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Jimmy Kimmel Jokes About Leonardo DiCaprio’s Sex Life After His Oscar Win: ‘Every Year Is His Year’

It’s funny because it’s true. After Leonardo DiCaprio finally won an Oscar for his role in The Revenant at the 88th Academy Awards on Sunday, February 28, Jimmy Kimmel couldn’t help but joke that despite that big win, DiCaprio, 41, has been getting lucky for quite some time!

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“Leonardo DiCaprio won best actor. Leo had been nominated six times, but until tonight, he never won,” Kimmel, 48, said during his opening monologue last night on his post-Oscars show. “But everyone kept saying this is his year.”

“And it was. But the man has had sex with a different Victoria’s Secret model every night of his life,” he quipped. “Every year is his year. From 1991 on has been his year.”

Jimmy Kimmel
Jimmy Kimmel

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DiCaprio is known for his penchant for dating world-famous supermodels. While several Victoria’s Secret models (current and former) including Gisele Bündchen, Erin Heatherton and Toni Garrn have made their way onto his long list of ex lovers, the Wolf of Wall Street star’s most recent relationship was with Sports Illustrated stunner Kelly Rohrbach.

Leonardo DiCaprio and Kelly Rohrbach attend the Men's Final on day 14 of the 2015 US Open at USTA Billie Jean King National Tennis Center on September 13, 2015.
Leonardo DiCaprio and Kelly Rohrbach attend the Men’s Final on day 14 of the 2015 U.S. Open at USTA Billie Jean King National Tennis Center on Sept. 13, 2015.

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As Us Weekly previously reported, DiCaprio and Rohrbach split in January after several months of dating. “They both have intense work schedules and a lot going on in their lives right now,” a source told Us at the time. “They both needed to take a break because of that. They are still friends and talking but it’s over.”

Leonardo DiCaprio attends the 88th Annual Academy Awards.
Leonardo DiCaprio attends the 88th Academy Awards.

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He’s been linked to Irish TV star Laura Whitmore and Rihanna since his breakup with Rohrbach, but DiCaprio is currently living the single life. However, that doesn’t mean he’s opposed to settling down in the future.

“That time will come when that time comes,” he told Parade magazine earlier this year. “The truth is, you can’t predict marriage. You can’t plan it. It’s just going to happen when it happens.”

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