From child star to Oscar winner, DiCaprio’s career thrives – but his dating habits spark debates. Photo / Mary Cybulski
From child star to Oscar winner, DiCaprio’s career thrives – but his dating habits spark debates. Photo / Mary Cybulski
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.
Baby-faced DiCaprio first came to wider public attention aged 16, playing the troubled adolescent Garry Buckman-Lampkin in network sitcom Parenthood. Though the show only lasted one season, his intense performance was lauded – and it didn’t hurt that this camera-ready cutie had shiny blond hair, an adorable cheeky grin and, for a hint of edge, could rock a combat jacket. Leo the child star was born. He went on to star in Growing Pains in the role of homeless teenager Luke Brower.
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DiCaprio was critically acclaimed for his vivid turn as the mentally disabled Arnie in Lasse Hallström’s movie What’s Eating Gilbert Grape. At the premiere, accompanied by his more rock ‘n’ roll co-star Johnny Depp, he still had a fumbling youthfulness, but his increasingly cool hair was styled in classic 90s boyband-esque curtains. Watch out, ladies …
Leonardo DiCaprio earned his first Oscar nomination at 19 for What’s Eating Gilbert Grape. Photo / AFP
Leo the teenage pin-up
At the Oscars (1994)
DiCaprio scored the first of his six acting Academy Award nominations for What’s Eating Gilbert Grape and cemented his newfound Hollywood stardom by walking the Oscars red carpet in a classic tux – albeit still holding on to his youth by leaving his hair flopping over his forehead and eyes. A canny choice: millions of fans would soon be swooning over those locks as they pinned posters to their walls.
Romeo + Juliet (1996)
DiCaprio became a true leading man and romantic hero when he starred in Baz Luhrmann’s eye-popping, punk-rock version of Shakespeare’s Romeo and Julietfor the MTV generation. Here he is the modern knight in shining armour (and his maturing body fills out said armour very nicely), but also, crucially, a giddy kid utterly smitten with Claire Danes’ angelic Juliet, so retaining that boy-nextdoor accessibility.
Leonardo DiCaprio's role in Romeo + Juliet turned Shakespeare into a hit for the MTV generation. Photo / Century-Fox, Getty Images
Titanic (1997)
James Cameron’s juggernaut of a disaster movie turned DiCaprio into one of the world’s biggest stars, and won him the hearts of countless weeping girls. Cameron kept his essential teen idol appeal (his hair still effortlessly flops and he’s swamped by that dark overcoat), but Leo the serious – and sexy – actor was also starting to emerge in Titanic, particularly in his smouldering scenes with Kate Winslet.
DiCaprio became a global heart-throb thanks to Titanic, which remains one of the highest-grossing films of all time.
The Beach (2000)
DiCaprio just couldn’t stay out of the water. For thriller-meets-travelogue movie The Beach, however, he was sunning himself in Thailand rather than freezing in the North Atlantic, which meant his besotted fans got to see their boy all grown up and in swimwear, showing off his chiselled, bronzed torso and – gasp! – newly shorn, choppy, post-Titanic hair.
Leonardo DiCaprio at the press conference for 'The Beach' at the Berlinale 2000/50th Berlin International Film Festival in the Berlinale Palast. Photo / Frederic Kern, Geisler-Fotopress, AFP
Leo the Heart-throb
Catch Me If You Can (2003)
Steven Spielberg’s jaunty crime caper Catch Me If You Can required DiCaprio to convince as the charismatic con artist Frank Abagnale jnr, who seduces numerous women in the movie – and, infamously, hides from his police pursuers in a bevvy of gorgeous air stewardesses. The actor recreated that scene at the premiere in a real heart-throb power move, while also unveiling his moody new look: tamed locks, a dusting of facial hair and a sleek black suit.
Catch Me If You Can. Photo / AFP
With Gisele at the Oscars (2005)
DiCaprio is now known as a serial dater of (young) models – an increasingly desperate look. But he could still pull it off when, as a handsome thirtysomething, he took then-girlfriend Gisele Bündchen to the 2005 Oscars, having been nominated for The Aviator. Sensibly Leo kept it simple with his well-cut, if somewhat funereal dark suit, knowing that practically all eyes would be on his gorgeous supermodel date.
Leonardo DiCaprio and Gisele Bundchen at the 77th Annual Academy Awards. Leo was nominated for Best Actor in a Leading Role for The Aviator. He didn't win. Photo / Getty Images
The Departed, with Matt Damon (2006)
Can DiCaprio do tough guy? Not really, but in The Departed he diversified his image somewhat by playing the undercover cop trying to infiltrate the mob. Matt Damon, as his parallel character – the mob spy in the police – was much more convincing: here Damon does have some street cred, while denim-clad DiCaprio could have wandered out of a Gap ad (the facial fuzz really doesn’t help).
The Departed, with Matt Damon. Photo / COOPER and Plan B Entertainment, Initial Collection, Christophel, AFP
With Bar Refaeli
DiCaprio’s next dip into the model pool came with Israeli blonde beauty Bar Refaeli. Like his romance with Bündchen, the relationship lasted several years, and candid snaps made him a tabloid fixture – though still a lusted-after one. But it did feel increasingly at odds with his more serious professional aims.
Leonardo DiCaprio and supermodel Bar Refaeli attend a game between the Orlando Magic and the Los Angeles Lakers in 2010. Photo / Getty Images
Leo the Oscar chaser
The Wolf of Wall Street (2013)
One golden figure still eluded DiCaprio: that Oscar statue. As he neared the end of his 30s he went after it hard, scoring another nomination for his gonzo turn as drug-inhaling finance bro Jordan Belfort in Scorsese’s The Wolf of Wall Street. That Don Draper look was also a great one for DiCaprio as he entered this new phase: the slicked-back, darker hair, pinstriped suit and sleazy confidence.
Leonardo DiCaprio as Jordan Belfort in The Wolf of Wall Street. Photo / Mary Cybulski
Toni Garrn
Alas, there appeared to be much less progress in DiCaprio’s personal life – in fact, as the years passed, he seemed frozen in time, still dating blonde models in their 20s. That disparity became more apparent with each unflattering paparazzi pic. Playing volleyball with bikini-clad German model Toni Garrn during the Fourth of July weekend, he looked tired and paunchy in a white T-shirt, and his long hair and massive beard aged him further.
It was the bear that won it. Finally, in his most naked attempt yet, DiCaprio scored his Best Actor Oscar for harrowing survival drama The Revenant, in which he played a 19th-century frontiersman. Perhaps it took this complete erasure of his radiant handsomeness for Oscars voters to take him seriously (or at least that’s what he believed) – there’s definitely no trace of the heart-throb in his gaunt physique and straggly hair.
The Revenant required DiCaprio to eat raw bison liver for authenticity, earning him his long-awaited Oscar.
DiCaprio appeared not to take his Oscars triumph as a sign to start graciously maturing into a Hollywood silver fox à la George Clooney. Instead, he paired up with – you guessed it – yet another model, Camila Morrone (23 years his junior). Their Italian holiday snaps made for grim viewing, the sexy Morrone in a barely-there leopard-print bikini a stark contrast to slouching, pudgy Leo in a pulled-down baseball cap.
DiCaprio seems to have a much better handle on the ageing process when he’s on the big screen. Losing his youthful good looks has freed him up to play not just the usual leading man fare but more offbeat (and nefarious) character roles too, such as the greedy, witless Ernest in Scorsese’s Killers of the Flower Moon. He sported his most unflattering, greasy haircut to date for the role, plus yellowing false teeth.
Robert De Niro stars in Killers of the Flower Moon as the villainous Bill Hale. Killers of the Flower Moon marked DiCaprio's sixth collaboration with Martin Scorsese. Photo / Apple TV+
Vittoria Ceretti (2024)
As he turns 50, DiCaprio has unfortunately gone from adored, handsome pin-up to total embarrassment. Pictured with his latest fling, Italian model Vittoria Ceretti (aged 26) on holiday in Sardinia, he looked more like her cringe-worthy dad than her boyfriend – complete with awkward dad bod, hideous mid-length hair (a sad version of his boyish floppy locks), and a morning-after scruff of stubble. DiCaprio is ageing very disgracefully.
Italian model Vittoria Ceretti, 26, is the current girlfriend of Leonardo DiCaprio, 50. Photo / Etienne LAURENT, AFP
