David Cassidy
In 2015, Cassidy filed for bankruptcy despite selling over 25 million tracks when he was at his peak. The '70s heartthrob worked against an addiction to drinking, which resulted in him getting numerous DUIs. It wasn't long until his wife divorced him, which pushed him completely into financial ruin in 2014. Tragically, Cassidy passed due to alcoholism issues in 2017.
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