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While the career of Hollywood’s golden boy went stratospheric, his pattern of dating twentysomething models isn’t quite so alluring Is Leonardo DiCaprio feeling like the King of the World since he turned 50 on November 11, or does the Titanic star feel he’s hit a middle-aged iceberg? His career is still flourishing: he finally notched up that Oscar win for The Revenant in 2016, and he remains the star of choice for revered directors such as Martin Scorsese. But in other ways, Leo is ageing pretty disgracefully. Instead of finding a silver-fox look and embracing a mature relationship, he’s clinging on to his youth by wearing grungy baseball caps and unflattering T-shirts, and continuing to date twentysomething models – who are now half his age, a deeply unattractive look.

Here is how Hollywood’s golden boy went from teen pin-up to cringe-worthy dad bod. Leo the child star.

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