It's a sad fact that most celebrity marriages wind up in divorce, so picking the worst of the worst was no easy task.
Roc-a-Fella Records co-founder Damon Dash married then up-and-coming designer Rachel Roy in 2005 while she worked at Rocawear. Four years later, Roy filed for divorce. Following the split, much hasn't been heard about the former couple, until recently. Roy received full custody of their two daughters in April 2015 and days later, Dash fired back, filing a lawsuit, accusing her of interfering with his earnings.
(Photo: Evan Agostini/Getty Images For Tribeca Film Festival)