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The Wildest Stories From Madonna’s Legendary Oscar Parties

What better way to get “into the groove” than with the Material Girl herself?

When Vanity Fair canceled its annual Academy Awards party due to the Writer’s Strike in 2008, it created a void—one Madonna, Demi Moore and Guy Oseary were happy to fill. It was that year that the trio hosted their inaugural after-party, the most exclusive event of award season. “Just wearing a fantastic dress and having lots of great jewelry—that’s my part of the planning,” the pop singer told Q magazine later that year. “And making sure there are no photographers.”

After a night of being camera-ready, stars look forward to kicking off their heels, loosening their bowties and letting their hair down. As a guest once told The New York Post’s Page Six, “People go to the Vanity Fair party to be photographed, then they go to Madonna’s to party in private.”

Madonna Oscar Party

Madonna has hosted the event at her manager’s home every year since, even in absentia. Moore, meanwhile, has not co-hosted the bash since her divorce from Ashton Kutcher; Oseary is the Kutcher’s investment partner.
The first party drew a large crowd that included a then-married Tom Cruise and Katie Holmes, as well as Ellen DeGeneres, Portia De Rossi, Cameron Diaz, Eva Mendes, Christian Slater and Owen Wilson. “There were Le Tourment Vert absinthe fountains flowing all night—it was insane,” Page Six reported. “Diddy grabbed the mic rallying everyone to dance.” As party planner Jeffrey Best once told Robb Report, the hip-hop mogul “moved that party to a height I’ve never seen before. There wasn’t a single person who wasn’t dancing.” And, despite Madonna’s long-time feud with Elton John, he was spotted “getting down” with David Furnish.

In its second year, Madonna was spotted dirty dancing with notorious party girl Lindsay Lohan. As E! News exclusively reported at the time, the Best Events-produced event was set up under a temporary atrium adjacent to the house, lit by chandeliers. Ashton Kutcher shared some of the “coolest moments of the night” via Twitter, like meeting Jack Nicholson, holding Penélope Cruz’s Oscar statue and seeing Joe Pesci send back three martinis “because they were sub par.”

Cut to 2010, when Diddy commandeered the microphone. At one point, he stopped the music and said that unless Anderson Cooper began dancing, he wouldn’t play any more music. The CNN anchor obliged and the party raged on. Guests were served Indian food, and there was also a special drink: the Vita Coco Caipirinha. (Madonna and Moore are investors in the brand.)

By 2011, the party was already becoming the stuff of Hollywood legend.

So, Jenny McCarthy did what anyone in her position would do: she crashed it.

“Me, my girlfriends and my sister were hanging at my house in the Valley, watching the show. I don’t usually watch the Academy Awards because it’s a reminder of everything you failed at, especially if you’re in this business,” she later told Entertainment Weekly. “But my friends thought it would be a good idea to watch the Academy Awards whilst getting completely lit.”
“We sat around, and between five of us, I think it was, we went through about six bottles of champagne. It was the best Academy Awards show to date,” she said. “And one of my friends said, ‘Hey, Madonna has an after-party every year at Guy Ritchie’s house. We’re in the Valley—it’s in the Valley—Why don’t we crash it?’ I had one too many and I had confidence like I’ve never had before. And I looked at my girlfriends and my sister and we were in our pajamas. We were hot messes—just gross. And it was midnight at this point, and I said, ‘Screw it. Let’s do it!'”

[Editor’s note: McCarthy confused Ritchie, Madonna’s ex-husband, for Oseary, Madonna’s manager.]
“We got in the car and drove to Guy Ritchie’s house—because everybody knows where everybody lives in L.A.—and we get line the line. It was a huge line! We pull up to the guy and guys surrounding him with clipboards, and I rolled down the window and I go, ‘Jenny McCarthy.’ And he goes, ‘I don’t see your name.’ I [firmly repeated], ‘It’s Jenny McCarthy.’ He looks back and he goes, ‘I know. I don’t see your name.’ I go, ‘Well, it’s there! I know it’s there. I’m on the list!'” she said. “He goes, ‘How many people do you have with you?’ I say, ‘Just six.'”

“Now, most people can only bring one person, and this party isn’t like a party where celebrities get to bring their friends. Not even B-celebrities can get in there. This is only A+++ celebrities—not even directors, not even producers, just big time. So, here I am asking for six people to get in,” McCarthy said. “And the guy goes, ‘Just go.’ So my friend hit the gas pedal and we were like, ‘F–k yes!’ We pull up and we go inside the house and every single person is a huge celebrity: Bradley Cooper, Renée Zellweger, Gwyneth Paltrow, Tom Hanks, Meryl Streep—you name it!”
McCarthy wound up “losing everybody” in her group, as they were all busy stalking their favorite stars. “I’m outside and I look through the big glass window and I see this body rolling down the stairs, a cloud of dust—and a thud!—and I realize my sister just fell down a flight of Guy Ritchie’s stairs,” the radio host continued. “I scraped my sister off the ground, grabbed my other friends who were trying to get down on Bradley Cooper, and we hopped back in the car and drove home and laughed and said, ‘Oh, my God! This was one of the greatest nights ever.'”

Ed Sheeran pulled a similar stunt in 2014. “I went to an Oscars party at Madonna’s manager’s house by saying I was Calvin Harris. It was at a time when no one knew what he looked like, just the DJ name, and I was with my cousin and Rita Ora,” he told New York City’s 92.3 AMP Radio three years later. “Rita Ora was with Calvin Harris at this point. She said, ‘Calvin’s on the list and I know he’s not coming, so just say you’re him.’ I walked up to the door and said, ‘Hi, I’m Calvin Harris,’ and they were like, ‘In you go, sir.’ It was a really amazing party—Prince was there, actually. The first person I saw when I walked in was Prince. Apparently Calvin Harris was there, a bit shorter and a bit less Scottish, a bit less abs…That was quite a funny thing.”
But it’s not just about the guests—it’s also about the swag. Per The Hollywood Reporter, in 2012, David Beckham, Victoria Beckham, Sandra Bullock, Leonardo DiCaprio, Colin Firth, Jodie Foster, Salma Hayek, Mila Kunis, Katy Perry, Gwen Stefani, Emma Stone and Kristen Wiig walked away with Gucci gifts. The fashion label hired a special Florentine artisan to hand-emboss the initials of each guest on signature pieces of Gucci luggage—at no expense to the stars, of course. As if that weren’t enough, guests were also given pairs of sunglasses. Not that Hayek—whose husband, François-Henri Pinault, owns the Gucci Group—needed the freebies.

What they could’ve used, however, was less booze and more water.

Take it from Sam Claflin, who attended in 2013. As he told Elle, “I was pretty far gone by the time I got there so I don’t remember many details. I should have stolen some toilet paper. It was after a big event…Everyone’s there and everyone’s loose. I remember spilling a whole glass of red wine down somebody. There was an epic selfie of me, Lily Collins, Selena Gomez and Vanessa Hudgens at some point. I was about to work with Lily Collins, so she kind of looked after me I suppose. I was there with my agent and Jared Leto, who was hanging out with us.”

According to Claflin, “It was really bizarre…Honestly, we spent a long time together, but you just don’t know [if Leto would remember me]. I mean, everyone, especially me, was so drunk.”
When the actor appeared on Bravo’s Watch What Happens Live in 2016, he explained that Madonna was unaware of his party foul and provided a few more details from the wild soirée. “I was jamming with Selena Gomez and Vanessa Hudgens. I’ve never seen them ever again—I think, probably, because of the red wine incident,” he laughed. “Derek Hough and I…why I challenged him to a dance-off, I have no idea. I basically had a glass of wine that went all over his tux and all over the floor. It was on a dance floor—it wasn’t on a carpet. It wasn’t on a rug.”
Claflin’s Hunger Games co-star Jennifer Lawrence made a splash a year later—albeit not the kind any guest would have wanted to make. As she later recalled on NBC’s Late Night With Seth Meyers, she brought her best friend Laura Simpson as her date to Madonna’s “big fancy party.” It was the kind of party, Lawrence joked, where “if you get invited, you’re like super-important.”

But the joke was on Lawrence. “I puked on [Oseary’s] porch. I was in such bad condition,” she confessed. “I look behind me while I’m puking, and Miley Cyrus is there like, ‘Get it together.'”

After Lawrence shared the story with Seth Meyers, Cyrus tweeted, “That never happened.” Within moments, the “Adore You” singer deleted her tweet without offering any explanation. Thankfully, Lawrence was able to stave off her hangover: As E! News’ Marc Malkin reported at the time, McDonald’s supplied a late-night menu of breakfast foods, including Egg McMuffins.

Eddie Redmayne commiserated with Lawrence on The Graham Norton Show in 2015. “This is something I have never admitted to the world,” he said, “but I puked at Madonna’s party, too!”
Lawrence shouldn’t feel too bad about her embarrassing moment, considering Kelly Ripa somehow managed to make an even worse impression on Madonna that night. As she once revealed on ABC’s Jimmy Kimmel Live!, “I gave her a full hug, and then I inhaled her hair like a weirdo. She smelled like gardenias. I said, ‘Mmm, you smell so good.’ She goes, ‘OK, that’s all right.’ Maybe I won’t be invited back. [But] if you walk in like you belong, people will let you in.”
Though Madonna skipped her party in 2015 to rehearse for her performance at the BRIT Awards, it still brought out the biggest names in Hollywood. She missed the party in 2016, too, due to a previously scheduled concert in Singapore. Oseary handled hosting duties in her absence, inviting Ben Affleck, Benicio Del Toro, Sylvester Stallone and other stars to let loose. Female guests left with a velvet and crystal ring from Alessandro Michele’s first collection as the creative director of Gucci, while male guests left with a pair of Gucci feline head cufflinks.
Don’t expect to ever see any photos from this year’s bash. “There are plenty of other social settings before this party where celebs can take pictures of themselves and share it on social media,” Best explained to The Robb Report. “We want people to be free to dance and not be concerned what a photo of them would look like after spending three hours on a dance floor.”

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