It’s fun to go back in time and reminisce about who-dated-who in Hollywood. Some relationships we’ve forgotten about, and others are so hush-hush that they weren’t even common knowledge to begin with. The men get most of the credit for their hook-ups. Charlie Sheen probably holds the record for the most partners. Brad Pitt has the most hyped relationships. And George Clooney is known the world over for being a serial monogamist. But what about Hollywood women? Taylor Swift is the woman that jumps to mind right now for having the most hook-ups in the shortest amount of time. But Cameron Diaz and Jennifer Love Hewitt have also been with their fair share of men. However, none of that is too shocking. Men dating women, and women dating men… no big deal.
What’s way more juicy is reviewing the women that female stars have hooked up with. And no one has been with more women that the Material Girl, Madonna. Her love life is legendary, and spans decades. Always one to push the envelope, she continues to challenge stereotypes of love and sex in the most delicious ways. Her little black book is filled with women fitting every description, from the masculine-women with cropped hair to the girlie-girls with lipstick. Whether it is kissing, touching or more, Madonna always pursues her innermost desires. And we, as the public, are fortunate enough to have front row seats to her hedonism.
Everyone knows about her marriages to Sean Penn and Guy Ritchie, her flings with sports stars Dennis Rodman, Jose Canseco and A-Rod, and her romances with Warren Beatty and JFK, Jr. What most people still don’t know about are her girl-on-girl encounters. So lick your lips, because you will cherish this list, find it to be true blue and find that we will justify your love for all things Madonna.
15 Moira McFarland
Every diehard Madonna fan knows who Moira McFarland is – she was Madonna’s best friend growing up and was featured in the documentary Truth or Dare reuniting with Madonna. Even in her youth, Madonna was always experimental and breaking boundaries. She smoked, she drank and performed as a go-go dancer in a school recital. She also revealed that she had relations with McFarland in high school.
McFarland has said that she had no recollection of the event; however, she also said that she did a lot of drugs over the years which impaired her memory. Madonna apparently remembered a lot more of the details of her time with her “childhood idol.” She said the two of them shared McFarland’s parents’ bed which was two twin beds pushed together, that they jumped around naked together, and that McFarland taught her how to use a tampon. Although the two were estranged for years, McFarland apparently retained strong feelings for Madonna. She wrote her letters, and asked Madonna to be to godmother of one of her children.
14 Debi Mazar
Actress Debi Mazar (far right) has been friends with Madonna since the two were both unknowns living in New York. They met in an elevator and started dancing, and the rest is history. Mazar even appeared in Madonna’s music videos, including Papa Don’t Preach, Deeper and Deeper and the explicit Justify My Love. The two were always super close, but they got downright cozy in a pictorial they shot for Rolling Stone where they were French kissing.
Many people perceived their on-camera hook-up to be a case of art imitating life. Although nothing has ever been confirmed, many believe that Madonna and Mazar have hooked up plenty of times over the years. And we can’t blame them, as both have made careers out of oozing sexuality. Plus, Madonna isn’t really known for having a lot of gal pals, so it’s only natural to surmise that her relationship with Mazar wasn’t entirely platonic.
13 Rosanna Arquette
Rosanna Arquette starred alongside Madonna in the 1985 movie Desperately Seeking Susan. It was Madonna’s first major screen role. Although the film wasn’t a success, it has had a long cult following due to how alluring the women were on screen. Madonna was described as being a “trampy goddess” and Arquette is still known as being the most attractive Arquette due to her doe eyes, full lips and thin build. In 1985, Madonna was still making a name for herself and finding her way in the entertainment business. Thus, she wasn’t as open with her relationships – especially those involving women. But now that the public has a better idea of her tastes, tongues have been wagging particularly hard that she hooked up with Arquette. The chemistry between the two women is undeniable on camera, so it’s hard to believe that they never experienced intimacy in their private lives.
12 Sandra Bernhard
The most notorious of all Madonna’s female relationships has got to be the one she had with comedian Sandra Bernhard. The two were very chummy, and even appeared together in matching outfits. Bernhard was completely out as a lesbian, so everyone figured that she had her eye on Madonna. Madonna was more than happy to play up to that notion. They made headlines when they appeared together in 1988 on Letterman. They were touchy-feely, and flirted shamelessly with Letterman and each other. After that, everyone considered them to be an item. They always made jokes about hooking up, and talked in innuendo.
Eventually the two of them had a massive falling out. It got so ugly that people thought for sure that it was a break-up between lovers, and not just a disagreement between friends. Madonna shrugged it off soon enough, but Bernhard held a grudge. She slammed Madonna in her performances for years, and even accused the superstar of stealing her girlfriend.
11 Ingrid Casares
Remember how we told you that Sandra Bernhard accused Madonna of stealing her girlfriend? Well, that woman’s name is Ingrid Casares (left). And she definitely makes the list for Madonna’s hottest female hook-ups. It’s been said that she resembles a lesbian Audrey Hepburn, and that she’s a gay cultural icon. According to Madonna’s brother, Casares had a relationship with Madonna that lasted for years; he believed it to be sexual. It’s true that Casares used to be Bernhard’s girlfriend, and that things ended between the two once Madonna entered the picture. Casares was soon a fixture in Madonna’s entourage, and even reporters wrote that they were witnessed en flagrante. Casares has been characterized as a perfect partner for Madonna because she would never fail to agree with the star. Although the two have now gone their separate ways, they will be forever immortalized in photos, from Madonna’s sex book to paparazzi pics.
10 Jenny Shimizu
Model Jenny Shimizu is most well known for having been in a sexual relationship with Angelina Jolie. According to Shimizu, she was also in one with Madonna – at the same time she was hooking up with Angelina! Shimizu seems to be one that likes to kiss and tell, so she has spilled the beans on being with Madonna.
She has said that Madonna treated her like a “sex slave” and that she made herself available to the Material Girl at all hours for booty calls. She also said that Madonna was “sensational” in bed. Shimizu certainly gets around, as she has been linked to actresses Ione Skye and Rebecca Loos (who claimed to have had an affair with David Beckham). It seems like all these women get around, so fans are crossing their fingers that Madonna’s next conquest will be a newly single Jolie. That would be the celebrity news story to end all news stories!
9 Alanis Morissette
Alanis Morissette was linked to Madonna back in the 90s. This was when Madonna’s record label, Maverick, signed a young Morissette. Madonna was very open with her praise of Morissette’s work, and even stated that Morissette reminded her of a younger version of herself. Morissette was equally complimentary of Madonna, and spoke of the fact that they are both “aggressive women.”
Madonna is known for working closely with the artists she mentors – very closely. So, legend has it that she put the moves on Morissette just like she did with musicians like Tupac Shakur and Vanilla Ice. Morissette has never been considered a beauty, but her masculine looks sparked gossip that perhaps she enjoyed women. Although Morissette has never commented about the gossip, we do know that she admitted to be promiscuous during her first tour. She is quoted as having said that she and her band mates had a contest to see who could sleep with the most people. No word on who the winner was, though!
8 Gwyneth Paltrow
Madonna and Gwyneth Paltrow became fast friends when Paltrow’s star was on the rise. They were photographed doing everything together – and we mean everything. They worked out together, went to fashion shows together, and partied together. They were photographed numerous times kissing one another in a way that blurred the lines between a friendly peck and a full-on mouth kiss.
Like many of Madonna’s relationships, her friendship with Paltrow crashed and burned. Some rumors attributed the falling out to Paltrow’s refusal to convert to Kabbalah, while others said it was an argument over their shared personal trainer. However, the most imaginative theory is that the two were secretly lovers and had a bad break up. Paltrow seems like an ice queen, but we bet even Madonna could melt her. Plus, the rumor mill is rampant with the unspeakable deeds she did with Brad Pitt when they were together – so it’s not a stretch that she would become intimate with Madonna.
7 Kelly Osbourne
Kelly Osbourne covered Madonna’s hit song “Papa Don’t Preach,” which many thought was a landmark move since Madonna is fiercely protective of her work. Years later, Osbourne promoted Madonna’s Material Girl fashion line. All of this synergy sparked a debate about whether or not Madonna and Osbourne hooked up. Since Madonna has such a long list of conquests, the odds probably favor that they did. Plus, Osbourne has been suspected of being bisexual for years, and she fits in with Madonna’s type of hooking up with ladies with short hair. Now that Sharon Osbourne has disclosed that she is bisexual, many are thinking that the apple doesn’t fall far from the tree. Pictured with Lourdes, Madonna's daughter, on the left.
6 Britney Spears & Christina Aguilera
Madonna managed to do the unthinkable in 2003. She hooked up with Britney Spears and Christina Aguilera on stage during the MTV Video Music Awards. The build-up was unbelievable. The whole thing started with Spears singing Like a Virgin. Then, she was unexpectedly joined by Aguilera who popped up out of a wedding cake. The piece de resistance was Madonna joining the pair, and kissing the two girls at the end. The hook-up was aired over and over again. Much was made out of the kisses. Some people thought Spears gave Madonna an erotic kiss, whereas Aguilera came across as trashy. Others were mad that Aguilera got sloppy seconds. But everyone agreed it was hot. Of course the whole thing was for publicity… or was it?
A savvy viewer of the performance will notice that there is a lot chemistry between Madonna and the girls. Madonna removed Aguilera’s garter belt, which is a very intimate gesture. Also, Madonna placed her top hat on Spears, which was seen as a sexy domination of her. And what further cemented the notion that Madonna really did hook up with Spears was their performance together in the music video Me Against The Music. It depicted the two of them getting very steamy.
5 Missy Elliott
There’s one thing that is often forgotten about the VMA performance when Madonna kissed Britney Spears and Christina Aguilera – it’s that Missy Elliott also came out on stage and performed with the girls! She was viewed as the officiator of the “ceremony.” At the time, many people joked that she should have gotten in on the action. When asked why she didn’t join in, Missy Elliott reportedly acted aghast at the notion. She was quickly forgotten as she was overshadowed. But fast forward several years, and Missy Elliott came out as a lesbian, and even married a woman.
Suddenly, her presence during the performance didn’t seem so innocuous anymore. And those with good memories will recall that Madonna and Missy Elliott appeared alongside one another in a Gap commercial the same year as the VMA show. They danced together, bumped butts, and were hanging all over one another. They even collaborated on Madonna’s song “Hollywood.” At the time it seemed like a really odd pairing, but now the pieces seem to be falling into place… While we don’t know if the two were friends with benefits or not, it’s a safe bet.
4 Hard Candy Tour Female Dancers
When Madonna was on her Sweet and Sticky tour to promote her album Hard Candy, she made a point to hook up with one of her female dancers during every show. She would take a huge swig from a bottle of champagne, then would eye up a dancer, and then would pull her in for a heavy kiss. While many people think this display was just for show and to appeal to younger audiences, others were certain that it was simply symbolic of what was going on behind the scenes while on tour. Madonna is known for being wild while on the road, and has had relationships with members of her entourage. So, it follows that she did more than just kiss her female dancers.
3 Miley Cyrus
Miley Cyrus is much younger than Madonna – which totally fits in with Madge’s M.O. Add to that the fact that Cyrus is in her experimental stage, and most people read between the lines and assumed that they hooked up. The two performed “Don’t Tell Me/We Can’t Stop” together, and it was an odd tableau. Madonna looked like she was dominating Cyrus, and Cyrus looked like a little boy that was all too eager to take it. Cyrus openly flirted on stage with Madonna, and made a lot of lascivious motions while the two were dancing. Cyrus even photoshopped a pic of her and Madonna locking lips afterwards. It’s inferred that Madonna took her up on that offer. And don’t think that Madonna has mellowed with age. Even when she was still married to Guy Ritchie, she was photographed at an adult shop buying merchandise that was only suitable for two women to use.
2 Katy Perry
Katy Perry made a cameo in Madonna’s music video, “B*tch, I’m Madonna.” So did a lot of other stars, but Perry was featured in two shots which none of the other stars were. So, when Katy Perry joined Madonna on her Rebel Heart tour, many people thought they got to know each other a little too well. That’s because they bumped and grinded on stage, and posed for provocative pics together. They even shared a drink from the infamous “banana flask,” which was rather suggestive due to its shape and size. Knowing how touchy-feely Madonna is, many fans figured the two ladies hooked up. Right now, Madonna has neither confirmed nor denied anything. We guess we’ll just have to wait for her to come out with her second sex book.
1 Lady Gaga
Lady Gaga (right) and Madonna have a lot in common, as they are both music superstars and like to shock the general public. Lady Gaga has openly confessed to being bisexual, and Madonna is regarded as being bi as well. The media had a field day pitting them against one another, and Madonna added fuel to the fire when she claimed Lady Gaga’s song “Born This Way” was a rip off of her song “Express Yourself.”
However, they have reportedly buried the hatchet and were photographed together at the Met Gala in 2015. The pic was too much for many to handle, as Lady Gaga was on one side of Madonna, and Katy Perry was on the other. Perry is known for her song “I Kissed A Girl,” and has admitted that she’s kissed plenty of them. Many people did the math in their heads and saw that these three celebs are all attracted to girls… Madonna loves variety and most figured that she was “connecting” with both women – probably at the same time.