Since Madonna first set the music world alight in 1983, men and women everywhere have fallen for the charms of one of pop’s sexiest women.

Now, as she celebrates her 50th birthday on 16 August and a quarter of a century as one of the most provocative and seductive artists of all time, we delve into Madonna’s sex files to uncover some of the more noteworthy men (and women) to get up close and personal with the pop siren.

John “Jellybean” Benitez
During the early 80s, the then-DJ and mixer gave Madonna a leg-up and a whole lot more on her climb to the top of the fame ladder, becoming involved with producing and remixing tracks on Madonna's debut album, including ‘Everybody’, ‘Borderline’, ‘Lucky Star’, and ‘Holiday’. Their relationship lasted for about two years until she eventually moved on. I won’t make an obvious and crude joke here about Madonna flicking her bean. Oh wait, I think I just did.

Sean Penn
It was love at first sight when Madonna met the actor and her future husband on the set of her video for ‘Material Girl’, in which she emulated Marilyn Monroe. But it was a marriage doomed to fail – attention seeker Madonna welcomed the photographers, Sean beat them up. The couple’s volatile relationship with the media earned them the nickname “The Poison Penns” while they were filming Shanghai Surprise. Actually, the less said about that film, the better.

Sandra Bernhard
Whether or not a lesbian affair actually happened between Madonna and the comedienne, the pair certainly wanted the world to think so. In 1988, when they appeared on Late Night with David Letterman, they told Letterman he could only hang out with them if he had a sex change and that they frequented a notorious lesbian bar in the Village. A year later, they performed Sonny and Cher’s ‘I Got You Babe’ together at a benefit. Their highly publicised double act is a perfect example of Madonna knowing exactly how to titillate and tease her audience.

Warren Beatty
But what about Dick Tracy? Dick, that’s an interesting name… Taking her passion for old movie stars to the next level, Madonna bagged one for herself when Warren came onto the scene. Going where the likes of Julie Christie, Diane Keaton and Natalie Wood had all gone before, Madonna cemented her status as one of the world’s most desirable women and seductresses. As she sang on the soundtrack to their movie, Dick Tracy, “I always get my man”. We don’t doubt it!

Ingrid Casares
In his book, Life With My Sister Madonna, Christopher Ciccone describes Ingrid as “the man in Madonna’s life” from the night they met in 1991 up until Madonna married Guy Ritchie. He goes on to say, “It wouldn’t have surprised me at all if my sister and Ingrid were having intimate relations”, and that Ingrid gave Madonna “the deepest, most enduring liaison of her entire life”. Camille Paglia, however, was less than complimentary about the close relationship: “She’s turned into Madonna’s flunky and yes-girl….Madonna should go to the Betty Ford clinic to break her addiction and detox from Ingrid”. Nonetheless, for Ingrid to stay at Madonna’s side for all those years proves that this “yes-girl” sure has stamina.

Robert Van Winkle aka Vanilla Ice
Okay, Vanilla Ice was sizzling hot in his hey day, so who can blame Madonna for snapping up the rapper during his 15 minutes of fame? They had an eight month relationship during which the lucky man received the full force of Madonna’s brazen sexuality and exhibitionism, appearing in her Sex book. In 1994, when USA Today asked him if she was a sexual animal, he replied, “Nah, she's like every normal girl, man. She's very sexy, she's hot, she's romantic.”

Jenny Shimizu
In 2007, the gay model and Dante’s Cove actress, who "married" Rebecca Loos in a TV wedding in 2005, revealed that she once had a hot and steamy fling with Madonna. She claimed that Madonna would fly her across the world so the two of them could get it on: “I was her secret booty call, available any time of the day or night for secret sex sessions”. Phwoarrr! Jenny then went on to add, “She’s sensational in bed”. Well, we could have guessed that last part ourselves, Jenny!

Dennis Rodman
Basketball’s bad boy also praised Madonna’s sexual prowess when he wrote about their 1994 fling in his autobiography. But the memory of great sex wasn’t the only thing D-Rod took away from the affair. He also said he learnt all about self-promotion from the woman herself, getting piercings and tattoos, as well as painting his hair. Madonna told ‘USA Today’, "I love Dennis Rodman. He's hot. I adore him. He's a rebel, the Madonna of the NBA." Two peas in a pod, or a rod, then.

Carlos Leon
Madonna met the father of her first child, Lourdes, in Central Park in 1994. He soon became both her trainer and lover. Talk about a great day in the park! And boy, we’re betting Carlos sure kept her fit. Carlos apparently sports a tattoo that reads, “September 8 Forever”, the day he met Madonna. “That’s the day my whole life changed”, he explains.

Guy Ritchie
Madonna met the director in 1999, after which they married and had a son, Rocco. Despite the “will they, won’t they” divorce controversy currently swirling around them, Guy must have been doing something right during the course of their marriage. Madonna’s love song ‘I Deserve It’, from her 2000 album Music, described a romance in which her lover has danced for her and she for him. In real life, Madonna has lovingly danced for and taken direction from Guy not once, but twice. He directed her performances in the video to ‘What It Feels Like For a Girl’ and the film Swept Away. Actually, again, the less said about that film, the better…

Love Madonna? Buy her latest album Hard Candy online now. You'll save money to put towards Christopher Ciccone's controversial new book, Life With My Sister Madonna.

Want more? Give our Madonna Unwrapped Quiz a try and check out the video for her latest single, 'Give It 2 Me', below!