Madonna, nearly 68, is on track to take the No. 1 album on Billboard this week, beating Gen Z hitmakers Olivia Rodrigo and Ella Langley by an elbow.
And she did just that by getting more personal than ever with the lyrics of “Confessions on a Dancefloor Part II.” The song is believed to be about her late brother, stepmother, and ex-husband Sean Penn, whom Madonna sings about having “blackmailed” her.
A friend of Madonna’s told Page Six that the incident was a “surprise” but that the actor remains “the love of her life.”
Madonna recently said she approached the superstar about writing songs together “as a way to repair our relationship,” including duets and co-writing songs with her 29-year-old daughter Laura (née Lourdes) Leon.
“There were moments where Madonna and Laura didn’t speak,” a friend of Madonna’s told Page Six. “Laura always felt that Madonna was quite hard on her growing up, and unnecessarily so.”
Madonna, on the other hand, also felt guilty for raising Laura to a world of unimaginable fame and how it affected her life.
In the song, Madonna calls her daughter “Little Star,” the same affectionate name she called her daughter on her 1998 album Ray of Light, when Laura was two years old.
“You didn’t ask for all the flashing lights/I didn’t think about how confusing it would be/or how it would hurt/I wish I knew/I didn’t think about the pain I caused,” she sings.
“She understands how a child of someone so famous would struggle with their identity, and she feels guilty about that,” said a friend. “One of the reasons why we distanced ourselves was because Laura didn’t want to be seen as Nepo’s baby.”
Lola was born to Madonna and fitness trainer Carlos Leon. Carlos Leon dated Madonna from 1994 to 1997 after they met while she was jogging and he cycling in Central Park. Stories have been circulating for years about how strict the naturally free-spirited singer is with her six children, including sons Rocco Ritchie, 25, and David Banda, 20, whom she adopted with ex-husband, director Guy Ritchie, and adopted daughters Mercy James, 20, and Stella and Estelle, both 13.
She keeps her children on a macrobiotic diet, with no sweets, dairy or preservatives, and is said to be banned from television. Page Six previously reported that Laura didn’t get an iPhone until she turned 15 and that if her clothes were left on the floor, the items would be taken away.
“I think my mom looked at all the celebrity kids and thought, ‘My kids aren’t going to turn out like this…'” Laura told Interview magazine. “My mother is very uncontrollable and has always controlled my life. I needed complete independence from her as soon as I graduated from high school.”
That meant the girl, who grew up between London and Manhattan, graduated from LaGuardia High School and dated Timothée Chalamet before he became famous, then moved to Bushwick, Brooklyn, to try to start her own music career. She recently dated photographer and skateboarder Jonathan Puglia, but is currently single.
As Lola Hole, she released a few dance-pop singles in 2022 and 2023, but has not released any more singles recently.
“Madonna always knew Laura didn’t want anything to do with her mother when it came to music, so she was really touched when Laura suggested it,” the friend said. “Madonna and Lola have been in so much pain that sometimes it’s hard for them to be who they are, but working on this song together worked really well.”
Page Six reports that the singer, who has been active for 60 years, was in a nostalgic mood when he wrote the album. Madonna likes to be seen as ageless, but in 2023 she experienced a life-or-death scare when a bacterial infection led to sepsis and left her in a coma for four days.
For the past few years, she has been writing a script about her life, and after a grueling audition process, actress Julia Garner was cast in the lead role. However, production was canceled due to reported budget discrepancies with Universal Pictures.
Madonna then attempted to turn her life story into a series, working on a script for Netflix. When that stalled as she struggled to find a suitable showrunner, she decided to put her memories to use in a new creative project.
The singer collaborated with producer Stuart Price on her 2005 album Confession on a Dance Floor, which included her hit song “Hang Up” and was a fan favorite. In 2024, she visited Price’s home in London to see if 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 said in an interview, “A lot of the songs on here are confessional. I feel like my brain is tuned to memory and how it’s connected and where it’s taken me. The past is a very important part of my life. It’s not something I cling to, but something I learn from and share with others.”
She sings in “Fragile”: “When I’m alone/I see you standing there/I see inside your soul/And I feel complete.” This is believed to be about Christopher, who was once her closest ally and confidant and also worked with her as a choreographer and dancer. However, the two had a falling out, with Christopher calling Penn “intense”, Carlos Leon “brazen” and Guy Ritchie a “poster” in a 2008 book, and Christopher said he held a grudge against his sister.
“I hadn’t talked to him in years and years,” Madonna told podcaster Jay Shetty in 2025. It was like that. ”
Similarly, she had a volatile relationship with Joan, a woman who married Madonna’s widowed father, Tony Ciccone, when she was only eight years old. “When I was young, I couldn’t accept my stepmother,” she once told Larry King.
Joanne died after being diagnosed with an aggressive form of cancer. In the song “Betrayal,” Madonna sings: “When the book of love is written, I’m the writer/And by the last page your name won’t be mentioned…You’ll never take my mother’s place.”
And there’s also a pen. Penn said their marriage was rocky from 1985 to 1989, including several scuffles with paparazzi and long-denied rumors that he tied her up and held her hostage, which led to a SWAT team raiding his home.
She drops clues that the song “Bizarre” is about him. The lyrics, “Movie star, deep blue eyes/In Hollywood, we’re the perfect prize/He drove too fast/Shelby Cobra, it wasn’t supposed to last,” allude to the sports car that was said to have been a gift to Penn on their wedding.
“She considers Sean the love of her life and is happy to express that publicly,” a friend said.
For the past two years, she has been dating soccer player and coach Hakeem Morris, 30, but neither of them are considering marriage, the friend added.
“She knows that Akeem may want to have children someday and is not considering adopting any 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 plans to live there for at least a few more years. That means she gets to see more of Rocco, her son with Richie, and they’re also closer than ever.
In 2015, when Rocco was 15 years old, he refused to leave his father’s house in London to spend the holidays with his mother in New York City, leading to a custody battle in court. Last fall, Madonna revealed on Shetty’s On Purpose podcast that at the time, “I was actually contemplating suicide. I know this sounds really weird since I’m not an emo guy, but I just thought, ‘I can’t take this pain anymore.'”
“Like Lola, Rocco is independent,” says a friend of Madonna’s, a young artist who paints under the name Red. “When he was a kid, he used to berate Madonna about how hard she was on him, but she wanted the best for her kids. She didn’t want them to go down the Hollywood path of doing nothing and falling into drugs.” And I think she did a good job.
“Rocco now understands what he was trying to do.”
Next, Madonna is reportedly planning a concert tour, but friends and family admit they are worried about how hard she worked last time and that it contributed to her illness, and hope she doesn’t do so.
Like many other singers who Social Security officially considers to be of “full retirement age,” the singer suffers from knee pain. Because the cartilage in her left leg is gone, she has had to refrain from dancing. Instead, she rides her bike incognito in London’s parks and keeps fit on the Peloton.
“Mentally she’s completely fit, but just hoping her body will keep up,” the friend said. “But she loves the response to the album. She sees what she’s done as a survivor’s story. And it’s incredible how long she’s survived at the top of the music industry. Right at the top.”
