Madonna on ‘Ride or Die’ Guy Oseary, the Bored Ape That Got Away and Her Upcoming Biopic: ‘No One’s Going to Tell My Story but Me’

variety.com:

Madonna became close with the man she calls her “ride or die” in the same way that most people bond: through late nights out, long conversations — and no small amount of mischief.In an interview with Variety, the pop icon opens up about her unconventional relationship with Variety’s 2022 Music Mogul of the Year Guy Oseary, that extends from partner-in-crime, at least in their early days in Miami, to trusted business partner and source of “calm wisdom.”“I was always the adventurous, crazy one,” Madonna says. “As soon as Guy would get a little look of fear in his eyes, I’d think it was a good idea.

I would use him as a weathervane.” However, that dynamic only crystallized over time. When the hitmaker first met Oseary, just 18 at the time, they were both unapologetic troublemakers. “As the years went by, he took on a more of a parental role,” Madonna reveals.

Oseary urged the notorious workaholic to rest more and spend wisely. Occasionally, Madonna heeded his advice. More often than not, she remained unswayed — such as the time Oseary suggested the superstar tone down on the elaborate staging of her tours. “He would try to get me to do less production because then I would have less overhead and make more money,” Madonna says. “He was always the voice of reason.”While Oseary is now “the old man in the house in Benedict Canyon” according to his most famous charge, Madonna’s fearlessness has rubbed off on him in perhaps unexpected ways.

Like his forays into the world of cryptocurrency and NFTs. “He’s always been the man behind the artist taking the risk,” she says.