Usher
Back in the early 2000s, R&B veteran Usher was in a relationship with TLC member, Rozonda "Chilli" Thomas. Many fans thought it was a match made in heaven. But three years later, the couple called it quits since Usher was unfaithful in the relationship. Also, according to Usher's Behind the Music on Vh1, he said once Chilli refused to marry him, the couple decided to take a break. After the breakup, Usher released his diamond-selling album, Confessions, in 2004. The set was heralded by five chart-topping singles including "Yeah," "My Boo," "Burn," "Confessions Pt II," and "Caught Up."
Usher also began a relationship with his former hairstylist, Tameka Foster, but fans were not pleased with their union. However, Usher stuck by Tameka, married her and had two children, Usher IV and Naviyd. Two years later, Usher filed for divorce and released the autobiographical single, "Papers," and released another platinum selling album, Raymond v. Raymond.