In what may be the most depressing fail on our list, Lauryn Hill faces up to three years in jail for tax evasion. Earlier this month Ms. Hill pleaded guilty on three counts of evading taxes on $1.8 million of earnings between 2005 and 2007.

She took to Tumblr in June to address the situation, claiming that her "potential to work" was in danger. "There were no exotic trips, no fleet of cars, just an all out war for safety, integrity, wholeness and health, without mistreatment, denial, and/or exploitation," she wrote.

It would be a sad situation to see one of the most legendary and respected artists of our time head to prison—especially with six young children at home. Sorry Lauryn, but this is a fail on your part. Everyone has to pay their taxes, even if they were miseducated.