Lauryn Hill
There’s not a person who grew up in the ‘80s and ‘90s who doesn’t know who Lauryn Hill is. To this day, artists credit Lauryn for being their inspiration and the queen of R&B during its golden years. Sadly, like so many celebrities on this list, the origin of Lauryn Hill’s financial struggles is back taxes.
Between 2005 and 2007, the R&B diva reported a “climate of hostility” and “manipulation,” whatever she means by that, had taken their toll on her musical creativity. As a result, she wound up spending three months behind bars and having to pay the IRS over half a million dollars as soon as she got out.