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Leonardo DiCaprio Shares an Embarrassing Link With Taylor Swift – and Fans Are Only Realizing It Now

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Published On: September 25, 2025
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Taylor Swift and Leonardo DiCaprio
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Leonardo DiCaprio has recently made a historic revelation when he appeared on the New Heights Podcast. The Academy Award-winning star chatted on the podcast with Jason and Travis Kelce. The icon, who is 50, claimed that his conversation with the cinephile brothers marks his debut in the world of podcasts. The episode that aired on Wednesday, and overlooked, his 2020 appearance with Brad Pitt on Marc Maron’s WTF podcast, which discussed Once Upon A Time In Hollywood.

In the latest New Heights episode, Leonardo was with his One Battle After Another co-star Benicio del Toro. They deeply discussed cinema and actors with the Kelce brothers. The episode became sensational when Jason Kelce commented on Travis’ fashion choices.

However, viewers noted that no one in the podcast talked about Taylor Swift. Travis, who got engaged to the pop sensation last month, often talks openly about his romance. He even discussed his wedding preparation updates with his brother on the weekly show.

The bride-to-be shares a minute connection with Leonardo, and we are referring to the 2019 album, Lover. On one of the songs, The Man, Taylor sings about what being a male celebrity would feel like, and she refers to Leonardo DiCaprio. The opening lines say, “I would be complex, I would be cool,” reports The Mirror.

Taylor mainly discusses the disparity that men and women feel in the world and the contrasting standards. Especially when it comes to their private and romantic relationships, female celebrities often face brutal media attention.

Similar to Taylor, Leonardo has maintained numerous high-profile romances throughout his career in the spotlight, typically with younger women. But the difference lies in the fact that the Shutter Island actor never had to face the sexist criticism Taylor had to endure. The media and public have often been misogynistic in their approach towards female celebrities, and this incident is no different.

In Taylor’s 2019 tracks, she writes, “What’s it like to brag about drinking and dollars and getting [expletive language] and models? … If I was out flashing my dollars, I’d be a [expletive language] not a baller / They’d paint me out to be bad / So it’s okay that I’m mad.”

Taylor then confidently talks about this one popular celebrity as an example. She screams, “And they would toast to me, oh, let the players play/I’d be just like Leo in Saint Tropez.”

She even went a step forward and morphed herself into a male persona for her 202o music video. In the opening scene, the male version of Taylor appears in an office where she gazes out at the urban landscape, and any pop culture madhat would understand the not-so-subtle reference to Leonardo’s most iconic movie, The Wolf of Wall Street.

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Shrobana Rakshit

Shrobana is a passionate writer and feminist who believes in the power of words to challenge social norms, shatter glass ceilings, and inspire change. She is in constant need of coffee and fresh nutrition for her brain. You’ll often find her in the corner reading Arundhati Roy and planning her next Instagram post. She is a certified Lana Del Rey fangirl with an immense love for writing on pop culture. Now, she gets to live her dream every day and couldn’t be happier.

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