At almost 68, Madonna is on the verge of overtaking Gen-Z sensations Olivia Rodrigo and Ella Langley to claim the top spot on the Billboard album charts this coming week.
She has achieved this milestone with her latest album, “Confessions on a Dance Floor Part II,” which features some of her most personal lyrics to date. The songs are said to touch on her late brother, stepmother, and her former husband Sean Penn, who Madonna claims felt “threatened by” her.
A close friend of Madonna revealed to Page Six that, although one track about Sean Penn may come as a surprise, he remains “the love of her life.”
Additionally, the album includes a duet co-written and performed with her 29-year-old daughter, Lola (born Lourdes) Leon. Madonna recently mentioned that Lola suggested they create a song together “as a way to heal our relationship.”
A source close to Madonna confided to Page Six, “There were times when Madonna and Lola weren’t on speaking terms. Lola often felt that her mother was overly strict during her upbringing, perhaps more than necessary.”
Madonna, meanwhile, “also felt guilty about bringing Lola up in a world of unimaginable fame and about how that had an impact on her life.
In the song, Madonna calls her daughter “little star” — the same affectionate name she called her by on her “Ray of Light” album in 1998, when Lola was two years old.
“You didn’t ask for all the flashing lights/ I didn’t think of how it could disturb/ Or how it hurt/ I wish I knew/ The pain I’ve caused,” she sings.
“She understands how a child of someone so famous would struggle with their own identity, and she has felt guilty about that,” the friend said. “The distance came partly because Lola didn’t want to be seen as a nepo baby.”
Lola was born to Madonna and Carlos Leon, a fitness trainer the singer dated from 1994 to 1997 after meeting while she was jogging and he was biking in Central Park. Stories have circulated for years about how strict the otherwise libertine singer is with her six children (including sons Rocco Ritchie, 25, and David Banda, 20, whom she adopted with ex-husband and film director Guy Ritchie; and adopted daughters Mercy James, 20, and Stella and Estere, both 13).
She’s been said to keep them on a macrobiotic diet — no sweets, dairy, or preservatives — and TV is banned. Page Six previously reported that Lola got an iPhone only after turning 15 and that if any of their clothing was left on the floor, the items would be taken away.
“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 … ‘ ” Lola told Interview magazine. “My mom is such a control freak, and she has controlled me my whole life. I needed to be completely independent from her as soon as I graduated high school.”
That meant moving to Bushwick, Brooklyn, after growing up between London and Manhattan — where she graduated from LaGuardia High School and dated a pre-fame Timothée Chalamet — and trying to start her own music career. She was more recently involved with Jonathan Puglia, a photographer and skateboarder, but is said to be single now.
As Lolahol, she released a handful of dance-pop singles in 2022 and 2023, but nothing more recently.
“Madonna always felt that Lola didn’t want to be associated with her mother when it came to music, so she was really touched when Lola suggested it,” the friend said. “Madonna and Lola have sometimes struggled to just be, as there is quite a lot of pain there, but they are doing really well thanks to creating this song together.”
Page Six is told that the singer, who has been performing for six decades now, was in a nostalgic mood when she wrote the album. While Madonna would like to be seen as ageless, she also had a life-or-death scare in 2023 with a bacterial infection that led to sepsis and left her in a coma for four days.
For the last few years, she had been working on a script about her life, with actress Julia Garner set to play the star after a grueling audition process. But the production was scrapped amid a reported budget disagreement with Universal Pictures.
Madonna then attempted to turn her life story into a series, working on a script for Netflix. When that stalled over struggles to find the right showrunner, she decided to use her memories for a new creative project.
The singer had worked with producer Stuart Price on the 2005 album “Confessions on a Dance Floor,” a fan favorite that included her hit song “Hung Up.” In 2024, she visited Price’s home in London to see whether the old magic was there. At the time, her brother Christopher Ciccone was dying of pancreatic cancer and her stepmother, Joan Clare, had just passed away.
Madonna recently told Interview that “a lot of the songs here are confessional. I feel like my brain is tuned into memory and how it’s all connected and where it has brought me. The past is such an important part of my life — not to dwell in, but to learn from and share with other people.”
She sings on “Fragile”: “When I’m alone/ I see you standing there/ I see inside your soul/And I feel whole.” It is believed to be about Christopher, who had once been her closest ally and confidant, even working with her as a choreographer and dancer. But the two had fallen out — with Christopher saying his sister held grudges — in part over his 2008 book, in which he called Penn “intense,” Carlos Leon “thick” and Guy Ritchie “a poser.”
“I didn’t speak to him for years, years and years,” Madonna told podcaster Jay Shetty in 2025. “It was him being ill and reaching out to me and saying, ‘I need your help,’ and me having that moment like, ‘Am I going to help my enemy?’ That’s how it felt.”
Likewise, she had a rocky relationship with Joan, the woman who married Madonna’s widowed father, Tony Ciccone, when the singer was just eight years old. “I didn’t accept my stepmother when I was growing up,” she once told Larry King.
Joan died after being diagnosed with an aggressive form of cancer. In the song “Betrayal,” Madonna sings: “When the book of love is written, I am the writer/ And by the last page, you will not be mentioned … You’ll never take my mother’s place.”
And then there is Penn. The two had a turbulent marriage from 1985 to 1989, including the actor’s several scuffles with paparazzi and long-denied rumors that he had tied up her and held her hostage — leading to a SWAT team storming his house, according to Penn.
She drops clues that the song “Bizarre” is about him — “Movie star, deep blue eyes/ In Hollywood, we’re a perfect prize/ He drove way too fast/ Shelby Cobra, wasn’t meant to last” alludes to a sports car she was reportedly gifted Penn when they wed.
“She sees Sean as the love of her life, and she is happy to put that out there,” the friend said.
For the past two years, she has been involved with soccer player and coach Akeem Morris, 30, but the friend added that neither is thinking about marriage.
“She knows Akeem might want to have kids one day, and she’s ruled out adopting more, so she knows there may be a time limit,” the friend said.
These days, she is primarily based in London — where she once lived with ex-husband Guy Ritchie — and has said she will be there for a few more years at least. It means she gets to see more of Rocco, her son with Ritchie, and they, too, are getting on better than ever.
In 2015, when Rocco was 15 years old, he refused to leave his father’s home in London to spend the holidays in New York City with his mother, leading to a courtroom custody battle. Last fall, Madonna revealed on Shetty’s “On Purpose” podcast that, during that time, “I actually contemplated suicide. That probably sounds really weird coming from me because I’m not emo … but I was like, ‘I can’t take this pain anymore.’”
“Like Lola, Rocco is independent,’ says Madonna’s friend of the young artist, who paints under the name Rhed. “He also used to rail at how tough Madonna was on him when he was growing up but she was trying to do her best for her children — she didn’t want them to go down the Hollywood route of doing nothing and falling into drugs. And I think she did a good job.
‘Rocco now understands what she was trying to do.”
Up next, Madonna is reportedly making plans for a concert tour — although friends and family, concerned about how hard she worked herself last time, which helped lead to her illness, have admitted they hope she doesn’t.
Like many others who are officially what Social Security considers “full retirement age,” the singer is suffering from a bad knee. The cartilage in her left leg has gone, and it has meant that she has to curb her dancing: instead, she keeps fit on a Peloton while also biking incognito in London’s parks.
“Mentally, she is totally on the ball, but she just wishes that her body would keep up,” said her friend. “But she has absolutely loved the response to the album. She sees what she’s done as the story of a survivor, and it’s incredible how long she has survived at the top of the music business. The very top.
