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.
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.
13 Rosanna Arquette
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.
11 Ingrid Casares
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.
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.”
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.
7 Kelly Osbourne
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?
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.
4 Hard Candy Tour Female Dancers
3 Miley Cyrus
2 Katy Perry
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.
Sources: People, Telegraph, TheGuardian
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