Madonna Didn't Always Have The Best Relationship With Her Son Rocco

American (though sometimes British-sounding) pop star Madonna is undoubtably known as one of the foremost musical icons of the 20th and 21st centuries. Throughout the years, the singer has scored seven Grammy Awards from 28 nominations, and has sold over 300 million records – making her one of the best-selling musical artists of all time. Nonetheless, Madonna has also had her fair share of controversies, many of which have surrounded her personal life, including her two husbands (and two divorces), many relationships, and six children. 

Naturally, despite her nearly deistic status, Madonna is still human, and as a result has experienced a lot which has missed the headlines. One interesting aspect of her personal life involves her relationship with her son Rocco Ritchie, to whom she gave birth in 2000. It turns out that, despite the endless adoration Madonna may have received from the public over the last four decades, her relationship with her own family — including her eldest son — is a bit more rocky. 

News surrounding Rocco Ritchie, Madonna's son with Guy Ritchie, arguably broke through in September 2015 when he became the subject of a noteworthy custody battle between his parents. The dispute began because Rocco wanted to remain with his father in England, while Madonna wanted him to return to New York, per BBC News. Rocco's lawyer told the court, "Having this order over his head is stressful and upsetting to him." Understandable, considering he was only 15 at the time. Madonna later dropped the custody application and decided to settle the dispute outside of court. 

In the end, per the Daily Star, Rocco ended up staying with his father in London while Madonna spent Christmas with her other three children in New York. Madonna and Rocco ended up reuniting the following year, when Rocco was 16, upon Madonna's return to the U.K. 

Now that the custody battle has been settled, Madonna and her son appear to have a healthy relationship. In fact, Rocco is frequently the subject of his mother's social media posts. One, for instance, celebrated Rocco's 22nd birthday in August; another in December 2021 consisted of Madonna proudly sharing artistic photoshoots of him in homage to actor James Dean.

Rocco Ritchie may have had a turbulent relationship with his mother for a while before 2015, perhaps beginning when he first went on tour with her as a dancer at the age of 11. A few months into the tour, Rocco appeared on "Ellen" with Madonna, where the host pressed him about his relationship with his mother. 

"Is your mother strict?" Ellen asked the then-12-year-old. "Is she a good mother?" After some hesitation, Rocco responded, "Yeah, she's a good mother. But ... yeah." When Madonna jokingly pressed him on this, he repeated that she was a good parent, adding, "She's very strict, but in a good way." 

Rocco is not Madonna's only child to refer to her as strict. In 2021, his elder sister Lourdes Leon, Madonna's daughter by fitness trainer Carlos Leon, told Interview magazine that despite her mother's exorbitant wealth, she had to pay for everything herself, including her college tuition and rent. "We don't get any handouts in my family," Leon said. "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.'" Leon added that this agreement was partly her decision too, as her mother is "such a control freak" who has "controlled me my whole life." As a result, she felt the need to become "completely independent" from her as soon as she graduated high school, which included financial independence.