Madonna is reflecting on a difficult time in her life.
Nearly 10 years after her highly publicized custody battle with ex Guy Ritchie over their now 25-year-old son Rocco, the “Hung Up” singer admitted it is still one of the most excruciating memories to look back on.
“Probably one of the most painful moments in my life where I honestly couldn’t see the forest through the trees was when I went through a custody battle with my son,” Madonna explained during the Sept. 29 episode of On Purpose with Jay Shetty. “Someone trying to take my child away from me, it was like you might as well just kill me. That’s really how I was thinking.”
Indeed, the 67-year-old admitted that the custody battle, which began when her then-teenage son left her Rebel Heart tour to stay with his father in London in 2015, was more painful than her 2008 divorce from the Snatch director.
“A lot of people’s marriages don’t work out,” Madonna explained. “They marry the wrong people. They’re not aligned, they’re not meant for each other.”
And for the seven-time Grammy winner—also mom to Lourdes Leon, 28, with Carlos Leon, and adopted children David, 20, Mercy, 19, and twins Stella and Estere, 13—it was even more painful to carry on her 82-date tour amid the legal back-and-forth with Ritchie.
“I had to go on stage every night,” she recalled. “I would just be lying on the floor of my dressing room, sobbing. I really thought it was the end of the world. I couldn’t take it.”
The legal case began in December 2015, when Rocco, then 15, abruptly left his mother’s care as she toured, opting to stay with his father in London. Madonna and Ritchie, who were married for eight years, subsequently spent several months battling in court, ultimately settling in June 2016, E! News learned at the time, with Rocco returning to New York.
“Thank God I don’t feel that anymore,” Madonna added of the six-month period during her On Purpose appearance. “At the end of the day, I needed to learn some lessons.”
Despite her fractured relationship with Rocco at the time, the mother-son duo were able to grow together. As the “Material Girl” singer noted, “I’m now really good friends with my son.”
For a deeper look into Madonna’s family, keep reading…
Lourdes Leon
Madonna met Carlos Leon while on a jog in Central Park in September 1995 and fell fast for the Cuban American personal trainer turned actor.
Production on Evita—a role Madonna fought tooth and nail to play—had just gotten underway the following year when she got pregnant.
"This is not exactly how I envisioned starting a family," she told Vanity Fair in April 1996.
But she was referring to her intense filming schedule, not the fact that she and the baby's father weren't married, or whatever social mores dictated at the time.
"Some people have suggested that I have done this for shock value," Madonna said. "These are comments only a man would make. It's much too difficult to be pregnant and bring a child into this world to do it for whimsical or provocative reasons. There are also speculations that I used the father as a stud service."
Having been married to Sean Penn from 1985 to 1989, she expressed no interest in retying the knot.
"I believe that most people would be more comfortable if I got married and the marriage failed," Madonna said. "I believe that divorce is more socially acceptable than single motherhood."
She gave birth to daughter Lourdes Leon on Oct. 14, 1996 (and won a Golden Globe for best actress in a musical or comedy a few months later).
Madonna and Leon did break up in the fall of 1997, but they made co-parenting work.
"He is ever present in Lola's life and we are friends," Madonna told Vanity Fair in 1998, using her daughter's nickname. "And I'm very happy. It took a while for us to get to this place."
As for being a mom, Madonna said, "I knew that having a child would be an incredible healing experience...because I didn't have a mother. I just knew my karma was to have a girl, and I instinctively had a longing for her. But I didn't know what it was going to be like."
Lourdes enjoyed a few breaks courtesy of her mom—pulling flower girl-inspired performance duty at the 2003 MTV VMAs, singing backup on "Superstar" off of 2012's MDNA—but has also made her own career as a model and singer, performing as Lolahol.
After attending a performing arts high school in New York (where classmate Timothée Chalamet was a boyfriend), Lourdes paid her own college tuition, starting at Univerity of Michigan and graduating from NYC's Purchase College.
"We don't get any handouts in my family," she told her mom's BFF Debi Mazar for Interview in 2021. "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.'"
On making her own way, she told The Cut in 2022, "I want to feel like I deserve things and not just like I've been given things...Nepotism babies are pretty awful usually, and my mom and my father raised me to be so much smarter than that."
Rocco Ritchie
Madonna's British era began in 1998 when she started dating filmmaker Guy Ritchie.
The singer had told VF earlier that year that she would love to have another child, "but I'd like to be in a stable relationship. Sometimes you want to look over at somebody and say, 'What do you think we should do?'"
She and Guy welcomed son Rocco John Ritchie—named after one of Madonna's Italian uncles and Guy's father—on Aug. 11, 2000.
Madonna came back around to the idea of marriage a few months later, swapping vows with Guy in Scotland on Dec. 22, the day after Rocco was baptized.
After Madonna and Guy divorced in 2008, they shared custody of Rocco, who frequently hit the road with his mom when she was on tour.
He "threw himself" in front of her to get in on the act, Madonna said on Good Morning America in 2013, noting that Rocco had grown "a foot taller" in a year and, still shy of 13, was busy "looking at girls' butts."
She added appreciatively, "He's the showboat in the family."
Joining Madonna for an appearance on Ellen in 2012, Rocco called her "a good mother" who was "very strict, but in a good way."
A few years later, however, Madonna and Guy reworked their custody arrangement to allow Rocco more time in London with his father (who shares three other children with wife Jacqui Ainsley).
All grown up now, Rocco is a full-time artist and cofounder of the London gallery Maison Rhed.
"Moving to London had a huge effect on me," the Royal Drawing School alum told Vogue Hong Kong in 2022. "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. I was fortunate enough to know what I wanted to do at a young age and once I had settled into art school, it kick-started my work."
Before announcing his presence on the art scene, Rocco spent several years painting and showing his work under the moniker Rhed.
"It’s not that I don’t feel proud to be who I am," he explained. "On the contrary, I couldn't be prouder of my parents and what they've achieved and in turn taught me. I just needed enough time to develop and experience my own lessons just like they did, without the extreme public judgement."
Rocco met girlfriend Olivia Monjardin—his date to the March 2024 U.K. premiere of his dad's Netflix show The Gentlemen—while studying art at Central Saint Martins in London.
David Banda
In October 2006, Madonna adopted David Banda (born Sept. 26, 2005) from the Home of Hope orphanage in Lilongwe, Malawi.
Which, much to her surprise, caused quite the commotion, with critics alleging she practically stole a child who had a family.
"When I had my daughter, people accused me that I did it as a publicity stunt," Madonna told NBC News in an interview at the time. "I expected that. I didn't expect to be accused of kidnapping, or of doing something illegal. I didn't expect to be demonized."
In the meantime, however, David was doing great. "He's got a terrible temper," the singer said. "He's very flirtatious. And he's hysterically funny. Obviously he’s going to come with his own baggage and his own DNA and I look forward to being surprised by what he's going to offer the world and how he's going to turn out."
(In a statement to the BBC, David's biological father, Yohane Banda, whose wife had died from childbirth complications, said he was "very happy" David had been adopted, "because as you can see there is poverty in this village and I know he will be very well looked after in America.")
Paying tribute to David, an accomplished guitar player, on his 18th birthday in 2023, Madonna wrote, "It is impossible to believe that almost 18 years have gone by since We met you in Mchinji at Home of Hope Orphanage! Your name means 'Speak the truth'! I couldn’t think of a better name for an artist! You are growing into a truly remarkable human being! We are all so proud or you!"
Meanwhile, though they put up a united front while going through the adoption process with David, Madonna and Guy had split up by the time she was inducted into the Rock and Roll Hall of Fame in March 2008.
"We no longer have the idealistic expectation of a relationship," she told a German magazine at the time. "I gave up the dream that he is the perfect husband. He gave up the expectation that I am the ideal wife."
Mercy James
Unfazed by her first experience, Madonna returned to Malawi to adopt daughter Mercy James—born Jan. 22, 2006—in 2009.
And she was put through her paces yet again.
Officials who opposed the adoption cited her recent divorce as a reason why the singer was "not capable of raising a child," Madonna told People in 2017, recalling how her case went all the way to Malawi's Supreme Court before she could bring Mercy home. "The way I was treated— that sexist behavior—was ridiculous."
But Madonna made sure that her children maintained a connection to their home country, taking them back for visits and launching the charity Raising Malawi.
"Beautiful Mercy James," Madonna wrote when the budding musician and gymnast turned 18 in 2024. "You’re already a young woman! Beautiful African Queen!! You Surprised all of us!"
Estere and Stella
After meeting them at the same orphanage where she found David, Madonna adopted 4-year-old twins Estere and Stella (both names mean "star") from Malawi in February 2017.
"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," she told People. "I thought, 'What am I waiting for? Just do it.'"
This time, she admittedly made it a group decision, consulting her four older kids about expanding their family.
"Mercy and David were excited," Madonna recalled. For Lourdes and Rocco, it may have been "not jealousy," she added, "but an adjustment. Eventually everyone was supportive. Lola said, 'Mom, if that's what you want and it's going to make you happy, let's go.'"
Madonna's 6 Kids
Reflecting on her dynamic with her siblings, Lourdes said in 2022 that she only argued with her brothers.
"They’re just little a--holes sometimes," she told Debi for Interview. "A 15- or 20-year-old brother? Come on. Obviously we’re going to fight. But Mercy and I have never, ever fought about anything. She's always had my back and I've always tried to be the best big sister I can be for her. It's harder with the twins, because I don't live at the house anymore."
Madonna has said she's "blessed" that her children all have artistic passions.
"Starting from the top with Lola, who was not only an incredible ballet dancer and and a rhythmic gymnast, switching to musical theater and contemporary dance," she told fan blog Madonna-Infinity. "Now she is a unique singer and songwriter in her own right. When I go on tour, nothing brings me more happiness to know, we are all working on the same show creating the magic together."
"Of course," she added, "I am also their mother so sometimes we get on each other's nerves. We are a family of artists but are also a family and that’s what happens."
To Madonna it made "perfect sense" to include all the kids still living under her roof in her retrospective The Celebration Tour.
"David has played guitar since he was a child," she explained. "Mercy has played piano since she was 8 and has been classically trained most of her life. Eventually, when I adopted the twins, they started to play piano and dance as well....And then we add to that deejaying as Estere showed a keen interest in learning."
Stella was the shyest, Madonna noted, but she "comes alive on stage." The child is also "an incredible fine artist," she added, "and I’m hoping that she follows in the footsteps of Rocco, who after being a B-boy, skater, and graffiti artist has really come into his own as an incredible painter."