Happy Birthday, Madonna! A Look Back At 10 Of The Queen’s Hottest Boy Toys

Today, the Queen of Pop, Madonna, turns 55.

Yes, 55.

We can hardly believe it ourselves. Not only because she looks fantastic, but because —well — we don’t even want to think about how old that makes us.

In honor of the hit maker’s milestone birthday, we thought we’d look back at some of the men she’s dated and/or hung out with, worked with, employed as models/dancers, all of the above, over the years. Looking at these men, we see she shares more than just a gay sensibility with us. She shares our taste in men – bad boys — and her relationships tend to be even shorter than ours.

If only we could look back at such a harem of studs by the time we reach 55.

We couldn’t include them all (obviously!), but here are our top 10 picks…



Photo credit: Madonna.com


Joey Stefano

Joey Stefano made a name for himself in the gay porn industry in the late ’80s and early ’90s. His mad bottoming skills caught the attention of Madonna, who asked him to model in her now-infamous 1992 Sex book, which accompanied her album Erotica. The two shot several scandalous pictures together for the book, which has since become a much sought-after collector’s item.

Photo credit: Moon shot.


Dennis Rodman

Okay, okay. So Dennis Rodman may not be everyone’s cup of tea. The tattoos, the body piercings, the questionable hair colors, the cross-dressing. It can all be a bit much. But you can’t deny he’s got an amazing body. And at 6’7, he’s one very tall glass of water — and in his prime was a fabulous bisexual defender and rebounder as well. It’s no wonder Madonna couldn’t keep her paws off him for two months back in 1994.

In his 1996 memoir Bad As I Wanna Be, the former NBA player wrote some rather graphic accounts about their short-lived relationship (we use that word lightly), which included quotes from her raunchy love notes that we can’t re-print here (which speaks volumes).


While we’re on the subject of athletes, in 2008 rumors began flying that Madonna and New York Yankees third baseman Alex Rodriguez were hooking up. In fact, some sources reported that he was the main reason for her split with Guy Ritchie. Whether or not this was true has never been confirmed. Both Madonna and A-Rod’s camp remained mum about the alleged relationship, and the two were never actually seen out in public together. But given Madonna’s taste for men who are built like Greek gods, we wouldn’t be surprised if it were true. (Even if we were later to discover that the body — and home run skills — was chemically enhanced.)

Photo credit: The Berry

Adrien Galo

Alright, so technically Madonna never actually dated Adrien Galo, as far as we know. He was just her backup dancer on her 2012 MDNA tour. But we wanted to include him on our list because… well… look at it! Those abs. Those biceps. Those underwear. Yum.

Photo credit: alanilagan.com

JFK, Jr.

Over the years, Madonna has frequently drawn inspiration from Marilyn Monroe, from channeling the blonde bombshell’s signature style in her Material Girl music video, to dating Marilyn’s former lover’s son, JFK, Jr.

Madonna and JFK, Jr. first met in 1987, after her divorce from Sean Penn. They were together for about a year before they called it quits, though they were rumored to have hooked up a few more times the ’90s. Strictly on a “friends with benefits” basis, of course.

Years later, the whole romance took a slightly creepy turn when, in 2012,  it was released that Kennedy had wanted Madonna to pose as his mother, Jackie O., in George magazine in 1996. (Madonna declined the offer.)

Jesus Luz

Speaking of mommy complexes… Madonna met Brazilian model Jesus Luz on a 2009 photo shoot for W magazine. She was 50; he was 22. Despite a 28 year age difference, the couple hit it off and embarked on a passionate two year romance that had many people scratching their heads. After all, you can’t deny there’s something just a little bit unsettling about their two names paired with the fact that she was old enough to be his mother.

Photo credit: W Magazine.

Jull Weber

Yee-haw! In addition to accompanying Madonna on her 2001 Drowned World tour, Jull Weber also starred as one of the hot cowboy dancers in her Don’t Tell Me music video. Wouldn’t you just love to strap a saddle on this sexy Puerto Rican and ride him all the way to the dawn?!

Photo credit: Jull Weber.

Tony Ward

Actor/model Tony Ward and Madonna dated in the early 1990s, during the height of her sex-crazed dominatrix potty mouth era. He was featured in both her Justify My Love and Erotica music videos, as well as in her now infamous 1992 Sex book. His relationship with Madonna is probably the best thing that ever happened to his career. Unfortunately, after they split, Tony struggled to find work, appearing in a few low-budget B-movies before falling into obscurity.

Want to see some NSFW photos of Tony in his prime? Go here.

Guy Ritchie

Filmmaker Guy Ritchie may not be as chiseled as some of Madonna’s other lovers, but what he lacks in a six-pack he makes up for with his sexy English accent and he looks great in a slouchy black leather jacket.

He and Madonna were married from 2000-2008, during which she developed a faux British accent and tried to reinvent herself as an unconvincing English country lady, buying a manor house in Wiltshire and taking up horseback riding.

At the same time, Guy’s film career began stalling. He directed a string of flops, including 2002’s disastrous Swept Away, which starred the Queen of Pop, and 2005’s Revolver, which pulled in a lackluster $6 million at the box office and was universally panned by critics.

After the pair split in 2008, Madonna dropped the accent and moved back to the states. Meanwhile, Guy’s film career took off again. His next two films garnered over $1 billion worldwide even though they are really quite awful remakes of Sherlock Holmes movies.

Photo credit: ifitandhealthy

Brahim Zaibat

We thought we’d round out our list with the current man in Madonna’s life, 24-year-old Brahim Zaibat. The couple met shortly after she broke things off with Jesus Luz. Brahim performed in Madonna’s 2012 Superbowl halftime show, then hit the road with her for her MDNA tour last summer. They’ve been together for a while now, and they don’t show signs of breaking up.

Has the Queen finally met her Prince Charming?

Photo credit: MSN