Lionel Richie and Lisa Parigi (40 Years)
There is not another singer on this list that is more iconic than Lionel Richie. This man has enjoyed an unprecedented career and is widely recognized for his endless string of romantic ballads. And of course, the women love them some romantic ballads, which has enabled Mr. Richie to score many a young lady over the years, maybe none as young as his current armpiece, Lisa Parigi, a model who is a whopping 40 years his junior.