13. Madonna and Jesus Luz (28 years)/Madonna and Brahim Zaibat (28 years)
Madonna has been the cougar queen that can’t seem to get her hand off young men. She first dated Brazilian Model Jesus Luz, who was 28 years younger than her, which caught a lot of attention. The couple only lasted an year, and you could probably figure out why. She didn’t stop. She then dated 24-year old dancer Brahim Zaibat, who is also 28 years younger than her.