Leonardo DiCaprio At 50: Secret Of The Peter Pan Of Hollywood’s Enduring Appeal

Part of Leo's appeal is that, despite his huge fame, he remains an enigma


by Jessica Snow |
Updated on

Gen Z has many things we don’t – TikTok literacy, open dialogue around mental health, an astute social conscience – but they will never fully comprehend why Leonardo DiCaprio remains the ultimate celebrity crush. To them he is an actor; to Millennials (and up) he is it.

To really get Leo – and for the DiCaprio devotees he is always just ‘Leo’ – you have to be old enough to have seen Titanic in the cinema on its release (11 times in my case; not an unusual feat at my girls’ school). Nothing will ever hit like seeing him standing at the bottom of the stairs on the doomed vessel in his tux. The late 1990s and early 2000s were a golden Leo age – see also his Hawaiian-shirted Romeo or his tanned, gap year turn in The Beach.

Now Leo has turned 50, meaning we are not that far behind and should definitely have grown out of our crush. Alas I, like many of my peers, remain inside the 13-year-old who dragged home a Leo-emblazoned 6ft tall ex-display board advertising the VHS release of Titanic from WH Smith.

But why is he it? Why is a new Leo film the one guaranteed way to get me and my pals back into the cinema (even if it is really, really long and about to drop on TV the next week – hello, Killers Of The Flower Moon – I don’t miss a Leo big screen opportunity). The appeal is not down to a supply shortage; there is no lack of handsome actors (Drew Starkey and Harris Dickinson have something of the Leo sparkle) or even nostalgic crushes to indulge in (see the Adam Brody-naissance).

Part of the appeal is that, despite his huge fame, he remains an enigma. Although off-duty the Leo look is slumbro/f**k boy-coded – baggy shorts, Dodgers caps, vaping indoors – he is simultaneously  very ‘old Hollywood’; untouchable and unknowable. He rarely gives interviews, he employs semi-successful disguises to evade the paparazzi and his Instagram profile is exclusively reserved for his environmental work. He is elusive. He’s not even done prestige TV.

And then there is the fact that although he is never exactly single, he is yet to ‘settle down’. Leo is a party boy at home in VIP areas, rolling with his lads – Jonah Hill and long-time bestie Tobey Maguire among them. It seems unlikely he will do a George Clooney and shake off his bachelorhood to settle down in his fifties.

He is a bad boy heartbreaker who you can harbour a secret (or not so) desire to change. Never mind that the ever-widening age gap between him and his model girlfriends (current beau Vittoria Ceretti is notably over 25… she’s 26) means that most of us are a decade-plus and a few dozen catwalk appearances away from ever executing that plan.

That mystique around Leo means that the work has to speak for itself – and he really is one of the best actors of his generation. Talent plus charisma? Oof, dangerous. Talent plus charisma plus nostalgia? Lethal!

And what beckons next? It’s tempting to align him with his hero, pal and one-time Scorsese-collaborator Jack Nicholson (of whom Leo also does an uncanny impression). Nicholson continued to take on interesting, exciting roles well into his sixties and seventies; similarly, Leo, who is next slated to star in Paul Thomas Anderson’s hotly-anticipated The Battle Of Baktan Cross, shows no sign of slowing down. Another similarity – they share the same cheeky, Peter Pan glint.

Happy birthday Leo, I love you.

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