The 10 Most Notorious Celebrity Womanizers


Charlie Sheen at the People's Choice Awards in 2007.
Our list of Hollywood's most famous male serial daters.

6. Hugh Hefner. Hef is the brains behind Playboy. There was a reality show that followed his life with three live-in girlfriends well into his 80s. Need we say more? Hugh Hefner Gets Engaged To Playmate Crystal Harris

7. Colin Farrell. From Britney Spears to Paris Hilton, Lindsay Lohan to pre-Brad Angelina, Colin Farrell has had his fair share of females. To cement his womanizer status on our list, he apparently once spent over two hours trying to seduce Dame Eileen Atkins—who happens to be 42 years his senior. She declined. One of the few to do so, it seems…


8. Desi Arnaz. Desi was one of the original Hollywood womanizers. When he was married to Lucille Ball, his excessive flirting and heavy drinking took a huge toll on their relationship. In his autobiography, A Book, he even went so far as to say he was culturally programmed to sleep with prostitutes and cheat on his wife. Interesting excuse for infidelity, isn't it?

9. Jude Law. The Brit charmer cheated on Sadie Frost with Sienna Miller. Then, he cheated on Sienna with his nanny. Next, he got a model preggers before making up and breaking up with Sienna again. We try to keep up. Jude Law & Sienna Miller: Splitsville

10. John Mayer. If you're a talented and successful Hollywood beauty, you should probably watch out. John is no doubt about to charm you… unless he already has. The soulful singer has managed to hook up with a good portion of the entertainment elite. Jennifer Aniston, Jessica Simpson, Jennifer Love Hewitt, Mandy Moore, Minka Kelly and Taylor Swift are among his conquests, and we don't exactly hear any of those gals singing his praises. In fact, it's the opposite. Swift told us all we needed to know about Mayer's ways on her track, "Dear John": "All the girls that you've run dry have tired, lifeless eyes 'cause you've burnt them out." Ouch.

Photo Credit: INF

Must-see Videos
Most Popular