4. Justin Timberlake and Fergie
The two pop stars dated in 1998, back when they were friends with a whole lot of benefits.
5. Josh Groban and January Jones
American actress and model January Jones was rocking it hard with singer / songwriter Josh Groban for a time. Groban claims it was the longest relationship he has ever had.
6. Billy Corgan and Jessica Simpson
From the totally opposite music genres that both thrived on, it would be awfully tough to imagine that the two really dated. But in an interview with Howard Stern, Billy Corgan pretty much spilled the beans, saying that he “sort of kind of went out with” Jessica Simpson.
