Talk Dirty: He probably spent the most money ever on 976 and 1-900 numbers.

This singer was A+ for quite a length of time. He also acted and did a lot of other things that kept him in front of your eyeballs (bad Blepharoplasty) for decades. He was married quite a few times. Many of those marriages ended because of his cheating. They would grow tired of it or he would find someone to replace the previous wife. With his level of fame, he obviously had groupies and would hook up with them, but that wasn't his favorite thing to do.