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Leonardo DiCaprio has been nominated for an Oscar several times throughout his career. At one point, Jamie Foxx managed to claim an Oscar win over DiCaprio when they were both nominated the same year.

But it was an outcome that DiCaprio’s ex-girlfriend at the time thought might have been a mistake.

Gisele Bündchen went to the Oscars to support her then-boyfriend Leonardo DiCaprio

Leonardo DiCaprio and Jamie Foxx posing at the the "Django Unchained" photo call.
Jamie Foxx and Leonardo DiCaprio | Matt Dames/Sony via Getty Images

Bündchen formed a relationship with DiCaprio in the year 2000. The pair dated for five years before deciding to part ways in 2005. Throughout their relationship, the super-model was introduced to the lifestyle of a celebrity actor, which included a night out at the Oscars. Years later, Bündchen would reflect on what it was like attending the ceremony for the first time with DiCaprio.

“When you go to a place like the Oscars, there’s, like, a lot of people and everyone is screaming,” she described. “I remember just feeling a bit, like, squeezing his hand and being, like, ‘OK, I’m here,’” she once told British Vogue.

Bündchen went on to confide that she had particularly fond memories of, not only her time there, but her wardrobe.

“It was nice to experience that once in a lifetime,” she recalled. “And I love that dress.”

Bündchen attended the Oscars when DiCaprio was up for a nomination for the feature The Aviator. But that year, he lost to Jamie Foxx for his performance in Ray. Bündchen believed she may have been much more disappointed than DiCaprio was with the results.

“He’s not just my boyfriend but he’s an amazing actor. He’s really talented and I was so proud of him. I figured I should go and support my man so I went there just for that reason,” she once said according to Contact Music. “I don’t think he was expecting to win. I think I was more upset because I thought he deserved it more than [Foxx]. I was like, ‘He did a better job than [Foxx]!'”

How Jamie Foxx felt about winning the Oscars

Like DiCaprio, Foxx also didn’t expect to win the award. So much so that during the Oscar campaign, Foxx admitted that he wasn’t acting professionally.

“When I was up for the Oscar I didn’t take it seriously at all,” Foxx once said according to IndieWire. “I thought there was no way to win that. I took [Oscar season] as an excuse to party. I was like, ‘Oh, I’m nominated? Break out the champagne and let’s party.’ I remember having paparazzi on me for the first time. I remember going absolutely nuts. I went to the Golden Globes and there was champagne involved and I was just wrong on the red carpet. I was disrespectful to the process.”

But Foxx would actually pick up the award that year, which led to an emotional moment between him and his childhood friends.

“Everybody was crying. Speedy, a friend I’ve known since I was Eric Bishop, and all the other guys couldn’t hold back. Because it’s like this: Halle and Denzel are supposed to win the Oscars. Speedy and I were always just a couple of Wet Willies [pranksters] with cops harassing us. You know how our folks are: When one of us wins, we all just want to celebrate,” he once told Oprah.

Leonardo DiCaprio felt it would’ve been a ‘catastrophe’ if he won an Oscar for his earlier film


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Speaking to Time Out, DiCaprio revealed that he rarely thought about Oscars when performing in movies.

“Honestly? It’s never ever what I’m thinking about when I’m making movies. There’s nothing I’ve done for the specific reason of getting an award. Every single time you just go in there trying to bat a thousand, trying to give it your all,” he said.

But there was one film DiCaprio might have been thankful that he didn’t win the Oscar for. He was 19-years-old when he was nominated for What’s Eating Gilbert Grape. He felt there was a good chance he would’ve embarrassed himself if he won that night.

“I had absolutely nothing prepared. I didn’t think there was a shot in hell I’d get it. It would have been an absolute catastrophe if I had,” he said.