Madonna turns 66: inside her complex love life and blended family

At the height of her fame in the 80s and 90s, Madonna dated men as varied and dynamic as her career. 

She was with Jean-Michel Basquiat, one of the foremost artists of the 20th century, for a year between 1982 and 1983 before meeting and marrying I Am Sam actor Sean Penn.

In the 90s, Madonna and actor Warren Beatty had a highly publicized relationship after meeting on the set of their film Dick Tracy in 1989. 

Despite only dating for 15 months, Warren gushed about his ex to People in 2016: "She's a huge personality, diligent and disciplined and a spectacular dancer and performer," he said. "She's a phenomenon."

She also dated rapper Vanilla Ice for eight months in 1991 and rapper Tupac Shakur in the mid-90s before their split. 

She briefly moved on to basketball star Dennis Rodman, followed by a fling with John F Kennedy Jr. 

Madge met actor Sean Penn in 1985, on the set of her music video for 'Material Girl', and the pair quickly fell in love. Their whirlwind romance was passionate, and they married just six months after meeting. 

They went on to star alongside each other in the 1986 film Shanghai Surprise, but their marriage was on the rocks. 

Madonna filed for divorce in 1987 before withdrawing the petition, and again in 1989 for the final time, with her rep telling People, "There was no one direct incident leading up to this."

"It was a series of cumulative pressures. There were many moments in their marriage when it was shaky, and Madonna was finally forced to face the reality of the situation-- that they weren't happy together."

A pervasive rumor began to spread that he had allegedly abused her during the marriage. Madonna finally shut this down in 2016 when she wrote a statement in defence of Penn for a trial in which he sued Empire creator Lee Daniels for defamation. 

She wrote, "While we certainly had more than one heated argument during our marriage, Sean has never struck me, 'tied me up,' or physically assaulted me, and any report to the contrary is completely outrageous, malicious, reckless and false."

The pair remain friends to this day; the 'Like A Prayer' singer even supported her ex-husband at his Help Haiti Home gala in 2016. 

"I want to say, Sean, I love you from the moment that I laid eyes on you," Madonna said in a speech at the event. "I just wish you'd stop smoking cigarettes," she joked. 

Madonna and Sherlock Holmes director Guy Ritchie met through The Police's Sting and his wife Trudie at a party of theirs in 1999. Madonna told People that during their first encounter the Brit instantly caught her eye: "I had a whole premonition of my life fast-forward," she said. 

"My head didn't just turn; my head spun round on my body. I was taken by his confidence. He was sort of cocky but in a self-aware way… He's a risk taker, and he's got a hungry mind."

The pair welcomed their son, Rocco, on August 11, 2000, and were married in Scotland in December 2000. They were married for eight years before calling it quits, and they only had kind words for each other in the aftermath. 

Guy told Details magazine in 2011, "I enjoyed my first marriage. It's definitely not something I regret. The experience was ultimately very positive." 

Madonna spoke to Newsweek about the reality of their marriage in 2012, detailing that "When you start off, everything's great and lovely, and the person you've married is flawless, and you're flawless. Then time goes by, and you share a life, you have children, and there are cracks in the veneer."

"It's not as romantic as it used to be. You think, 'This isn't what I thought it was going to be,' and 'How much am I willing to sacrifice?'"

Despite Guy calling their marriage a "soap opera", it wasn't until 2015 that the pair had bad blood. Madonna and Guy entered into a custody battle over Rocco, as he wanted to live in London with his father. 

Madonna's first child, Lourdes, is the spitting image of her mother; she was born in 1996 to the seven-time Grammy winner and her boyfriend, fitness trainer Carlos Leon. Sadly, Lourdes' parents split just a year later. 

The eldest of Madonna's brood is a successful model in her own right; she has worked with the likes of Marc Jacobs, Burberry and Rihanna's Savage x Fenty. 

She credits her mother for helping her pave her own path, separate from Madonna's legacy. "Obviously, I grew up with extreme privilege. There’s no denying that. But I think my mom saw all these other kids of famous people, and she was like, 'My kids are not going to be like this'," she told Interview in 2021. 

"Also, I feel like if your parents pay for things, then it gives them leverage over you. My mom is such a control freak, and she has controlled me my whole life."

Despite her strict upbringing, Lourdes is close to her mom and appreciates the impact she had on culture. "I didn't fully comprehend that until I realized the importance of empowerment and what it means to be a woman," she told Interview.

"She's probably the hardest worker I've ever seen. I didn't inherit that, unfortunately. I inherited her control issues but not her work ethic!"

Where Lourdes and Madonna could be twins, Rocco and his dad, Guy Ritchie, are carbon copies of each other. Rocco was born five months before his parents were married and is close to both Madonna and Guy.

His decision to live with his dad and attend school in London created a rift between his parents in 2015, leading to a custody battle over where he would reside. 

Madonna alleged that he was being held in England by his dad and even dedicated a 'La Vie en Rose' performance to him during her 2016 tour. 

"There's no love stronger than a mother for her son, and if I talk about him too much, I'm going to cry," she said during the show. "I hope he hears this somewhere, and he knows how much I miss him."

The custody battle was eventually settled, and Rocco stayed in the UK to complete his schooling; he told Vogue Hong Kong that the decision had changed his life for the better. 

"It was the perfect moment; I was shifting gears from a teenage boy to a young man, and it pushed me to focus on my passion but to also get out of my comfort zone."

He studied at the Royal Darwin School and is now an artist. He recently had an exhibition in Miami, which his mother and siblings attended. 

David and Madonna first crossed paths when she founded the charity Raising Malawi in 2006 and visited the country to further her humanitarian efforts. It was in an orphanage that she met her son, who was one year old at the time. 

Despite initially completing the process of adopting David with Guy, Madonna and her husband divorced before the adoption was finalized in 2008. 

Now, David is a musician and often joins his mother on stage or at fashion shows. Madonna couldn't praise her son enough when speaking to Jimmy Fallon in 2022, gushing that "he can put on any outfit and look swag as you know what"

"It's really irritating. He wears my clothes and looks better in them."

The 66-year-old revealed to British Vogue that she has the most in common with her third child and that "he has more of my DNA than any of my children so far"; he now offers song writing sessions and guitar lessons and seems to be following in Madonna's musical footsteps.

Mercy, otherwise known as Chifundo James, was Madonna's second adopted child and also hails from Malawi, like David. 

She was officially adopted in June 2009, when she was three years old, and grew up to be a piano aficionado, even playing at some of her mother's concerts.

The Evita actress gushed about her daughter on Mercy's 18th birthday this year in a lengthy Instagram post detailing how proud she was.

 She revealed, "You surprised all of us! You were always the quiet one. The gentle one. The shy and stoic one. While all of my other children were clamoring for attention, you were hiding under your hoodie – never wanting to draw attention to yourself." 

"Always humble and kind, always the first one to say thank you. To clear the table after dinner! To come and hug me and say how much you appreciate something. And always the most responsible."

She continued, "To watch how you care for your younger sisters. To see you unfold from a chrysalis to a butterfly. Beautiful Chifundo James, nothing gives me greater pleasure than to watch you grow. You really are a wonder."

The youngest children of Madonna's brood were born in Malawi in 2012 and adopted by the singer in 2017. 

She revealed to People why she chose to add to her growing family with these girls, saying, "Sometimes I would just close my eyes and just think, 'Why isn't my kitchen filled with dancing children?' There's so many children that need a home. I thought, 'What am I waiting for? Just do it.'"

In an Instagram tribute for their 11th birthday, Madonna gushed about her little girls, reminiscing about their first meeting. 

"I will never forget the first time we met you in Machinji," she wrote. "Your eyes held the whole world in them. The same way we now hold you locked inside of our hearts."

The twins are following in their sibling's footsteps; Stella loves to play the piano, and Estere is a talented dancer. Estere also joined her mom on her Celebration Tour as a dancer and featured guest.