What's more iconic in art than Madonna and child? And when the earthly artist became a mom in 1996 at the age of 38, it was a major pop culture event. The "Like a Virgin" singer wasn't exactly a single parent, sharing daughter Lourdes Leon with Carlos Leon , her trainer-actor partner at the time. But Madonna made it clear she would be doing motherhood her way.

"He knew what he was getting into when he rang my doorbell," Madonna quipped to Oprah Winfrey of Carlos in December 1996 when she sat down for what was not only her first interview since giving birth, but her first- ever on-camera interview that lasted longer than 12 minutes (as the host of Oprah excitedly announced to her audience). That eff-your-judgment vibe has been the story ever since for the now 66-year-old Material Girl , who's also mom to Rocco Ritchie , 24, David Banda , 18, Mercy James , 18, and twins Stella and Estere , 11. And if you think fans of the boundary-pushing Truth or Dare star were surprised in the 1990s to see her taking a turn for the settled-down, you can count Madonna herself among those who at one point didn't envision having any kids, let alone a big family of her own.

Just 5 years old when her own mom (also Madonna Louise Ciccone ) died, "I rejected the idea of being a mother well into my 30s because I associated motherhood with sacrifice suffering and ultimately death and I wanted none of that," the Michigan native wrote in a 2023 Mother's Day post . "I decided to rip the a--hole out of li.