13 years’ worth of Leonardo DiCaprio in 6 must-see movies

Leonardo DiCaprio has been in showbiz for over 30 years and we’ve seen him go from baby-faced tween to handsome leading man. If you’re streaming savvy, you can literally watch the 46-year-old age by streaming these movies in chronological order.

Leo’s age: 32

Set in 1999 in Sierra Leone, the movie follows Leo’s character, Danny Archer, a rough-around-the-edges mercenary from Zimbabwe (which is still called Rhodesia in the movie). He’s a wheeler-dealer conman who fought in the South African border war and knows how dirty the real world can be – and he’s seen it too: he was thrown in prison for smuggling diamonds.

And that’s where life comes full circle – he hears gossip about a giant pink diamond and plans to get his clutches on it, sell it to the highest bidder and escape from Africa. Using his contacts, Archer finds Vandy (Djimon Hounsou), a fisherman with links to the diamond, but it’s not going to be easy getting the gem: Archer and Vandy aren’t the only people who want it…

Leo’s age: 36

This sci-fi film from Christopher Nolan (he wrote, produced and directed it) sees Leo play criminal Dom Cobb, who specialises in breaking into people’s minds and stealing their thoughts. He’s known as an extractor – using ultra-secret tech, he “shares” dreams with his victims and is part of an industrial espionage team.

Stealing dreams is one thing, but it’s a whole other matter implanting thoughts into someone’s head. And that’s exactly what Cobb and his team are hired to do by a tech giant who’s determined to beat his competitor by any means necessary. What is spurring Cobb on to try this near-impossible mission? If he succeeds with the “inception” process, his criminal record will be erased and he will be able to return to his home and family.

Leo’s age: 38

It’s not every day that Leo plays a villain, but when he does, he is mesmerisingly evil and easy to hate! In this revisionist Western flick by Quentin Tarantino (they’ll team up again – keep reading), Leo plays Monsieur Calvin J Candy, a plantation owner with a penchant for forcing his slaves to fight to the death in violent brawls.

Calvin is at the centre of the story because he owns Broomhilda (Kerry Washington), the wife of lead character Django (Jamie Foxx), who wants her back. It’s not just the fact that Calvin is, one, a slave owner, and, two, forces his slaves to murder each other, he’s just a really horrible guy. He’s pretentious, smokes cigarettes in those fancy holders so his fingers don’t get stained, he takes pleasure in others’ misery, and he thinks because he’s got money he’s king of the world. So seeing him get his comeuppance is the icing on the cake.

PS: the scene where Calvin bangs his hand on the dinner table, Leo really did cut himself – that’s his real blood pouring out his hand and because he stayed in character, Quentin kept filming and kept it in the final edit.

Leo’s age: 39

F Scott Fitzgerald’s 1925 novel comes to life in glitz,y glamorous fashion, set in the roaring 20s. Leo plays suave businessman millionaire Jay Gatsby, who’s known for his extravagant parties. He befriends his wannabe-author neighbour Nick Carraway (Tobey Maguire), who narrates the movie (it’s his novel and life story). They have a connection, though – Nick’s married cousin Daisy (Carey Mulligan) was the woman Gatsby fell in love with while he was in the army.

And, in fact, he’s still in love with her – it’s revealed that his notorious parties are thrown for the sole purpose of getting Daisy to his house. While he’s the host, Gatsby almost never enjoys his own events because his one true love never arrives.

But after discovering their connection, he uses Nick to get to Daisy and they fall in love again, with Daisy wanting to ditch her abrasive hubby Tom (Joel Edgerton) and run off into the sunset with Gatsby and live happily ever after.

Leo’s age: 39

This biographical drama is probably the wildest thing Leo will ever do… and it’s all real. He plays Jordan Belfort, a small-time stock broker who hits the jackpot with a pump-and-dump scheme. He and his business partner Donnie Azoff (Jonah Hill) buy stock on the cheap, hype up the brand through “misleading media representation” (that’s a nice way of saying “they lie through their teeth and make the stock seem amazing”), then sell for a huge profit. The thing is, Jordan is wild and loves the life of excess – everything he does has to be big and flashy and fancy, from cars and homes to drugs, parties and women.

But while Jordan is going wild with his millions, the FBI and SEC federal agencies are quietly digging into his company, Stratton Oakmont, in search of the tiniest piece of evidence of wrongdoing. The only thing that the real Jordan Belfort didn’t like about the film was that it made his scheme look “cruel and malicious, that I was just trying to rip people off”.

Leo’s age: 45

What you need to know: this Quentin Tarantino movie is a mix of fictional and real-life people – for example, Rick Dalton (Leo’s character) is based on Steve McQueen, while Bruce Lee (played by Mike Moh) is real. The events are entirely fictional.

Leo takes on the role of Hollywood hotshot Rick Dalton, whose career is tailing off in 1969 where he’s no longer the leading man in big-screen blockbusters and is left picking up crumbs as a bit-part villain. Like most Hollywood stars, the fear of losing his fame and fortune weighs heavily on Rick and he’s desperate to keep shining, even if it means begrudgingly taking jobs working in Spaghetti Westerns, cowboy films made in Italy.

At the same time, Rick has to deal with his moody and broody stunt double and chauffeur Cliff Booth (Brad Pitt), whose world is imploding thanks to his stand-offish nature, his stubbornness and the fact that everyone thinks he murdered his wife. On top of that, Rick’s new neighbour moves in – movie maker Roman Polanski and his actress wife Sharon Tate – and they’re targeted by the infamous Manson Family, a group of brainwashed acolytes who were instructed by deranged cult leader Charles Manson to commit murders.