Guy Oseary has proven himself in every field he’s taken on: as a music manager, as an early digital investor and most recently as an entrepreneur in the emerging world of NFTs and Web3 entertainment.
But for all that, he had privately catered to one bit of insecurity that he finally let go during the downtime imposed by COVID shutdowns.
“A silver lining of the pandemic is that Guy Oseary became a silver fox,” says Anthony Kiedis of the Red Hot Chili Peppers, a longtime friend and now client of Oseary. The two hadn’t seen each other for a year when “I went to an island he was hanging out on, and he was 100% radiant,” the singer continues. “He looked like a friggin’ movie star from the 1930s. Not everybody can pull that off.”
Of Oseary’s confidants, Kiedis is not alone. Says Amy Schumer: “It’s annoying that men can, like, rock the salt-and-pepper and it makes them look sophisticated and gorgeous.”
That Oseary let his hair go gray is not insignificant, as the 49-year-old had been dyeing it for the better part of two decades. The decision to see what was underneath, driven mainly by the pandemic (during which Oseary, his wife, Michelle, and their four children relocated from Los Angeles to Hawaii), was revealing in its own way.
“I didn’t know I had this much gray because I would never know,” says Oseary. “When I was 30 I got, like, a gray hair or two, and I didn’t wait to find out how many more there were.”
It’s understandable that Oseary would want to maintain the appearance of youth. The industry veteran who is Variety’s 2022 Music Mogul of the Year made his reputation as a savvy wunderkind with a magic touch and a relentless drive.
Today, Oseary’s management roster still includes the megastar who put him on the map, Madonna, as well as U2 and the Red Hot Chili Peppers. His digital investments with longtime partner Ashton Kutcher include early bets on Spotify, Airbnb and Nest, among others. Of late, Oseary has been at the center of the action on the Web3 venture Bored Ape Yacht Club, signing BAYC creator Yuga Labs as a management client and, in short order, becoming a partner — and corralling celebrity pals to bring their star power to the marketplace for acquiring Ape characters (Madonna is still mad she didn’t get the one she wanted).
In typical Oseary fashion, as cryptocurrencies and Web3 entertainment possibilities began to swirl around his rarefied circles of friends and business partners, he put his mind to learning all about it. He spent several months of his Hawaii lockdown engrossed in all things NFT — with guidance from pal Nick Adler, Snoop Dogg’s Web3 advisor. At the end of the exercise, Oseary recalls, “I stood back and thought, ‘OK, I now understand.’ But I didn’t understand. So I said, ‘I’m going to learn on the job and focus on the talent.’”
Oseary’s work to connect the dots for talent in the latest emerging market is in keeping with his roots as an ambitious teenager who hustled his way into the business — first, by wowing legendary manager Bernie Brillstein, and then by latching on to Ice-T’s DJ Evil-E as his first major signing. Oseary recalls using the rapper’s credentials to sneak into industry confabs like the New Music Seminar. Kiedis remembers Oseary borrowing his pass to take in New York’s CMJ: “I saw the love in his eyes for the life of music; that is the world he wanted to live in.”
Oseary was barely out of his teens in 1992 when he started as an A&R executive at Maverick, Madonna’s Warner Bros. Records-based label. He got the gig by offering to work for no pay, “just an office and a phone,” for Madonna’s then-manager Freddy DeMann — whom he had met through schoolmates at Beverly Hills High, enrolling in the district by using a family friend’s address. Maverick would soon become home to hitmakers Alanis Morissette, Candlebox and Prodigy.
Madonna vividly recalls first meeting a barely legal Oseary. “I thought, ‘Who the hell is this young punk with all the opinions and stuff?’ He was super naive, but I also thought he had a lot of chutzpah,” she tells Variety.
For his part, Oseary credits Madonna with pretty much everything. “She mentored me and, by working so hard, pushed me to work so hard,” he says. “I didn’t know shit until she grabbed me by the hand and said, ‘Let me show it to you.’ We had a really good brother-sister relationship, then as the years went on, I became the dad you want to rebel against, and now I’m like grandpa. She’s like, ‘You are so fucking boring. I don’t even know why I have you around.’”
In his three decades at the top of the music business, during which his acts broke touring records and ushered in the first-ever 360 deals with Live Nation, Oseary has traipsed with wide eyes through a world of stadiums, movie sets, red carpets, museums and, yes, yachts. He has hobnobbed with presidents (Clinton, Obama), movie stars (Matthew McConaughey, Woody Harrelson, Chris Rock, Adam Sandler, Ben Stiller), business titans (Salesforce’s Marc Benioff, Sean “P. Diddy” Combs) and moguls turned philanthropists (David Geffen). He’s become a matchmaker of minds and talent with a very deep Rolodex.
Oseary’s next act as mogul, however, places him firmly in a playground of adults — specifically high-net-worth ones. Thanks to his prescient and profitable investment strategy, he’s steered Sound Ventures, his eight-year-old tech fund with Kutcher, to invest approximately $600 million in platforms across a wide spectrum of sectors, including social networks, fintech, alternative energy, health care, mobile gaming, sustainability, virtual fashion and SaaS (Software as a Service).
More recently, Oseary has gone all in on NFTs through Yuga Labs’ Bored Ape Yacht Club, one of the most successful and well-known original NFT brand launches to date. Last spring, BAYC and its offshoot Mutant Apes helped Yuga Labs raise $450 million in a seed-funding round that put its valuation north of $4 billion. Oseary’s investments in the space also include the World of Women collection and the artist Beeple, whose project “Everydays,” a collage of 5,000 art pieces created daily over 13 years, made history, fetching $69 million at auction, Christie’s highest-ever bid for a digital art piece.
Oseary’s hot hand in the volatile digital area doesn’t surprise his friends and colleagues.
“I’ve always said to Guy, ‘You’re much more than a music manager,’” says Michael Rapino, the CEO of Live Nation and a longtime business partner of Oseary, as well as a friend. “‘Your real strength is investing and building businesses, being early on them and connecting the dots.’ I was very supportive of him getting into new verticals.”
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Age is on Oseary’s mind these days as he counts down to his 50th birthday in October. With all that he has on his plate, he makes frequent trips to Israel to visit his mother as often as his globe-trotting schedule allows. In fact, it was in Tel Aviv in May that Oseary first sat for a series of interviews with Variety, fresh off a plane from L.A. and just before heading to New York for ApeFest (more on that later), then London and Paris for the Red Hot Chili Peppers June stadium gigs. In July, he’ll spend much of the month sailing the Adriatic Sea before moving on to the south of France.
“Eize yoffi,” says Oseary in Hebrew — translation: “how nice” — as he gazes out from the penthouse suite of Tel Aviv’s Dan Hotel to the beach below on a cloudless May morning. “It’s one of the most beautiful places people don’t know about in the world,” he says with a sigh. “So much good to give, and yet so complicated.”
It was about a year prior when a controversial ground-to-air war in the Gaza strip divided the music industry. As tension escalated and Israeli military action pummeled the tiny area of land — including cratering a building housing the Al-Jazeera news network — label executives, artists and influencers sympathizing with the Palestinian cause got louder, and those who identify as Jewish supporters of the state of Israel were forced underground, especially on social media.
Oseary did not subscribe to the duck, cover and wait it out approach, and on May 11, 2021, wrote to his more than 200,000 Instagram followers: “PEACE!!!! PLEASE!!!! Can someone rise up and help stop all the suffering of our Arab brothers and sisters and our Jewish brothers and sisters. I’m watching with a broken heart. We are one!”
Oseary has a distinct vantage point on Israel and the many issues that have roiled the region for centuries. He was born to parents of Moroccan and Yemenite descent and spent his childhood in Jerusalem raised with what he calls “Jewish Arabic culture.” He has wittingly inserted, and asserted, himself as an unofficial ambassador of Israel to the entertainment world at large.
His efforts include not only bringing Madonna to perform there — twice on tour, in 2009 and 2012, and in 2019 for “Eurovision”— but meeting politicians (the late Shimon Peres “was a beautiful man,” says Oseary); talking with business leaders (like Bashar Masri, the Palestinian entrepreneur behind Rawabi, the first Palestinian planned high-tech city); and encouraging musical collaborations.
While not observantly religious, his Jewish identity has also put him at the center of verbal volleys related to antisemitism. In 2017, Oseary defended Jay-Z publicly when the rapper’s track, “The Rise of O.J.,” was criticized for the lyric, “You wanna know what’s more important than throwin’ away money at a strip club? Credit / You ever wonder why Jewish people own all the property in America? This how they did it.”
“If you listen … in its entirety you will hear that the song is based on exaggerated stereotypes to make a point,” Oseary wrote at the time. “I’m not offended by these lyrics. I hear them the way he intended them to be heard. … Giving ‘credit’ to a community that supposedly understands what it means to have ‘credit.’ I’m good with that.”
(The Anti-Defamation League agreed, publicly stating, “We do not believe it was Jay-Z’s intent to promote anti-Semitism. On the contrary, we know that Jay-Z is someone who has used his celebrity in the past to speak out responsibly and forcefully against the evils of racism and anti-Semitism.”)
Three years later, Oseary found himself counseling Nick Cannon on the heels of antisemitic rhetoric the “Masked Singer” host voiced on his podcast. Again, the offending stereotype involved Jews and money.
“I saw Puffy, who is one of my best friends, say something supporting Nick,” recounts Oseary, who’d never met Cannon before. “Puffy was, like, ‘He’s a brother and a good guy.’ So he put us together and I’ve never seen anyone so genuine about wanting to learn. There are some landmines that Nick didn’t understand — words that were hurtful, easy-target stuff. And he really put the time in. He could stay on the phone all night and just talk about it. I thought, ‘Wow, this guy’s getting killed out there, and yet he’s calm.’ I was really impressed by how much he cared. He was coming from the right place.”
Oseary grew up in a home where Arabic and Hebrew were spoken, unaware of the dividing lines between religion, politics and class. Not that he was sheltered in his youth. To the contrary, “in Jerusalem we were all just together,” he says. “We listened to the same music, ate the same food. We all hung out at the shuk [flea market]. I didn’t really understand until later of the inherent problems.”
He vowed to be part of the solution. “You always hear, ‘Nothing will change; it’s always going to be like this,’ and I refuse to believe that,” he says. “To figure out how to solve these issues just takes communication. How do you work together if you can’t even meet to talk? There’s got to be a start somewhere.”
Described by friends endearingly as “socially awkward,” Oseary is a natural conversationalist once you get him going. (Want to grab his attention? Fawn over Depeche Mode.) But make mention of his “Arab brothers and sisters” and there’s a pronounced difference in his tone as frustration meets conviction.
“You don’t hear the stories about when people do get along,” he says. “There are two million Arab citizens of Israel. There are Arabs and Jews working side by side. There’s a whole lot of goodness to go along with the insanity. And there are people in the middle trying to solve it that are just not the loudest. … I see people come at me because I’m Israeli, saying, ‘you support this’ or ‘you support that.’ It’s like, you don’t know me. I don’t want to have where I was born be a deciding factor on whether you like the people I work with or want to support them. But talk to me. We don’t have to agree. I am happy to learn. And happy to help.”
Oseary put some of these thoughts to words in June, 2011 on the heels of the Arab Spring when he authored an op-ed for Al Jazeera, the rare Israeli to do so. It didn’t prove to be a home run as Oseary was taunted for being a hopeless optimist. “There are so many other people at play who gain from the negativity and from making sure things don’t work out,” he says. “The ‘don’t work’ contingent is way more well-financed than the ‘make it work.’”
But criticism hasn’t deterred Oseary, who has sprung to action more than once in the wake of tragedies that have taken the lives of the innocent. In 2018, he helped raise money for Pittsburgh’s Tree of Life synagogue following the mass shooting that killed 11 congregants — to drive the point home, he accompanied his public plea with a photo of his himself visiting Auschwitz tearfully holding an Israeli flag outside a former prisoner housing unit. A year later, Oseary launched a GoFundMe for victims of the 2019 terror attack on a ChristChurch New Zealand mosque, where 51 died. Between Chris Rock, Ben Stiller, Madonna and others, $150,000 was donated.
“I believe some young kid out there who sees the bigger picture will figure out how to solve some of these problems, which are solvable — they’ve been solved in many places and can be solved here,” he adds. “And it’s not just on Israel, on all sides: where are the leaders we can all look up to? It’s been the same leadership for 30 years. … I’m turning 50 and I’m building a lot of my work off of new ideas, not 30-year-old ones. In order to move it forward, you’ve got to search out innovative minds.”
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Oseary has always been drawn to innovators, entrepreneurs and the cutting edge — that mix of chutzpah, good taste and savvy that first impressed artists like Madonna and Kutcher. “We’ve been working together for 15 years now and I know very little about his music business,” offers Kutcher. “But speaking on Guy as an investor, he is able to synthesize a lot of information and determine what it is that people want. He’s kind of like a heat-seeking missile in that perspective. He doesn’t always get into the weeds of the economics of a deal so much as understanding the extent that people are going to want that service.”
Kutcher’s motto: “founders first,” Oseary explains of their approach to potential investments. “He thinks: ‘Do I want to work with this person? Would I want to leave my job and work for this guy?’ I’m more on the ideas side. Like, do I love this idea enough to want to do it myself? That’s how much I love it. The other thing we look at is: can we help it? Can we really do something here? That’s the foundation. To me, it’s very similar to walking in a room and recognizing an amazing artist.”
Sound Ventures continues to identify platforms poised to break. But Kutcher and Oseary were initially greeted with skepticism by Silicon Valley.
“When we first started, it would be absolutely understandable for anyone to underestimate both of us,” Oseary says. “You know, music guy, actor guy — these guys are going to be tech investors? But he has an engineering background and I have an identify-talent background, so watch out.”
Today, one fellow music industry player describes Oseary’s investment prowess as “second to none — I’m in awe, and a little jealous.”
When it came to NFTs — non-fungible tokens, which were all the rage during the pandemic — wrapping his head around the tech was in itself a dizzying exercise. Still, Oseary was determined to understand how it all works: specifically the crypto-supported market for collective digital art, the blockchain technology that powers transactions and ownership and the smart contract that allows any artist, when they resell their work, to earn forever. “Every time it trades hands, you still get paid,” says Oseary. “And it doesn’t matter if you’re Madonna or Shmadonna — you’re probably getting paid the same deal.”
Indeed, Madonna is still fuming over getting beat out for Bored Ape No. 3756. “I was hellbent on getting an Ape and really specific about what I wanted: the Ape with a leather motorcycle cap on and multicolored teeth,” she says. “I was told that it was inspired by me, and modeled after me, and it was bought by a woman who’s a fan of mine. She was gonna sell it to me, but it was way too expensive.” (That Ape is currently priced at 800 ETH, around $1.2 million; instead, Madonna eventually purchased Ape No. 4988, for which she paid the equivalent of $466,000.)
Such is the nature of NFT marketplaces like OpenSea, and it was there that Oseary first looked at planting a financial stake. That is, until he refocused on what he knows best, namely talent.
Talent, in the NFT ecosystem, are artists like Beeple (real name: Mike Winkelmann), with whom Oseary very quickly linked, connecting the dots to his client world (a Madonna-Beeple collaboration called “Mother of Creation” came to fruition in May as a work of digital surrealism depicting “Mother of Nature,” “Mother of Evolution” and “Mother of Technology”) and industry peers. The two are currently partnered in WENEW, parent company to 10KTF (for “10,000 True Fans”), a beloved weekly serial disguised as an NFT wearables project.
Oseary gravitated toward Bored Ape Yacht Club, a digital series that started with 10,000 unique Apes available for purchase and trading, which drew a frenzied response out the virtual gate on its way to racking up $2.3 billion in sales to date, according to CryptoSlam.io.
The series serves as a kind of fan club on steroids that encourages owners of the NFTs to move through an ever-growing and exclusive list of events and opportunities. The BAYC and its offshoots have drawn the attention of celebrities (Tom Brady, Justin Bieber, Kevin Hart, Jimmy Fallon, Post Malone) whose involvement has added momentum to the community-building effort. To date, BAYC is the highest-profile tangible example of what NFTs and Web3 platforms might mean for traditional Hollywood players.
“In this space, there’s a lot of people who are full of shit, or if they’re not full of shit, they’re trying to sell you a bunch of bullshit,” says Beeple, who first facilitated an introduction between Oseary and Yuga Labs. “I think Guy is trying to build something that’s real.”
Considering the volume at which the Apes have been trading (the 10,000 minted NFTs, held by some 6,458 unique owners, had a total market cap of $1.4 billion, per CoinGecko, as of July 24), even the Yuga Labs founders — Zeshan (aka No Sass), Greg Solano (Gargamel), Kerem (Emperor Tomato Ketchup) and Wylie Aronow (Gordon Goner) — are astounded at its success.
“We didn’t really know why he was so interested in us — it was a little perplexing,” remembers Goner of Oseary. “But he’s become integral to the process of basically everything that we do. Guy is wired for this like no one I’ve ever met.”
“They reminded me of a band,” says Oseary of Yuga. “You had the singer, the guitar player, the drummer, the bass player… and I have some experiences working with bands. Gordon and I connected a lot. Music is in his in his blood and his favorite band in the world is the Bad Brains, who I signed and reunited, so we had a nice rapport.”
Goner’s reaction to that factoid was of demonstrably greater astonishment. “He asked me who my favorite bands were, and I said Bad Brains and KRS-One. He gets out his phone and shows me a photo after, like, two minutes of scrolling, of him at 16 years old with KRS-One in Brooklyn, and I’m, like, ‘What the fuck is going on?’ Then he shows me a picture of him and H.R. from Bad Brains. These are two very different bands — one is old school hip-hop and the other DC hardcore. I was, like, this is incredible. And I quickly kind of fell in love with the guy, pun intended.”
Since Oseary came aboard Yuga, which also owns the popular series Cryptopunks, the Ape universe has grown at breakneck speed, rolling out multiple drops of limited-edition digital avatars along with NFT wearables, its own metaverse (the Otherside) and a four-night event in New York City called ApeFest that coincided with June’s NFT.NYC conference and featured appearances by Eminem and Snoop Dogg (the two debuted their “The D 2 The LBC” collaboration) and performances by Haim, Lil Baby, LCD Soundsystem, Lil Wayne and Future.
The festival, which was accessible only to Ape owners, arrived with a starry party at the South Street Seaport blocks from Wall Street, just as the digital currency began its free-fall that has seen the crypto market lose more than half its value since the start of 2022.
Oseary says he is completely unfazed. “Welcome to crypto,” he deadpans. “It’s volatile. It has its bumps and it will have its run. But I believe in it.”
Snoop, whom Oseary contends is the only artist who really understands the NFT world, agrees. “We’re weeding out the true players from the crowd,” says the multi-hyphenate of the so-called Crypto Winter. “This market is down, but the real ones are staying up. We don’t do this to get in and out; we do this to stay for the long run. You just have to let it run its course and make things happen in the meantime.”
”You can’t step into this world and expect the community to hand you the keys. You got to be in the streets before you step into the suites. It’s just like the real world. Hustle first then play.” — Snoop Dogg
Oseary’s portfolio also includes a partnership with World of Women, a series of NFT collectibles founded by Yam Karkai. The art industry, Oseary challenges, has not historically been inclusive of women. “Rattle off your top 20 artists, let me know when you get to a woman,” Oseary snaps. “All of this [NFT] money that’s coming in, less than 2% goes to women.”
To that end, WoW has partnered with Reese Witherspoon, who serves as partner on TV and film projects. “All of this is early days,” he says of the project in development. “Where, in the music world, artists are given a few years to put together the next album or tour, in the crypto world, things move so fast. Everyone expects you figure it all out in three months.”
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Oseary was never one to play the stock market. He winces remembering the recent nosedive his Peloton shares took, and that he cashed out his Bitcoin at $250. He’s learned through experience that overextending can flatten you in an instant. When he was 27 and just starting to put away some money, he lost his entire savings to the dot-com crash.
The venture that sunk Oseary was, ironically enough, brightly titled Idealab, an early digital business incubator run by famed investor Bill Gross. Oseary spent a year with the founder, who’d proven his Silicon Valley savvy by launching three billion-dollar companies in quick succession. Oseary would forgo stakes in Vitaminwater and Research in Motion, the maker of BlackBerry, to go all in.
“I lost everything on that one deal — all the money I ever made and saved,” he says. “It also stopped me from being entrepreneurial and innovative and taking risks. I had to, like, survive for a while. It happened so quick, like I’d just been punched in the gut. I was a walking zombie. I only thought about it, like, 100 times a day.”
The result: “A little humility,” says Oseary. “It’s not all there. You’re not all that. You’ve got to feel a little pain to start. You’re going to make some mistakes. And that was a painful mistake. They say that 27 is the year … you don’t make it out of it. And a death of sorts definitely happened.”
A little more than a decade later would come another fumble, albeit without the hit on his wallet: The 2014 rollout plan for U2’s “Songs of Innocence” included the unprecedented step of a partnership with Apple to drop the album simultaneously on every iPhone in the world. Oseary still insists it was a good concept — the band had tasked him with getting the music to as many people as possible. The problem was the tech.
“Sorry to anyone who will be disappointed by what I’m about to say, but I look at it as, it was awesome that their music went to everybody. But maybe not so awesome that a small group of people were upset for receiving a gift that they didn’t ask for. But I don’t regret it,” he says. “And I’m not representing the band when I say that. … The technical side of things, I didn’t foresee that part. We probably should have explained more or had an ‘opt-in.’ But I’m a student of trying new things. Think about Prince or Radiohead — people thought they were crazy. Taking chances doesn’t come without risk, and I don’t want to be fearful. If given the opportunity, I would do something like it again.”
“Think about Prince or Radiohead — people thought they were crazy. Taking chances doesn’t come without risk, and I don’t want to be fearful.” — Guy Oseary
Ultimately, the stunt did have the desired effect. “I saw firsthand that, when we did the ‘Innocence + Experience’ tour, a majority of the audience knew all the new songs,” says Oseary. “And we did indeed share the music with as many people as possible — a half billion Apple consumers. Goal accomplished.” Nonetheless, the incident certainly was a test of the band’s relationship with its new manager. Oseary says he was handed a “great responsibility” in 2013 when U2’s longtime manager Paul McGuinness retired and encouraged the band to go with Oseary.
“Trustworthiness is an old-school term, and whilst the manager-client relationship does not require a Hippocratic oath, Guy O. takes this very seriously,” U2’s Bono tells Variety. “That’s one of the reasons we work so well together. He is a most trustworthy person. In the early days, the temperature could get raised as we would debate different aspects of how we go about our business. But in recent times, not so much. He feels like family.”
The family construct comes up a lot in conversation with Oseary. “He’s like my brother” is a refrain one hears attributed to the likes of Kiedis, Kutcher, Rock, McConaughey and Owen Wilson. Sister is used to describe Madonna and Penelope Cruz. And when, in 2015, Oseary re-launched Maverick as a collective of managers — including Sal Slaiby (The Weeknd), Scott Rodger (Paul McCartney), Clarence Spalding (Jason Aldean), Cortez Bryant (Lil Wayne) and Gee Roberson and Adam Leber (Lil Nas X), among others — the concept centered around an extended family of artist representatives with shared goals.
The new entity, brought together under Live Nation, Oseary asserted at the time, “is not a rollup.” Explaining the concept in a 2015 Billboard cover story, he said: “I consider it a collective under one brand, with the goal of helping clients reach their potential.” The Maverick 2.0 experiment lasted five years, after which Oseary “stepped down” from his role at its helm and partner managers unbuckled.
Did it fail? That’s hard to say considering all remain under the Artist Nation umbrella and continue to bring in profit to the parent company, Live Nation. In fact, some of those managers — like Ron Lafitte, whose Patriot Management represents Ryan Tedder, Maneskin, Pharrell Williams — are having a tremendous few years. That the 17 managers never fully integrated the economics of their businesses might speak more to competing egos than financial sense, according to key players, whom of whom saw it as a branding exercise than a scalable business.
The way Rapino views it, “I think ultimately Guy’s entrepreneurship was more important and a bigger opportunity for him than trying to manage managers. I would remind him, ‘You manage U2 and Madonna — you don’t need more horsepower than that.”
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Clout-chasing is not an uncommon practice in music, but nowadays, the stars come to Oseary. For proof, look no further than his annual Oscar afterparty. The ultra-exclusive soiree has been held at Oseary’s home since 2008 with a strict no-pictures-allowed policy. The guest list has included not just top actors but the likes of Jeff Bezos, Elon Musk and Benioff.
In his answer to the Vanity Fair Oscar party, Oseary saw the need for a celebration that is “designed for talent to feel free” — from media of all kinds. “This is their last party before they go home and fly off to their next movie, and the only chance to take off their shoes and dance or just sit and have a dinner and not have a camera in their face,” he says.
“I have been a couple of times, and invited many more,” says Kiedis, describing the room as “friggin’ overwhelming.”
Schumer, a former client who took on Oseary as a manager shortly after she opened for Madonna on her 2015 “Rebel Heart” tour, attended for the first time this year, a few hours after she co-hosted the Academy Awards ceremony where Will Smith shocked millions of people around the world by slapping Chris Rock onstage. Rock also wound up at Oseary’s, not surprisingly given their close relationship. Schumer says the intimacy of Oseary’s home after the jolt from the slap lent the gathering an air of “incredible generosity.”
“I don’t want to get too into it because it’s so fucking volatile and so heavy,” says Oseary when asked to reflect on that night. “I’m just happy that I saw [Rock] as close to that happening as possible because that’s my brother and the godfather to my daughter. He was a class act. I never would have reacted the way he did. I couldn’t have. So I’m glad that we were all there to greet him with the love he deserves.”
Oseary is known for his grand expressions of love. He and Brazilian model Michelle Alves married in 2017 with a ceremony in Rio de Janeiro at the site of the Christ the Redeemer statue. At 2,300 feet, the pair stood under a chuppah, a ceremonial canopy used in Jewish weddings, that was carried by Rock, Kutcher, Kiedis and actor Owen Wilson.
“I thought that was pretty ballsy for a Jewish dude!” cracks Bono of the chosen location, which saw dozens of A-list friends make the trip to Brazil. “It was a very Guy O. situation: spectacular — on an emotional level too. Even the clouds conspired to keep the paparazzo away.”
Madonna delivered remarks at the reception that were so sassy one fellow guest remarked, “You wondered, ‘Does she actually like this guy?’” (For the record, says Oseary: “If anyone has the absolute right to poke fun at me, it’s her!”)
“For a long time, “I had him all to myself,” Madonna says. “And then he got married and I had to share him with his wife, which really pissed me off. Because before, it was a lot of pretty girls that just came in and out, but then he settled down with a really nice girl. And I was like, ‘Goddamnit, now I got competition.’”