3 & 4. Jaimee Grubbs and Joslyn James
It's kind of a toss-up here for which of Tiger Woods's women is the most reprehensible. Jaimee had appeared on VH1's Tool Academy, which is the mark of a superior intellect, but Joslyn is a sharp businesswoman, as evidenced by her decision to put all of Tiger's XXX text messages on her website. You know what? We're playing pin-the-tail-on-the-hoochie when it comes to Tiger.
5. Ashley Dupré
Remember former New York governor Eliot Spitzer? Remember how he had a lovely and accomplished wife, beautiful children, and was doing great things to clean up New York government? Remember how it turned out he liked to go to D.C. and keep his socks on while having unprotected sex with hookers? Yeah, Ashley Dupré was one of those hookers, and she made no secret of her wish to turn hooking-with-famous-dudes into a singing career. Yeah. Good luck with that, Ashley. Eliot Spitzer Talks About The Exultation Of Love
Alexsandra is the lady who just had a baby with Beyoncé's father, Mathew Knowles, even though he's been married to Beyoncé's mom, Tina, for 30 years. Fun fact: Mathew and Alexsandra's son, Nixon, is younger than his nephew, Solange's five-year-old son, Daniel. That's classy, Mathew. For the record, our stance on sex outside of marriage is that if it's okay with both people in the marriage, then go forth and shag freely. But we've never heard of one partner being okay with the other partner having a baby with someone else. Because that's tacky.
7. Anne Boleyn
In a way, Anne Boleyn was kind of the best mistress of all time. She was certainly one of the most influential. The lure of Anne's ladybits was so powerful that Henry VIII basically took apart the Catholic Church in England in order to have his marriage to Catherine of Aragon annulled so he could marry Anne and (he hoped) father a legitimate male heir to the throne by her. That...didn't work out so well. And once Henry tired of her, he had his ministers cook up the story that she'd slept with her brother, George, and so Henry had both Anne and George beheaded. Yikes. We bet all the ladies on this list feel lucky that the dudes they cheated with don't have the power to shriek "Off with her head!"
Photo of Tiger mistress Cori Rist via Bauer-Griffin.