DMX

DMX, whose real name is Earl Simmons, rose to prominence when he dropped his debut album, It’s Dark and Hell is Hot, in 1998. The LP earned critical acclaim and also turned out to be commercially successful, selling more than 250,000 copies in just its first week of release. He released his best-selling album in 1999… Then, there is X, which includes the hit single Party Up (Up in Here).

Since its debut, DMX has released 7 studio albums. However, despite conquering the rap scene of the 1990s, the 49-year-old star still found himself in deep debt. He was even sentenced to spend six months of jail time after failing to pay his child support worth $400,000. He was once again arrested after trying to hide millions of dollars of his income from the IRS. DMX ended up with a $1.7-million bill of unpaid taxes. Sadly, his lawyer couldn’t do anything to help DMX avoid being imprisoned.