Guy Oseary

There is a version of Maverick Records that doesn't sign Alanis Morissette. That version has a different A&R exec - someone cautious, someone institutional, someone who'd already learned what the market wanted and was content to give it exactly that. That exec doesn't sign the album that becomes the cultural earthquake of 1995. Guy Oseary did, because he was 22 and didn't know he wasn't supposed to.

He'd arrived at Maverick in 1992, one of its earliest employees, at 19. Madonna had co-founded the label the year before. The idea was autonomy - an artist-run imprint that could take risks the majors couldn't. Oseary was the right person for the room. He didn't need prestige; he needed access and latitude. He got both.

He rose through the ranks to become Chairman - the youngest in the company's history. Under his watch, Maverick signed a roster that reads like a music school curriculum: The Prodigy, Muse, Deftones, Paul Oakenfold. He executive produced film soundtracks for The Matrix, Kill Bill, and the Austin Powers franchise. He also signed on as executive producer for all five Twilight Saga films and NBC's Last Call with Carson Daly.

But the most important thing he learned at Maverick wasn't A&R. It was how to run alongside someone at the absolute front of culture - and not flinch. That's the Madonna education. She doesn't slow down for consensus. She doesn't look back. "One of the things I've learned working with Madonna," Oseary has said, "is you just move forward. It's really rare that she ever brings up the past." It's a management philosophy that has served him across industries.

When Oseary became Madonna's full manager in 2005, he immediately applied that forward momentum to the business model. In 2007, he negotiated her $120 million 360-deal with Live Nation - one of the first of its kind for a major artist, and a blueprint that reshaped how the industry thought about artist value beyond record sales. It wasn't just a contract. It was an argument about what music management could look like in the streaming era, before streaming was the era.

In October 2021, Guy Oseary signed Yuga Labs - the creators of Bored Ape Yacht Club - for representation. It was a first: a traditional Hollywood manager bringing Web3 IP into the mainstream entertainment machine. The move raised eyebrows in both directions. The NFT community wondered what a music manager could do. Hollywood wondered why he was wasting time on JPEGs.

Within a year, Bored Apes were on the wrists of celebrities, in music videos, and at the center of a metaverse product called Otherside. ApeFest drew thousands. The franchise expanded into merchandise, gaming, and live events. Yuga Labs was valued at $4 billion by July 2022. Oseary had done for NFTs what he'd previously done for Alanis Morissette - recognized cultural value before it was legible to the establishment, then used institutional access to accelerate it.

He also represented digital artist Beeple, whose piece "Everydays: The First 5000 Days" sold for $69 million at Christie's in March 2021 - the third most expensive artwork sold by a living artist at the time. Beeple's success wasn't just an art world story. It was a proof-of-concept for digital ownership, and Oseary was in the room when it happened.

There is also an ongoing, gently amusing subplot: Madonna has apparently not forgiven him for the specific Bored Ape she did not receive when he signed Yuga Labs. The details remain unresolved. She's still mad. This is its own form of tribute.

Every year, usually the Sunday of Oscars weekend, Guy Oseary opens his Los Angeles home for what Hollywood knows simply as "The Party." Now in its 18th year, it's a Gucci co-presentation that is considered the most exclusive after-party in the entertainment industry. Phones are banned. Gucci provides branded party favors - items stamped with "Stolen From GuyO's House." Past attendees have included Demi Moore, Adrien Brody, Nicole Kidman, Kate Hudson, and Emma Stone.

The party is a reasonable metaphor for Oseary himself. He operates with enormous access and enormous discretion simultaneously. He is, in his own words, "a people person, very approachable" who "goes out every night, tons of functions." He collects art. He has been collecting photographs, he says, since he first started making money. He married Brazilian model Michelle Alves on October 24, 2017 at Christ the Redeemer in Rio de Janeiro - a venue that presaged, if only slightly, the 1.6 million fans on the beach below it seven years later. They have four children.

He has a cameo history: Charlie's Angels, Charlie's Angels: Full Throttle, You Don't Mess with the Zohan, and Madonna's "Deeper and Deeper" music video, back in 1992. He was 20. He's been in the room where it happens, in multiple forms, for over three decades.

When asked in April 2026 whether Madonna would tour again, he said "I'm not sure yet." Then he posted on Instagram an hour later: "Of course she will tour again." The correction was faster than most people's second thoughts. That's the nature of the partnership. These days, there are no second thoughts - only forward motion.