The British director had just begun to establish himself in the film world when he snagged one of the music world's biggest stars. When Guy Ritchie married Madonna, 10 years his senior, in 2000, some wondered if it was just a publicity stunt for his latest flick Snatch. Nope, she really was going out with him. But when the marriage hit the rocks in 2008, all eyes turned once again to the disparity between the two. Madonna's estimated fortune of $450 million was a whopping 10 times that of Ritchie's. Unexpectedly, though, Ritchie shunned all monetary gain in the rather smooth divorce proceedings, claiming his renewed bachelor status was the ultimate score.