Man at His Best

9 Movies With Leonardo DiCaprio That You Should Watch

Before he won an Oscar, Leo was already a crowd favourite with these roles.

BY editors | Feb 29, 2016 | Film & TV

Well before he won an Oscar, Esquire Malaysia’s March cover star has always been effortlessly chameleon-like in portraying these classic, crowd-favourite roles.

1 | Inception (2010)
What happens when you start messing with the physics of a Parisian dreamscape? In Inception, it folds up like a piece of toast as DiCaprio’s Dominick Cobb and architecture student Ariadne (Ellen Page) stare in wonder before embarking on a gravity-defying walk through this subconscious Paris of Cobb’s mind. You didn't want to look away, in case you missed an important moment in the plot.


2 | What's Eating Gilbert Grape (1993)
Critics widely agreed that DiCaprio should have won an Oscar for his role in Gilbert Grape. The movie is a look into the lives of 24-year-old Gilbert, a supermarket cashier, his morbidly obese mother and Arnie, his mentally challenged younger brother, portrayed by DiCaprio. Set in a sleepy Midwestern town, we follow the two brothers as they navigate heart wrenching twists and turns thrown at them.


3 | The Beach (2000)
A Leo classic that encapsulates the idyllic backpacker’s dream of finding paradise somewhere on earth. Who can forget the scene of Richard, Etienne and Francoise knee deep in sea water, gazing at an impossibly blue lagoon? We all wanted to be there with them.


4 | Shutter Island (2010)
A neo-noir psychological thriller based on Dennis Lehane’s novel of the same name. In Shutter Island, we see a pivotal moment when Teddy, who is “investigating” the goings on at a hospital for the criminally insane, poses the question: "Which would be worse—to live as a monster, or to die as a good man?" Very dark indeed.


5 | Catch Me If You Can (2002)
Few of us could help being charmed by the exploits of Frank Abagnale Jr, a not quite 18-year-old imposter who pretended to be a pilot, a doctor and a lawyer to con millions of dollars from unsuspecting victims. We were rooting for him to stay one step ahead of Tom Hanks’ FBI agent Carl Hanratty at every turn, and he had the best line in the movie: "You know why the Yankees always win, because they can't take their eyes off those pin stripes."


6 | The Departed (2006)
We considered a few favourite Departed scenes, including the elevator scene with Matt Damon’s bloody nose and Billy (Leo’s character) and Madolyn’s love scene, but ultimately we went with the rooftop faceoff between Billy and Colin. For good measure, you can compare the scene with the original Hong Kong flick Infernal Affairs, in this clip below:


7 | Titanic (1997)
Leo was thrown into heartthrob status for his portrayal of Romeo in the Shakespeare-adapted film Romeo & Juliet, but playing Jack Dawson cemented it for Hollywood eternity. Ask your lady if she was one of the legions who found herself faint of heart when he uttered the words, “You jump, I jump, right?” More likely than not, she will admit this to be true. And of course, that flying scene with Rose…


8 | Wolf of Wall Street (2013)
Intense best describes this movie. Outrageous parties, sex, drugs and alcohol fest, and Leo plays it up like he means it, snorting up white powder with dollar bills that he then crushes and dunks into the trash. Hard to believe such antics really do happen behind the scenes at Wall Street, yet we can’t help but watch and stare.


9 | Gatsby (2013)
There’s an element of lamb-to-slaughter in this movie that makes the scene where Jay Gatsby raises a martini glass to Nick the movie’s narrator,—and reveals himself as the host of all the lavish parties in a wealthy town on Long Island—all the more compelling. The cowardice and betrayal by Daisy, the object of Gatsby’s affection, contrasted against his own gallantry and hopeful naïvete play each other off, making this movie tragic in a bittersweet way.