Five times Leonardo DiCaprio should’ve won an Oscar

After countless performances in extraordinary films it looks as though it could finally be Leonardo DiCaprio’s year for clinching that Academy Award win. The nominations are in and The Revenant leads in 12 categories with DiCaprio up for Best Actor. The thespian is the talk of the town after his win at the Globes recently and his nom announced today, but why are we always so fascinated by this man and his performances during awards season? Simply put, he’s been robbed time and again. DiCaprio isn’t the only actor to of missed out on his deserved trophy but he’s a recent example of a once-in-a-generation talent who should have won more than one Oscar by now. Forever channeling a raw emotion – and never playing the same man twice – here are the characters the actor won us all over with. Don’t worry Leo, in our hearts and minds you’ve had the Oscar plenty of times.

Shutter Island (2010, Martin Scorsese)

Shutter Island was a change in direction for both director Scorsese and actor DiCaprio. A psychological thriller that had moments of horror, the film was a hit with critics and audiences and stayed imprinted in the mind following the atrocities sen on-screen. As the visually disheveled and slowly crumbling detective Teddy Daniels, DiCaprio was as never before seen in an emotionally-draining and physically exhausting role. There is a genuine mastery that DiCaprio deploys as Teddy, an aging man who is slowly but surely losing grip of the reality around him. Despite his character flaws and his total, mental unraveling, you can’t help but still hope it will all be alright in the end. Of course, in a Scorsese film, it never is.

The Basketball Diaries (1995, Scott Kalvert)

The film itself is a bit of a shitter and it didn’t fare so well among critics. Telling the story of poet and ex-junkie Jim Carroll, Kalvert’s feature has one saving grace: Mr DiCaprio. The actor was undergoing the transition of child star to serious adult talent at the time and doing his indie bit, it’s basically a tradition for all big industry names. As Jim, the actor embodied gritty and unlikable character traits while possessing an adolescent naivety as his life becomes consumed by heroin. It’s a tough film and a truly brave role to of undertaken at such a pivotal point in his career. From prostitution to burglary, Carroll went through it all before finally going to prison and getting clean – and the film doesn’t put a glossy cinematic sheen on any of it. DiCaprio showed then what he still shows now: a complete and impenetrable on-screen power.

The Departed (2006, Martin Scorsese)

By this point DiCaprio and Scorsese were serious filmmaking pals. Having previously teamed up on Gangs of New York it was obvious that the duo were on a journey to cinematic perfection together. They found that perfection some-when in 2006 with the utter genius of The Departed. Violent, intelligent and with a claustrophobic city ‘scape that’s still magnificently fresh on the eyes, the feature was the flick to finally nab Scorsese the Best Director Oscar. Unfortunately the same can’t be said for DiCaprio. Of all of the nods the actor has had, many argue it should of been Billy Costigan that clinched it for him. He’s at his best when his characters are experiencing emotional turmoil (sorry, Leo) and that trait is seen in such an inventive and prevalent way here. One minute Billy is beating up mobsters and seemingly untouchable, the next he’s cracking up in a shrinks office talking about his non-existent shaking hand. Every step of the way Leo toys with his source material, surprising his audience at each moment – you are never really sure if you should be concerned; as Billy he is unreadable, a complete closed-book that you constantly want more of.

leonardo dicaprio and ray winstone in the departed

leonardo dicaprio and ray winstone in the departed

Django Unchained (2012, Quentin Tarantino)

Quentin Tarantino’s dive into slavery was pretty much universally beloved. Leonardo DiCaprio as a cotton farm antagonist was universally feared. Now famously remembered for accidentally cutting his hand, continuing to film, and creating the best scene in the entire feature, Calvin Candie was a move to a role he had never previously focused on. As the villain of the piece Leo had fun; he was smarmy, strangely witty and damn-right hated, three characteristics that only DiCpario could encapsulate with such ease. Worryingly, he was also slightly sexy (don’t overthink it).

What’s Eating Gilbert Grape (1993, Lasse Hallstrom)

What’s Eating Gilbert Grape was Leo’s third movie role, and one that saw him play a character who has a developmental disability. There is a thin line between carefully handled and undeniably insensitive with parts like these and DiCaprio never seems to forget that. He works with his source material incredibly tentatively, especially for such a young actor as he portrays Arnie, an innocent adolescent who grabbed the hearts of his audience and wouldn’t let go until 118 minutes later. It’s one of the roles that isn’t widely seen but it deserves recognition; this isn’t the actor that we have all come to know now – you know, the one who stars in thought-provoking and genre busting features. This is a rising star who’s on-screen prowess can truly – and so purely – be seen on-screen for the first time. This is a portrayal of innocence that can’t be tainted.



Leonardo DiCaprio – top three performances

Leonardo DiCaprio (middle name Wilhelm for a little bit of trivia – and who doesn’t love how fierce that is?!) has been in twenty five features, nominated for an astounding ten Golden Globe’s and four Oscars – coming away with no wins for the latter which has often raised questions as to why. Known for playing an array of now cult characters – from the obvious Jack in Titanic to con artist Frank in Catch Me If You Can and Romeo in Baz Luhrmann’s daring adaption of the Bard’s classic story of forbidden love. Whatever the role – DiCaprio has pretty much always aced it, having worked with directors such as Spielberg, Nolan, Eastwood and Boyle. Ignoring the fact the Academy cant recognise this talent with that Best Actor trophy, the number of auteur’s who have happily worked alongside the actor and the sheer number of projects he’s taken part in that have received both critical and commercial acclaim validates that DiCaprio is at the top of his game. Here, I have selected three films (it was originally five but that spiraled out of control) that epitomize this talent, stand alone as movies of great worth, and exemplify DiCaprio’s love of taking on diverse roles.

1. William Shakespeare’s Romeo + Juliet Baz Luhrmann, 1996

Luhrmann has now cemented himself as a director full of quirks and plenty of eccentricity. Romeo + Juliet was only his second feature (and part of his ‘Red Curtain’ trilogy along with Strictly Ballroom and Moulin Rouge) and verified the guy as someone will plenty of vision (that MTV aesthetic is a winner every time) and an eye for talent. Casting Clare Danes and our man DiCaprio in the lead was a smart move and saw the pair quickly go on to roles in mainstream films that caught the eye of directors such as Martin Scorsese – who DiCaprio has now worked with on five features.

Luhrmann was the first to bring old-school Shakespeare to the contemporary, artistically swapping swords for guns and Verona for Venice Beach – keeping the classic dialect and bringing in an accompanying soundtrack of Radiohead and The Cardigans to match the woeful script. Dicaprio and Danes carry the whole feature but its the formers performance as the intense, boyish and naive Romeo that stands out. The brilliance of the actors performance is in his understanding of the Bard’s words; this coupled with the emotion poured into the role brings meaning to an era

dicaprio as romeo in baz luhrmann's film

dicaprio as romeo in baz luhrmann’s film

of writing that seemed to get lost in school classrooms.

The chemistry between Danes and DiCaprio is electric and the pure realism of the pairs romance is palpable but Luhrmann is careful to never undermine the raging family war that is at the heart of this story. John Leguizamo provides support as Tybalt, and the poignant scene in which the two feuding families come to a head determines the strength of stylized cinema if supported by an ensemble cast capable of giving enough – and this is clearly seen here. Undeniably underrated but damn near perfect, Lurhmann’s feature exemplifies DiCaprio’s ability to transcend the feeling of traumatic love and deep emotion to a new generation of people who quickly became versed in the ways of Shakespeare.

2. The Basketball Diaries – Scott Kalvert, 1995

The Basketball Diaries is probably one of Leo’s least know roles. Daring, Provocative and heavy on real-life topics, Kalvert’s film plays with surreal dreams and hard-hitting reality to successfully convey the early life of drug-addict turned poet Jim Carroll. An indie flick and released in 1995, DiCaprio took a risk so early on in his adult career portraying Carroll who went to extreme lengths to attain drugs (some of which are acted out on screen and define the word gritty). Not necessarily praised by critiques upon release, this 90’s drug drama has achieved a kind of cult status which is certainly deserved.

mark wahlberg and dicaprio in the basketball diaries

mark wahlberg and dicaprio in the basketball diaries

The reason – out of so many performances to chose from – this is my number two for Mr DiCaprio is because of the sheer power of his brutal performance. Adolescence and rebellion is truly captured with Jim, as he navigates growing up, tailoring his skill as a writer, and urban life in New York city. Kalvert’s film and DiCaprio’s representation of a teenager destroyed by drug abuse pulls no punches and expects the same from those watching. This is no fairytale rendition of the highs and lows of coming of age but it is an intelligent retelling of a mans fight to overcome the temptation of drug use.

Leo was only 21 when he shot The Basketball Diaries and at such a young age managed to present himself as an actor unafraid to take a gamble. Heart-wrenching in it’s honesty and a great feature that shows us a young Dicaprio doing his time on the indie scene but about to take the rest of the world by storm.

3. The Departed – Martin Scorsese, 2006

Martin Scorsese won his first Best Director Oscar for this nostalgic gangster flick. Casting DiCaprio as troubled undercover cop Billy, the director recaptured the spirit of this beloved genre of film; successfully channeling classic features such as Goodfellas. In this role, DiCaprio shone as an actor now well into his career as an adult talent on the Hollywood scene – away from the romantic dramas of the 1990’sSince The Departed, he has continued to involve himself in a number of violent films which challenge the minds and eyes of those watching.

dicaprio as billy in the departed

dicaprio as billy in the departed

Scorsese’s Oscar winning film reiterates the strength and power of the emotion constantly packed in to any given character Leo can get his hands on (apart from ‘Wall Street perhaps), and as a Southie resident who takes part in a number of violent endeavors, Billy is as loveable as a gangster can possibly be. As cliched as the genre can sometimes be, DiCaprio is sure to shy away from giving a formulaic performance and is able to give an underlying representation of a contemporary hyphenated male struggling with his masculinity in a socially divided America.

There are so many more incredible performances to pick from but these three represent pivotal moments in the actors career as he strove to obtain acting perfection.