During the Monday, Sept. 29 episode of Jay Shetty's On Purpose podcast, the seven-time Grammy winner recalled "sobbing" every night amid her months-long custody battle over her son Rocco. "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, 67, told the podcaster, 38. Rocco Ritchie, Madonna, Guy Ritchie and Lourdes Leon in January 2007 in London. Rocco Ritchie and Madonna in Paris. Madonna/InstagramIn December 2015, a judge ordered that Ritchie return Rocco to Madonna in New York; however, Rocco continued to live in England.