Inside Madonna and Son Rocco Ritchie's Relationship: How the Teen Went From His Mom's…

Rocco Ritchie‘s mom is based in the United States and his dad lives in London.

It’s not the most shocking thing ever to hear that Rocco, who turned 16 in August, wants to be living with his father at the moment. At such a pivotal age, where teenage angst finds you even if you don’t go looking for it, a boy could just need his father.

But if your mom is Madonna, the choice to live with Dad instead of Mum may sound like a bigger deal to those paying attention to the ups and downs of the “Vogue” artist’s personal life.

And since it took nine months for Madonna to hammer out an agreement with Rocco’s father, Guy Ritchie, who since divorcing the pop icon in 2008 has had three more children with wife Jacqui Ainsley, it started to sound as if more unusual issues were at play than your average “I want to live with Dad” conversation.

Rocco John Ritchie was born on Aug. 11, 2000, a few months before his parents got married at Scotland’s Skibo Castle. He joined big sister Lourdes Leon, Madonna’s daughter with Carlos Leon, in the family fold.

Rocco was born in Los Angeles, as Lourdes was, though the family was living mainly in London. Madonna had told an L.A. radio station just days before his birth that he would be born in the U.S., as she found English hospitals “old and Victorian.”

It was after Lourdes was born in 1996 that Madonna started studying Kabbalah; she didn’t talk that much about it publicly but she became a de facto celebrity face of the practice regardless thanks to her higher-than-most profile.

“You would think that studying the mystical interpretation of the Old Testament and trying to understand the secrets of the universe was a harmless thing to do,” she reflectively wrote in an essay for Harper’s Bazaar in 2013. “I wasn’t hurting anybody. Just going to class, taking notes in my spiral notebook, contemplating my future. I was actually trying to become a better person.”

But it was motherhood itself that marked the biggest turning point in the Material Girl’s life. In an excerpt of her diaries published by Vanity Fair after Lourdes arrived, she wrote, “I was stunned when I saw on the ultrasound a tiny, living creature, spinning around in my womb,” she wrote. “Tap-dancing, I think, waving its tiny arms around and trying to suck its thumb. I could have sworn I heard its laughing.”

Madonna, whose own mother died when she was 5, told Oprah Winfrey in what was a major talk show event at the time that she felt being a mom would “heal a lot of the pain I felt growing up without a mother.”

“All I can say is, when I look into my daughter’s eyes right now, I feel like, I feel that I’m being healed,” the singer said.

Rocco was born in 2000, and then in 2006 Madonna started the process of adopting her third child, son David Banda, from Malawi—the official paperwork took roughly two years, and just months after the adoption was finalized she and Ritchie split up.

In spring 2009 Madonna adopted daughter Mercy James, also from Malawi. She returned to the U.S. with the kids and started to lose the British vocal affect she had picked up over the previous 10 years.

…”Here I am, divorced and living in New York,” Madonna also wrote in Harper’s Bazaar in 2013. “I have been blessed with four amazing children. I try to teach them to think outside the box. To be daring. To choose to do things because they are the right thing to do, not because everybody else is doing them.”

Madonna was also out promoting the concert documentary Madonna: The MDNA Tour in 2013 and, while she didn’t spill too many details, she definitely sounded like the mom of a teen and a tween while chatting with Good Morning America.

“Ever since my daughter got an iPhone she stopped talking to me,” she joked, adding that Rocco, who was 12 at the time and just starting to grow facial hair, had yet to get his first mobile device. Madonna agreed with the assessment that she was a “pretty strict” mom.

But Rocco did get to dance on tour and take trips to Ellen and CNN, where he patiently waited for his mom to finish an interview with Anderson Cooperabout her Art for Freedom video project—which Madonna had called one of the most important things she’d ever done next to raising her kids.

“Obviously, I feel a great sense of responsibility being a good parent and raising my children,” she told Cooper. “I don’t take that job very lightly. Who they are, what they become and what they contribute to the world is very important to me. No slacking in that area, thank god, but the same goes with this film.”

“Is your mother strict?” Ellen DeGeneres asked then 12-year-old Rocco when he was invited to join them on Ellen for a turn in the splash tank (which is like a dunk tank, only the water falls on you from above if the thrower hits the target) benefiting Ellen for the Cure. “Is she a good mother?”

“Ummm, yeah. She’s a good mother. But, yeah, she’s…” the boy agreed.

“She’s what?” Madonna interjected.

“She’s a good mother, yes,” he smiled. “She’s very strict, but in a good way.”

Asked how he felt when Mom would flash herself on occasion in public, he shook his head good-naturedly in a “jeez” sort of way and, closing his eyes, said, “I actually don’t see that.”

The family celebrated Rocco’s 13th birthday on a yacht, where he popped and locked his way across the deck, much to his mom’s delight as she later shared the cute video on Instagram.

Responding to a question about rumors that she leaves day-to-day childcare to others, Madonna reiterated in March 2015 on The Howard Stern Show that she was a hands-on mom. “I do have help, but they don’t raise my kids,” she said. “They don’t teach them morals, you know, and they’re not as…they’re not stand-ins.”

“I do love [being a mother],” the artist said. “It’s also exhausting.”

About her kids’ reaction to her more provocative work, now that they’re old enough to be paying attention, she told Stern, referring to a couple of tunes on Rebel Heart, “They’re used to it by now. I mean, they do roll their eyes a little bit—actually, I think my son likes the beat of ‘Holy Water’…They like the music. They did roll their eyes a little bit about the lyrics, but they’re used to it. I’m their mom at this point. They separate it.”

Perhaps because Rocco spent his earliest years in the most nuclear-family of familial situations, with two parents sharing one roof (minus owning various roofs around the world and necessarily having to spend a certain amount of time apart because of their respective careers), Madonna hasn’t publicly talked about Rocco’s birth or upbringing as much as she did when Lourdes was born to much fanfare, or when she adopted David and Mercy, which of course ended up being controversial.

“It crushed me,” she admitted to Stern about all the backlash she got when she adopted, the drawn-out legal process and the privileged-celebrity aspect having dominated the headlines at the time. “I have to say, it was one of life’s great disappointments…It was really a bizarre experience.”

But throughout, Madonna and Rocco remained close, Mom showing off her son’s musicianship on social media and the young man often by his mother’s side, be it at home or while on tour. He danced on her MDNA Tour and hit the road with her again when she embarked on her 2015 Rebel Heart Tour.

“I think he’s probably gonna work behind the scenes,” she previewed the tour for Entertainment Weekly in August 2015. “He’s not interested in performing on stage with me right now. There’s way cooler things. Your mom is not that cool when you’re 14.”

Hindsight is 20/20, but something shifted in their relationship soon after that—or, most likely, a change in their dynamic was already underway.

In December 2015, Madonna headed to court in New York for custody-related matters and it was revealed that Rocco had been living in London with his father and wanted to continue to do so.

A judge ruled that if he wanted to relocate to London, he first had to return home to New York for them to legally be able to take the next step, but the teen remained abroad. Madonna spent Christmas with Lourdes, David and Mercy and posted a pic of herself with Rocco on Instagram, writing, “Merry X-mas to the Sun-shine of my Life.”

“Rocco spent most of the second half of 2015 on tour with his mother and got upset about not spending enough time with her,” a source told Page Six in January. “Even by her ruthless standards, Madonna has been particularly driven on the tour, and when Rocco did see her, he felt like she was trying to micromanage his life.”

It was rather obvious that Rocco wasn’t joking about his mom’s strictness during that Ellen appearance. Add to that the onset of adolescence and not getting to see his dad that much, not to mention the nature of his mother’s artistry (which, even if he used to take it in stride, might be weird for a 16-year-old)…

And while this sounds like a common development among children whose parents are divorced, a lot of fingers were pointed at Madonna as having caused the riff with her son because she was too focused on her work, to the detriment of her parenting.

“Its possible to be an entertainer and a good mother!!! Too bad we don’t live in a society where many encourage strong independent single working moms! The next great Frontier!” Madonna captioned a recent-but-still throwback picture of all of her four kids on Jan. 9.

A month later, a source told People that Rocco still wasn’t going to school in England, which concerned his mother a great deal. A date for progressing on the custody arrangement came and was postponed.

“Tu me manque,” or “I miss you,” Madonna captioned a baby pic of Rocco on Feb. 16.

On March 2, lawyers for both parties appeared in court in New York, where it was decided that Rocco would remain in London while Ritchie and Madonna continued to negotiate a revised custody deal. 

Madonna gave her son a shout-out in concert in Auckland, New Zealand, on March 5, dedicating “La Vie en Rose” to him and telling the crowd, “There’s no love stronger than a mother for her son, and if I talk about him too much, I’m going to cry.” 

Rumors started to fly that the custody battle was taking its toll on Madonna, whose Rebel Heart Tour wrapped March 20 in Sydney.

She screengrabbed a fan’s post defending her artistry and professionalism, and captioned it: “Thanks for supporting me. Too bad people don’t know the art of acting and playing a character. I could never do any of my shows high or drunk. And yes underlying all of this is sexism and mysongony [sic] which proves that not only do we not get equal pay bUt we are still treated like heretics if we step out of line and think outside the box! . Sexism is alive and kicking but i am… #livingforlove.”

Ultimately Rocco was allowed to stay in London through the summer and Madonna and Ritchie quietly settled things in September. The terms of the agreement were, of course, confidential, but Madonna and Rocco have not had any public reunion since.

A few weeks after the court drama ended, Rocco was reportedly arrested on Sept. 28 in north London for possessing cannabis. News of his weed bust didn’t get out until last week, in response to which Madonna said in a statement, “I love my son very much. I will do whatever I can to give him the support that he needs, and I ask that you respect our privacy at this time.”

“Reasons to be thankful!!” Madonna wrote on Thanksgiving last week alongside a photo collage of Lourdes, Rocco, Mercy and David. She also unintentionally set off a little debate among fans and critics in the comments section, with those defending the pop star opining that mother and son were just going through a phase.

“People give her a break… my son is very similar in his rebellious ways,” wrote @nsp4772. “Challenging and difficult but we are mothers doing what we can to support our children through their journey. We may know see and tell them from experience that they shouldn’t be taking risks but they do anyway! Life is hard so stop bagging out the family unit! Individual personalities are simply that! Good luck Madonna things will work out with your continued guidance and support. Love will conquer!”