Lindsay Lohan
Reckless early adulthood full of partying and riddled with unchecked addiction forced Lohan to file for bankruptcy in 2012. She attempted to regain her lost cash by making and releasing a pop album, which flopped and actually ended up putting her further into the hole. In 2018, Lohan talked about her finances in an interview. She revealed that she had turned her life around and was worth $800,000 at the time.