During the ’90s, this Grammy-winning artist generated $170 million from the sales of her first two albums. Yet, two years after the 1996 release of Secrets, she filed for bankruptcy.

The star admitted to an addiction to spending money, but the real problem was that her record label at the time (the now-defunct LaFace Records) was giving her less than 35 cents per album sold.

She ended up suing to terminate her contract.

The tough times weren’t over yet. Braxton self-financed a Las Vegas residency to avoid more financial troubles, but the plan backfired. She was diagnosed with a heart condition and lupus, leaving her unable to perform..

As a result, she didn’t earn enough to pay all the vendors. Braxton filed for bankruptcy a second time in 2010.

Still, her popularity and work ethic have endured. She continues to perform regularly and her net worth sits at$10 million.