Madonna’s Sex Life In Pictures: A Look Back At The Men, Women, And Other Things She’s Dated

Madonna’s had a lot of much-publicized relationships during her time as the reigning Queen of Pop and, now, as a musical footnote intent on keeping herself in tabloids.

It’s telling that she is now arguably more famous for her relationships — and current divorce — than anything else. Madonna’s dating pool is quite diverse and has all sorts of interesting clumpbs of things floating about within it. So let’s take a trip down memory lane and look at all the suitors — the men, the women, the disgruntled oxen — that Madonna has boffed on her journey to the top:

Tony Ward

We had to look this person up. He is apparently a “model, actor, fashion designer, painter and photographer” from LA, which meant the poor thing was unemployed. He has, however, appeared in some films and videos over the years, include a few of Madonna’s and Bruce LaBruce’s Hustler White. He is currently married with three children: Tora Dali, Lilli Tatsu and Ruby Love.

Vanilla Ice

Perhaps she got frosted.

Mark Wahlberg

Did you know he has a tertiary nipple?

Tupac Shakur

For all we know, she’s probably still dating him.

Jenny Shimizu

This former Calvin Klein model also dated Angelina Jolie. She must have a thing for women with affected accents and penchants for adopting tiny children.

Henry Rollins

Dennis Rodman

At least they could borrow each other’s jock straps.

Sean Penn

These two were married. Which probably means Hugo Chavez got Madonna cooties last time he and Sean made out.

Esai Morales

Esai is a cool name. He was in La Bamba and Allstate insurance commercials. Jealous?

Lenny Kravitz

Later, Lenny would go on to allegedly dip his nuggets in Cynthia Rodriguez’s sweet & sour sauce.

Ingrid Casares

Cubans do do it better.

Carlos Leon

…See?

David Blaine

Sandra Bernhard

We’re developing fucking Carpal Tunnel Syndrome now. God. Seriously, fuck Madonna.

Alex Rodriguez

Our hand is totally numb.

Jose Canseco

Who wouldn’t want Jose’s baby batter all up in their business?

Madonna [LA Times]