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. “Now he’s taking risks. He reminds me on a regular basis that he’s essentially invested all this money in the crypto world.” (Amusingly, their close bond didn’t guarantee Madonna the NFT ape she wanted from the Oseary-repped Bored Ape Yacht Club. )
As Oseary settled down, started a family, and rose in prominence as a manager, producer and investor, Madonna has learned, somewhat begrudgingly, to share her dear friend. “I’m not happy sharing him with apes. Cryptocurrency, Ethereum, U2, Anthony Kiedis, his four children and wife,” she jokes. “Why did all these people have to show up?”
Read on for more from the endlessly quotable multi-hyphenate.
How has Guy evolved over the years?
He’s changed a lot since I met him. When I met Guy, he was 18 years old. My first reaction to him was that he had a lot of opinions. But then, as I got to know him, I realized that he had good taste in music and recognized talent. We just became friends. I would get his advice about people I was dating and he was always going after supermodels that were breaking his heart.
In business, was he good cop to your bad cop?
More or less. I was always the adventurous, crazy one. 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. But that didn’t happen right away. We were on even ground and then, as the years went by, he took on a more of a parental role. He was always very practical. When I would go on tour, he would try to get me to do less production because then I would have less overhead and make more money. He was always the voice of reason and I was the mischievous one pushing the envelope.
Guy says that your risk taking rubbed off on him as a businessman.
He’s always been the man behind the artist taking the risk. Now he’s taking risks. He reminds me on a regular basis that he’s essentially invested all this money in the crypto world.
Which brings us to Bored Ape #3756.
I was so pissed off that I didn’t get the one I wanted. Once I get my mind around something then that’s what I’m going to have. But I learned quickly that wanting 32 musicians on stage in a small theater is not the same as wanting an ape with a leather motorcycle cap and multicolored teeth.
That’s the one you wanted?
Yeah and I didn’t get it. Even though I was told that it was inspired by me, and modeled after me. It was bought by a woman who is a fan of mine. I was like, “She should just sell it to me!” She was gonna sell it to me, but it was way, way too expensive. I can’t afford my own ape.
Do you share everything with Guy?
To a point. Once he got married, he created his own universe. Obviously, I had him all to myself and now I have to share him with his wife, which really pisses me off. I’m kidding! Before that a lot of pretty girls came and went — he’s gonna kill me for saying all of this — but then he settled down with a really nice girl. I was like, “God dammit. Now I have competition!” And then he started managing other artists, which really pushed me over the edge.
You have an unconventional relationship.
Like I said, before it was just me and Guy. We did everything together. I remember the tour where he went, “I can’t do this anymore.” It was for MDNA. I never settled down in a conventional way. I have a very unconventional family. I call myself a citizen of the world and my family unit moves with me.
He couldn’t be on the road all the time?
It probably had to do with him wanting to grow a business, but also having a family. Now he’s the old man in the house in Benedict Canyon. Is that where he lives? One of those canyons. I’ve only been to his house 3,000 times. But he has a lot of practical, calm wisdom that I do not have, so we still have a good dynamic. It’s just shifted.
What are your plans for music going forward?
I’m just looking for interesting, fun ways to rerelease my catalog and introduce my music to a new generation. I’m focused on that and I’ve been writing a screenplay for my film for the last couple of years. The whole thing with “Frozen” was so fun, but I woke up one day and went, “I’m sick of living in the past!” I want to go on tour again, I’m a creature of the stage. That is my happy place.
Would you miss Guy on tour?
I’m always happy to see him. In my opinion, he doesn’t come around enough. I wish he would come around more. I’m not happy sharing him with apes. crypto currency, Ethereum, U2, Anthony Kiedis, his four children and wife. Why did all these people have to show up?
Guy says you shot down any consideration of selling your song catalog. Why?
Because they’re my songs. Ownership is everything isn’t it? I mean, that’s why he’s buying apes.
Where are you at with the biopic?
I have a very long script that is really hard for me to make shorter. I’ve been whittling away at it, but it’s like hacking off my limbs.
Why did you decide to make the film?
I’ve had an extraordinary life, I must make an extraordinary film. It was also a preemptive strike because a lot of people were trying to make movies about me. Mostly misogynistic men. So I put my foot in the door and said, “No one’s going to tell my story, but me.”
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