. All to pay back taxes, legal fees, and the mortgages of however many mansions that you won't own for much longer.

Unfortunately, rappers have a history of letting their troubled finances make for atrocious art, just to get by. Here we've compiled nine egregious instances of rappers on some pay-their-bills shit. This includes ill-advised rap collaboration, cynical endorsement deals, and consumer fraud. In a few sad cases, the desperation is understandable and, thankfully, forgivable—really, Rakim can do no wrong. DMX is long beyond salvation, though. And Juelz? Boy, you know you wrong.

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