Singer Toni Braxton, who had a string of chart-topping R&B hits in the 1990s including “Un-Break My Heart” and “You’re Makin’ Me High,” has filed for bankruptcy, according to Reuters. Court papers list Braxton’s assets as ranging from $1 million to $10 million and her debts ranging from $10 million to $50 million. This is Braxton’s second bankruptcy filing; her first was in 1998, following a split with her record label. Over the course of her career, Braxton has sold some 40 million records and won six Grammy awards. Her most recent release, Pulse, debuted at No. 9 on the Billboard charts last May, but sales of the album quickly flagged.