14. Hugh Hefner

Hugh Hefner has by far the longest dating track record of all the men on the list, maybe even combined.

Granted, he’s twice the age than some of the men we’ve covered, meaning he simply had more time to work on the said record.

Back in the early days of Playboy magazine, (and let’s not forget he founded the magazine in 1953) Hugh Hefner was a decent-looking, 27-year-old psychologist, working as a copywriter for Esquire.

The fact that he’s a successful publisher and owner of an adult magazine doesn’t make him as ugly as his escapades with hundreds and maybe even thousands of desperate 20-year-olds who would do anything for their 15 minutes of fame.

To make matters worse, most of those girls’ mothers weren’t even born in 1953, making him one of the most appalling womanizers of all times.