A-Ron’s Film Rewind Presents: The Best Of Leonardo DiCaprio

Leonardo DiCaprio Is A Six Time Oscar Nominee & The Winner Of One For His Performance In “The Revenant”. From His Role In “Titanic”, DiCaprio Became A 90’s Heart Throb. Soon He Shook The Heart Throb Status & Became One Of Hollywood’s Most Phenomenal Actor’s. His Career Has Proven His Talents In Drama, Action, Comedy & Bio-Pics. This Weekend He Re-Teams With Quentin Tarantino For “Once Upon A Time In Hollywood”. I Have Ranked My Favorite & Best Films & Film Performances From DiCaprio’s Illustrious Career. 


#1: Wolf Of Wall Street – 2013

Legendary filmmaker Martin Scorsese directed this three hour bio, crime, drama, comedy that landed five Oscar nominations including one well deserved nomination for Leonardo DiCaprio for Best Actor. 

DiCaprio lost the Best Actor Oscar to Matthew McConaughey for his performance as an AIDS victim in “Dallas Buyers Club”. While Leo didn’t win the Oscar, it proved just how committed Leo is to his craft (especially the scene where he literally dragged himself across the floor and down stairs while on Quaaludes). It also proved that Leo has great comedic chops. 

I think the boost in confidence of his own skills came with the help of Quentin Tarantino, when Leo was casted in “Django Unchained”. Leo was able to explore a side of himself for his performance in “Wolf Of Wall Street” that even he likely didn’t know he possessed. It was a performance that we had never seen before from Leo and it’s one that I hope he soon again revisits. I love McConaughey too but sorry to say I think Leo deserved his one and only Oscar for this film.

#2: What’s Eating Gilbert Grape – 1993

Leo’s five Oscar nominations began in 1993 with his very first Oscar nominated role as the mentally challenged brother of Johnny Depp in the emotionally multi-faceted Lasse Hallström dramedy “What’s Eating Gilbert Grape?”

It just goes to show and speaks volumes that at the age of eighteen, DiCaprio was able to portray a character with a handicap that is likable, endearing, and inoffensively humorous rather than making a mockery of the disability with his performance. Being that young and giving such a complex performance like that is truly astonishing. 

Leo played Arnie Grape’s character so well that when he showed up for the film’s premiere, many people were shocked and astonished to learn that the young actor was not actually mentally disabled.

#3: Revolutionary Road – 2008

Reunited with his “Titanic” co-star Kate Winslet and directed by her husband Sam Mendes (“American Beauty”). DiCaprio took suburban domestic turmoil to new levels with his turn as Frank Wheeler. Leo gives a layered and age mature performance. 

DiCaprio is brilliant in slowly turning his love and idealism, curdling it into frustration, cruelty, and rage. It’s still among his most vicious performances.

#4: Django Unchained – 2012

Speaking of vicious performances, none is more vicious than his role as Calvin Candie in Quentin Tarantino’s masterpiece “Django Unchained”. 

When Tarantino was working on his screenplay for “Inglourious Basterds”, he intended the role of Colonel Hans Landa to be embodied by Leonardo DiCaprio, but ultimately decided that the role would be best served by Austrian actor Christoph Waltz. So, when it came time to write his western revenge flick “Django Unchained”, Tarantino knew he didn’t want to miss collaborating with Leo and wrote him a role that was utterly juicy and deliciously despicable.

Before he threw his all into the performance of horrid, slave-owning, Mississippi cotton mogul Calvin Candie, no one could have predicted that DiCaprio would be in a Tarantino flick or have risked his likability on a role that was so far from his wheelhouse. Leo eats up every opportunity he gets to be gruesome and evil and succeeds on a level he had not yet reached as an actor until “Django”. The role itself is Leo completely being braver and bolder. 

When DiCaprio’s character smashes his hand on the dinner table, the actor accidentally crushed a small stemmed glass with his palm and really began to bleed. DiCaprio ignored it, stayed in character, and continued with the scene. Tarantino was so impressed by this that he used this take in the final print. When he called cut, the room erupted in a standing ovation. DiCaprio’s hand was bandaged and he suggested the idea of smearing blood onto the face of Kerry Washington. Tarantino and Washington both liked this, so Tarantino got some fake blood together.

It took Leo some time even having to call cut in between scenes because he couldn’t handle spurting out so many racial slurs. He managed to pull it off and become his most vile and commanding role.

#5: The Departed – 2006

In his second of four collaborations with the legendary Martin Scorsese. Leo’s performance here is extraordinary but unfortunately the Academy was too blind to see that. As Leo should be on the list of all time worst snubs in Oscar history, as Leo was not given an Oscar nomination for his performance. Out of the cast only Mark Wahlberg received a nomination, while DiCaprio and Jack Nicholson was unfairly snubbed. 

DiCaprio’s performance is unquestionably way up there. His subdued performance as an everyman Irish-mafia mole who has trouble coping with his double identity is one of his great masterful performances. 

“The Departed” is elegant proof that DiCaprio knows how to reign in a performance and smoothly disappear into a character. It is an example of how you don’t need to be impressive to create something memorable and magnificent.


#1: Titanic – 1997

James Cameron’s 1997 box-office record-breaker, that still holds the record for third highest grossing film of all time, grossing over $2 Billion dollars, it was the most expensive film of it’s time. Nominated for 14 Oscars and winner of 11. “Titanic” became an all around pop cultural juggernaut and an awe-inspiring cinematic achievement. 

As a piece of filmmaking, it does for the vast darkness of the sea what David Lean’s “Lawrence of Arabia” did for the desert. It also presents a disaster movie epic with a sweeping romance, without ever losing its sense of tragedy.

Leonardo DiCaprio plays Jack Dawson in a role that Johnny Depp was originally offered, but he turned it down. Depp considers this to be a big regret. As an onscreen couple with Kate Winslet, they infuse their earnest back and forth chemistry, with so much genuine emotion that it’s hard not to get swept up in their love affair. It’s still the highpoint of everyones career, and that includes visionary and groundbreaking director James Cameron. “Titanic” is one of the greatest old-school movies to come out of Hollywood in the last 20 years.

FUN FACT: The movie’s now famous line “I’m the king of the world!”, was ad-libbed by DiCaprio. 

#2: The Departed – 2006

Scorsese finally won that elusive Oscar with his Boston crime thriller remake of the terrific Hong Kong thriller “Infernal Affairs”. DiCaprio plays a cop infiltrating the mob and Matt Damon as a mobster infiltrating the police force. It’s an intricate tale of cat-and-mouse games, but Scorsese and his screenwriter William Monahan, infuse it with so much tragedy, grittiness, twists and outstanding work from an excellent cast. 

“The Departed” is a thoroughly engrossing gangster drama with the gritty authenticity and morality we come to expect from Martin Scorsese. For 150 minutes “The Departed” delivers a visceral punch you’re unable to dodge. It’s the best American crime film since Michael Mann’s “Heat” with Al Pacino and Robert De Niro.

“The Departed” may be his most commercial film yet, as it was nominated for 5 Oscars and the winner of 4 including Best Picture, Best Director and Best Screenplay. The fluidity of the camerawork, the intricate storytelling, and the exquisite tension leave no doubt that you’re in the hands of a master filmmaker. Watching “The Departed” is taking a master class in filmmaking and ensemble acting. It’s a literal masterpiece. 

#3: The Wolf Of Wall Street – 2013

Nominated for 5 Oscars and unfairly winning none, “The Wolf of Wall Street” is another Scorsese masterpiece and one of the truly funniest films I’ve ever seen. It’s a magnificent black comedy that flies fast, funny, and at times remarkably filthy.

Terence Winter, creator and writer of “The Sopranos”, has written a marvelously comedic script to the three hour film with howlingly funny bits of dialogue. It’s evidence that Scorsese is once again at the top of his game as his art as a filmmaker continues in dazzling form.

Also it introduced us to Margot Robbie and for that we should all be forever grateful. 

#4: Django Unchained – 2012

Tarantino’s masterpiece. His magnum opus was nominated for 5 Oscars and won 2 including Best Supporting Actor (Christoph Waltz) and Best Screenplay. It’s bold, bloody, stylistically daring and Tarantino’s storytelling talents match the weight of the tale.

A supremely entertaining, richly cinematic treat. It’s an experience which manages to work in some fun (and often very humorous) genre subversions and engaging character nuance amongst the frenetic and violent gunplay that Tarantino choreographs to one of the greatest shootouts in cinema. 


#5: Inception – 2010 

Christopher Nolan’s brilliant sci-fi heist thriller has DiCaprio entering people’s dreams and stealing their thoughts, only this time for that proverbial one last job, he and his team are hired to implant an idea inside someone’s mind instead of boosting the usual cerebral data. 

“Inception” is truly an experience unlike any other and Nolan’s originality is astounding. His intriguing set pieces and astonishing visual effects are groundbreaking and completely deserving of it’s 4 Oscars for Visual Effects and Sound Mixing. 

#5: Blood Diamond – 2006

“Blood Diamond” is one powerful film. The shooting style by director Edward Zwick (“The Last Samurai”) is intense, perfectly mixing action with heart-wrenching drama. The film garnered 5 Oscar nominations including Best Picture, Best Director, Best Actor for DiCaprio and Best Supporting Actor for Djimon Hounsou. 

Exciting, compelling, the brilliant action sequences engage us viscerally. A a blockbuster with provocative ideas, brains and a political activism that make “Blood Diamond” one of most important films to come along in a long time. Even more than that, it’s a great acting showcase for Leonardo DiCaprio and Djimon Hounsou.



About Aron Medeiros

Aron Medeiros
Aron Medeiros lives on the beautiful island of Maui. He is a member of The Hawaii Film Critics Society, movie critic for Maui Watch, a commentator and cast member of the NerdWatch pod cast. He is a 2003 graduate from King Kekaulike High School. His favorite film of all time is “Back To The Future”. He has worked at Consolidated Kaahumanu Theaters for nearly 13 years as a Sales Associate and making his way up to Assistant Manager. He has loved movies since he was a young boy, learning about movies from his Grandfather and being self taught.

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