Thanks to the absolutely stunning The Revenant, it is now almost a forgone conclusion that Leonardo DiCaprio will finally take home an Oscar. While many seem to cry foul that he has not already won the top accolade for his acting, truth be told over the course of his five nominations he has always come up against someone who has done something special – be it historical, career defining, or otherwise.
2014 saw his closest race against a completely transformational weight-losing effort from Matthew McConaughey in Dallas Buyers Club . In 2007 DiCaprio chose not to compete against his The Departed co-star Mark Wahlberg and was instead nominated for Blood Diamond, taking on Forest Whitaker’s role of a lifetime as Ugandan dictator, Idi Amin, in the almost forgotten (but very good) The Last King of Scotland. 2005 saw DiCaprio’s second collaboration with Martin Scorsese and in the process filling the shoes of his idol Robert De Niro as Scorsese’s muse in The Aviator. Yet Jamie Foxx was incredible in another historical biopic as blind musician Ray Charles in Ray. Finally there was his breakout role in 1994’s What’s Eating Gilbert Grape, where DiCaprio lost to veteran Tommy Lee Jones in the seminal 90’s thriller, The Fugitive.
However, you don’t get the sort of constant discussion every time Oscar season comes around that DiCaprio does without posting a great body of work. So before DiCaprio likely becomes 1 win from 6 nominations (and if you consider Al Pacino is only 1 from 7 with a body of work that includes The Godfather 1 & 2, Serpico, Dog Day Afternoon (rated as by the AFI as the 4th greatest performance ever), and … And Justice For All to name but a few) let’s look back at the performances that have made him a perennial contender.
10: Blood Diamond – 2006
Some liked the accent, some didn’t, but Blood Diamond saw a shift in DiCaprio’s on screen presence. Filling out and shedding the baby faced look, Danny Archer allowed DiCaprio to play self serving and treacherous – not fundamentally good nor bad, just a man making the best of the world he lives. The result was a wild, thoroughly entertaining ride through Africa. Blood Diamond and fellow 2006 film The Departed started an incredible run of actor/director partnerships and performances that would help build DiCaprio’s body of work to where it is today. The film saw his raw performance nominated for the Best Actor Oscar once more.
9: The Aviator – 2004
In his second collaboration with Scorsese, DiCaprio plays famed filmmaker and airline tycoon – Howard Hughes. The film won five Oscars, yet somehow has not really carried with time. That being said DiCaprio gets his first real taste of playing the ‘man teetering on the edge’ character he seems to be forever drawn to. Hughes was a flawed genius suffering from Obsessive Compulsive Disorder (OCD). The role gave DiCaprio a chance to flash his leading man charisma while also taking the audience into the frustration that Hughes felt every time an episode of OCD came on. The Aviator also brought his second Oscar nomination, and first since 1994.
8: Shutter Island – 2010
DiCaprio and Scorsese’s fourth collaboration brought Scorsese the best opening weekend figures of his illustrious career. The film went untouched by Oscar voters, but fans loved it. DiCaprio gives an emotional and caged performance as Teddy Daniels, a man besieged by guilt and teetering on the edge of his sanity. The film marked the first of two occasions in the same year DiCaprio would play a widower haunted by the wife he has lost (Inception is the other). Shutter Island is in many ways a throwback to earlier thrillers (such as Silence of the Lambs), but if it were not for the racing-against-the-clock performance of DiCaprio, the film would’ve fallen flat. It is also the first film on this list with an ending that kept audiences arguing over the fate of DiCaprio’s character.
7: Inception – 2010
This sci-fi-action-blockbuster showed that if done correctly the genre could have as much feeling as any drama-based film. In a much more paired back performance, DiCaprio also shows off his mastery of the acting craft. His character is the emotional heart of the film. Without a strong performance connecting the action to the drama, Inception would have been just another action piece of sci-fi action, yet without showiness DiCaprio makes us yearn for him to return to his children. Inception is of course the second film where DiCaprio plays a widower; further paralleling Shutter Island is an ending that left many, many audience members arguing what to make of it.
6: Django Unchained – 2013
The story goes Quentin Tarantino told DiCaprio if he didn’t take the character all the way, to as vile as he could be, the audience would never forgive him – and so he did. Django Unchained antagonist Calvin Candie was a huge departure from any other character DiCaprio had played before. Candie is entirely unlikeable, sociopathic, moronic, and DiCaprio’s first truly bad guy. DiCaprio plays Candie’s ignorance superbly as he struggles to make sense of the world around, an inability that sees him strike out in cruel acts of rage to assert his position. There are many infamous scenes, from the brutal dog mauling a slave scene (where some fool suggested DiCaprio requested the actor actually be killed for authenticity) to the dinner table showdown. DiCaprio was so in character during the scene he sliced his hand open on a glass but continued on as his blood poured across the table.
5: What’s Eating Gilbert Grape – 1993
What’s eating Gilbert Grape? Well, quite a lot really from his obese mother who can’t leave the house to caring for his autistic little brother Arnie (DiCaprio), and that is where the film gets interesting. Long forgotten by now, What’s Eating Gilbert Grape? is memorable for two reasons, one it’s the only time DiCaprio has ever shared the screen with Johnny Depp, and two it netted him his first Oscar nomination of his career. Not a bad feat in only your second major role. DiCaprio is quoted as saying, “Playing Arnie is the most fun I’ve ever had” – this was perhaps until Jordan Belfort came along. It’s testament to DiCaprio’s performance that the role was enlarged from being on a small one to a much larger one. Furthermore, director Lasse Hallstrom sacrificed part of her salary to pay for (at the time) the unwanted DiCaprio such was her belief in him.
4: The Departed – 2007
Reuniting DiCaprio once more with Scorsese and his The Basketball Diaries co-star Mark Wahlberg, while adding DiCaprio’s other idol in Jack Nicholson could only ever have of worked. And it did. In a remake of Hong Kong film Infernal Affairs, DiCaprio plays an undercover cop searching for Matt Damon’s rat, posing as a cop. The film finally won Scorsese (who should have had about four by this time) the Best Director Oscar, as well as a host of other nominations, but none for DiCaprio. Apparently the great man elected to be nominated for Blood Diamond instead as to not run against his co-star, Wahlberg. The film is wild, thrilling, and fun showcasing DiCaprio’s ability to go from masculine to vulnerable and on the edge. It is a joy to get to see DiCaprio share so much screen time with a man he clearly admires in Jack Nicholson, in what will likely be Nicholson’s last great film role.
3: The Basketball Diaries – 1995
Anyone who ever questioned DiCaprio’s acting ability early as he rose to fame on the back of blockbusters such as Romeo & Juliet (1996) and Titanic (1997), only had to go back to 1995’s The Basketball Diaries. Based off the autobiography of poet/musician Jim Carroll, the film is a no holds barred look at kids descent into the harrowing world of heroin addiction. This is the ultimate don’t do drugs movie that sees a group of friends go from promising basketballers and adolescent hell raisers to homeless junkies only wanting the next hit. The film also courted controversy due to a scene where DiCaprio dreams of gunning down teachers and students at his Catholic high school. The final scene between DiCaprio’s character and his mother will break your heart, and shows an incredible emotional range for an actor of such a young age.
2: The Revenant – 2015
The one that he finally won the Oscar for, DiCaprio leaves nothing behind as he claws his way across the uncharted wilderness of the 1800’s post a bear mauling to hunt down his Inception co-star Tom Hardy. The film is epic, on every level; the bear attack alone will leave many shaken. The cast and crew apparently suffered heavily in the cold conditions for their art, and in a further showing of the lengths Leo will go to for perfection the vegetarian ate raw bison liver as the script demanded. It would be very hard to see him not walking away with an Oscar this year.
1: The Wolf of Wall Street – 2013
It’s all about range. That’s what separates the Brando’s, De Niro’s, and Pacino’s from the rest – elevating them to cinema immortality. And in the three-hour story epic of excess DiCaprio gets to display just about his entire range – from dramatic to the previously unseen comedic. While he does not have the emotional depth of Brando, the transformational ability of De Niro, or the simmering rage of Pacino, DiCaprio does have a master’s control of his craft . The film gave DiCaprio a chance to show off his ability to be funny, furious, charming, smart, handsome, and genuinely fucked up. For a man who claims he has never done drugs, he sure does one hell of a job making us believe he’s high as a kite. DiCaprio’s performance doesn’t miss a beat as he spans generations in the shoes of infamous stockbroker and criminal, Jordan Belfort.