TLC
At the height of their career, T-Boz, Left Eye and Chilli were the biggest-selling girl group of all-time. Their sophomore album, Crazy Sexy Cool, sold over 11 million copies and featured four top 5 pop hits. But while the album was still riding the charts, the group filed for bankruptcy. Via their deal with LaFace Records, they were only to receive 7 percent in revenue from their album sales and, after paying managers, producers, expenses, and taxes, they were only taking home about $35,000 but had amassed debts closer to $3.5 million. It took almost four years for the group to re-neegotiate a deal and rescind old production contracts that had strangled them financially.