Anguish level: 1. Cool as ice
Jack Dawson (Titanic, 1998)
Our hero looks pretty chilled for a guy who’s about to bid bon voyage to life, even if Jack’s about to look a whole lot cooler thanks to Rose’s ‘one-person per debris’ policy despite the obvious room for him to climb onto it as well. There’s a good reason for Leo’s grace under pressure though: Titanic might not have broken a whole slew of box office records if its dishy hero had carked his grundies on his way to the bottom of the ocean. Well, we would have let him on the raft anyway.
Anguish level: 2. Sedation required
Jordan Belfort (The Wolf of Wall Street, 2014)
It turns out that the drugs really do work. Exhibit A: This man is very, very upset. However the pressing problem that the FBI is about to invade his millionaire bankers-lifestyle has been somewhat nullified by the fact that the very strong Quaaludes he’s taken have just kicked in. Only Leonardo DiCaprio could turn banker Jordan Belfort, who’s a grade-A slimebag when he’s not a dribbling idiot, into a watchable rogue, almost making us complicit in his crimes as he rips off the vulnerable. We just have to hope the comedown really hurts.
Anguish level: 3. Exquisite
Jay Gatsby (The Great Gatsby, 2013)
Few things say ‘the churning pain hiding behind the glamour’ like an elegant single tear leaking down a perfect cheek. DiCaprio is ideally cast as Gatsby, the glittering life of the party who’s slowly dying inside thanks to his nostalgia-tinted love for the more clear-sighted (and now-married) Daisy Buchanan: the inevitable conflict between their two differing outlooks will send him to his grave – those that live in the past are doomed to stay there forever.
Anguish level: 4. Torn apart
Billy Costigan (The Departed, 2006)
“The other night I thought I was having a heart attack. I puked in a trash barrel on the way over here. I haven’t slept for weeks.” Having spent a year undercover while some of Boston’s most violent gangsters sniffed suspiciously around him, cop Billy is under a loooot of pressure and it’s started to blow a gasket in his head. Despite being surrounded by great actors with flashier parts, without DiCaprio’s compelling, desperate-eyed edge at its core The Departed’s devious knot would unravel rather quickly.
Anguish level: 5. Furious
Calvin J Candie (Django Unchained, 2012)
Things Calvin Candie likes: French things, slavery, Mandingo fights, winning. Things the hateful Monsieur Candie doesn’t like: people who try to trick him in his own Candyland estate. It makes him volcanically angry in fact, to the point where a frothing mad Candie offers his unruly houseguests an unwelcome lesson in the bogus, racist science of phrenology. DiCaprio slammed his hand down so hard on the table during this scene that he accidentally cut himself on a glass and just rolled with it, sploshing real crimson everywhere and earning himself a standing ovation from director Quentin Tarantino and the crew.
Anguish level: 6. D.I.V.O.R.C.E
Frank Wheeler (Revolutionary Road, 2008)
“You are an empty, empty hollow shell of a woman!” Take a ringside seat as the ‘special’ Wheelers’ marriage combusts in excruciatingly raw, bloody detail, made all the more painful when it’s Titanic-legends ‘Kate&Leo™’ throwing each other headfirst through the emotional wringer. DiCaprio here gives one of his most underrated performances as Frank, trapped by the ’50s conventions that he’s ultimately too profoundly boring to escape. You’ll need a stiff drink afterwards. Maybe leave the bottle too.
Anguish level: 7. Helpless
Arnie Grape (What’s Eating Gilbert Grape, 1993)
While some might find it hard to imagine a world where Leo wasn’t a global megastar, viewers coming out of Lasse Hallström’s gentle drama in 1993 were stunned that the 19-year-old newcomer playing the developmentally disabled Arnie Grape was just acting. The scene where Arnie discovers that his mother’s quietly passed away in her bed – slowly understanding that something’s not right – remains a devastating masterpiece of sensitively observed grief. No, I’m not crying, it’s just the June humidity sticking to my face.
Anguish level: 8. Grave
Hugh Glass (The Revenant, 2015)
It's not just a hairy encounter with a bear that's left Hugh Glass feeling grizzly: while incapacitated, he's also witnessed his only son be foully murdered, fuelling Glass with enough burning hatred to rouse himself back from the grave and send our hero on a grueling pursuit of vengeance, and maybe – finally – that Academy Award to boot. After all that method freezing-water plunging and raw liver-eating, Leo deserved something to cheer him up.
Anguish level: 9. Shakespearean
Romeo Montague (Romeo + Juliet, 1996)
Wherefore art thou Romeo? Well, he’s on his knees raging at the unjust gods, although to be fair, the lad has just found out that his beloved is occupying a fresh plot in the Capulet family crypt. Baz Luhrmann’s greatest asset was making sure his tragic star-crossed lovers genuinely look like they suffered from over-cranked teen hormones, with Leo transforming himself into a swishy, edgy heart-throb to make the girls declare that “I never saw true beauty 'til this night’.
Anguish level: 10. The nuclear meltdown
Teddy Daniels (Shutter Island, 2010)
Well, look at that face in all its puffy eyed, snot splattered, grief-etched glory. DiCaprio’s haunted US Marshall-with-a-secret Teddy Daniels has spent the whole of Shutter Island looking sweaty and uncomfortable and by the time you reach this crucial scene, you can finally understand why. It says a lot about the actor that by this point in his career that he now had the confidence to throw aside the cherubic baby-cheeked, pin-up image and just go full-on ugly cryface. Tissues for sad Leo, please.
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