Marvin Gaye
In the mid-70’s, Marvin Gaye had an impressive fortune to his name, thanks to almost 70 hit songs that he had written and performed. Even though he was super talented, he wasn’t very good at tracking his spending habits and ended up living beyond his means, and racked up a huge debt.
This was all on the down low, until he was ordered to court to record a new album and give all the royalties to his ex-wife Anna Gordy as alimony for their divorce in 1977. That album ended up with dismal sales and he ended up owing what the court and label thought the royalties should have been, and not what they were.
Ironically enough, they remained friends.