20. Madonna
If there’s anything that we know about Madonna, it’s that the Queen of Pop has always been breaking some taboos. After more than 30 years in the industry, she claimed that she had the right to do what she wanted, with whom she wanted. In her case, breaking the rules means making a habit of dating men who are significantly younger than her and not being the least concerned about other people’s opinion.
Here’s what she told The New York Daily News about her relationships with younger guys:
“It’s just what happens. Most men my age are married with children. They’re not dateable. I’m a very adventurous person and I also have a crazy life. I’m a single mother. I have four children. I mean, you have to be pretty open-minded and adventurous to want to step into my world. People who are older, and more set in their ways, are probably not as adventurous as someone younger.”
Her ex-husband, Guy Ritchie, was 10 years her junior, and she’s had a string of much younger boyfriends ever since, including dancer Brahim Zaibat, Jesus Luz and Timor Steffens, all of them half her juniors.