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MADONNA WEEK: Top 10 Hottest Lovers, Husbands and Flings

It’s Madonna Week on AwardsWatch! With the Queen of Pop celebrating her 56th birthday on August 16th, we’ll be counting down and charting everything from her relationships to videos to #1 singles, all leading up to a rated, reviewed and ranked chart of her 12 studio albums.

Today we’re starting off with Madonna Top 10 Lovers, Husbands and Flings. Madge has always been notorious for her swinging ways but did manage to settle down twice. But not for long as both marriages, first a stormy and violent romance to Sean Penn and a distant and cold relationship with Guy Ritchie, both ended in divorce.

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10. Sandra Bernhard – DATED – 1989
Coming in at #10 is Madonna’s most public romance with a woman, Sandra Bernhard. Yeah, Bernhard kinda looks like she got run over by a truck but theirs was a friendship first that turned into a romance and then bridges were burned and the two separated and were never friends again. They’re appearance on David Letterman was infamous.

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09. Warren Beatty – DATED – 1989 -1990
After meeting on the set of Dick Tracy, star and director hit it off behind the scenes as well. The notoriously recluse Warren Beatty even made an appearance in Madonna’s 1990 concert film Truth or Dare, where you could see the unraveling take place as her openly ridiculed her lifestyle (“Why would you LIVE off camera?”). It was a whirlwind romance but clearly not destined for the test of time.

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08. Lenny Kravitz – DATED – 1990
A mostly quiet and non-publicized pairing, Lenny Kravitz was sort of the beginning of Madonna’s attraction to Latin and African-American men. And why not, Kravitz is fucking hot.

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07. Carlos Leon – DATED – 1994 -1997
Sometimes when you start dating your physical trainer you get really good, energetic sex. Other times, like Madonna and Carlos Leon, you produce a gorgeous and stunning child (Lourdes, now 17). It was also a high point of creativity for Madonna. During this period she starred in Evita, winning a Best Actress Golden Globe for the role and beginning work on what is largely considered the best album of her career, Ray of Light. This was Madonna’s longest non-marriage relationship and even though they only managed to stay together another year after Lourdes was born, the two remain close. Even very close during Madonna’s break-up with husband #2, Guy Ritchie.

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06. Sean Penn – MARRIED – 1985 -1989
At times, this tumultuous relationship looked it was going to go from Burton and Taylor to Bonnie and Clyde. Madonna, at the beginning of a huge career and Penn, a highly respected actor but with an explosive temper. Their beachside wedding was a high point of pre-TMZ paparazzi journalism but it was Penn’s temper and violence (including against Madonna herself) that spoiled the pairing. Still, Madonna noted in 1990 that Penn was the love of her life.

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05. Jesus Luz – DATED – 2009 – 2010
As Madonna gets older the boyfriends get younger and younger and good for her! Setting no boundaries of age or race or social status, Madonna dated supermodel Jesus Luz briefly and he appeared in her Celebration music video. He’s also hot as balls.

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04. Ingrid Casares – DATED – 1992 -1994
One of Madonna’s many lady loves and the longest relationship with a woman she’s had. Ironically, she met Casares through previous fling Sandra Bernhard whom Casares was dating at the time. And shady as it was, Madge snatched her away for herself.

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03. Tony Ward – DATED – 1990 -1991
Dating model Tony Ward was an easy choice. He was an up and coming model (at the time), starred in her music video for Justify My Love and was really hot. Enough said.

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02. Guy Ritchie – MARRIED – 2000 – 2008
Madonna’s 2nd marriage and longest relationship. It began as “flawless,” according to Madonna herself but soon she said saw  “cracks in the veneer.” The union produced a remake of the 1974 Lina Wertmüller film Swept Away, a disastrous affair that was savaged both critically and commercially. But it also produced another child for Madonna, Rocco (now 14), a great joy in her life.

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01. John F. Kennedy, Jr. – DATED – 1987-1988
A very fast romance but, with the mortality rate of the Kennedy clan, probably a good thing. But it’s probably safe to say that anyone that ever dated JFK Jr. hit a high point of hotness with him. When he asked Madonna to pose as his mother on the cover of his George magazine she replied: “Dear Johnny Boy, Thanks for asking me to be your mother but I could never do her justice. My eyebrows aren’t thick enough, for one. When you want me to portray Eva Braun or Pamela Harriman, I might say yes! Hope you’re well. Love, Madonna”

About Erik Anderson

Erik blames his mother for his love of all things Oscar, having watched them together since he opened his eyes. They also watched Miss Universe religiously every year (the pageantry!) and Erik came to the conclusion that the combination of these two things ultimately led him down the path to obsessing about awards and ACTRESSING. He began at GoldDerby, led by Tom O’Neill and then migrated over to Oscarwatch (now AwardsDaily), headed up by Sasha Stone before breaking off to create AwardsWatch. He is a member of the International Cinephile Society, GALECA (The Society of LGBTQ Entertainment Critics), the International Press Academy and is the founder/owner of AwardsWatch.