Ranking 15 films starring Leonardo DiCaprio in order of greatness
“I just want to keep doing what I’m doing and hopefully people will watch my movies.” – Leonardo DiCaprio
Enigmatic and charming, Leonardo DiCaprio’s presence on-screen is iconic and sublime. A stellar performer, DiCaprio was born in Los Angeles, California, on November 11, 1974. Having begun his career in sit-coms in the late 1980s, it was not until 1993 that Leo starred in a major film. Following his role in 1993 effort This Boy’s Life, he received acclaim and an Oscar nomination for his supporting role as a mentally impaired boy in What’s Eating Gilbert Grape in the very same year. In 1997, Titanic catapulted Leo to superstardom and he has not looked back ever since. Following a few unsuccessful commercial stints, in 2002, he finally landed two successful features in Catch Me If You Can and Gangs of New York; the latter marking the beginning of his association with Martin Scorsese. Leo later went on to become Scorsese’s blue-eyed boy (literally) and starred in many successful features.
DiCaprio has enjoyed a wonderful career in which he has collaborated with legendary directors like Quentin Tarantino, Alejandro Gonzalez Iñárritu, Christopher Nolan, Steven Spielberg and many more, delivering incredible performances with every passing movie, he cannot be typecast into a particular genre. His roles are scattered all over the spectrum; starting from a scallywag to a notorious gangster, from a vicious plantation owner to a lovesick billionaire, from a fraudster stockbroker to a dream-thief—Leo has done it all (although, we would say that he definitely has a knack for playing fraudulent billionaire). He is not a classic American method-actor; he does not use anecdotes from a character’s personal life. He has certain ground-breaking ideas and mysterious tricks up his sleeve which often leaves the director spellbound.
DiCaprio has ruled the hearts of the audience for decades with his boyish charm and exquisite mastery over his craft. However, as compensation, the actor has had to give up his ‘award-winning luck’. That said, 2016 proved to be a curse-breaker for him as he finally won the Academy Award for his brilliance and resilience in the film The Revenant, after being nominated for the sixth time. Cheered on by the audience, Leo’s win was definitely the most desirable.
Fans are waiting eagerly for Leonardo DiCaprio’s next film, Killers of theFlower Moon at Paramount, which is yet another Scorsese-DiCaprio combo. The film is supposedly about the FBI investigations regarding the Oklahoma murders in the 1920s which allegedly had underlying ties to oil deposits.
On his 46th birthday, let us toast to this legend’s health and career, (quench our Leo-mania) and take a look at his 15 best films of all time.
Leonardo DiCaprio’s 15 best movies:
15. Revolutionary Road (Sam Mendes, 2008)
April and Frank Wheeler’s relationship is seemingly perfect on the outside. Their relationship is strained by their different expectations and purpose in life, and as they hope to salvage their marriage and escape the drudgery, tragedy strikes.
11 years after their on-screen magic in Titanic, the iconic duo Kate Winslet and Leonardo DiCaprio return as a dysfunctional couple trying to save whatever love they have left for each other. Emotionally moving, their powerful and nuanced performances cease them from being mere actors; they seem too familiar to the audience. Committed to their roles, Winslet is gorgeous and pitiful as a woman having failed her ‘American Dream’, while Leo’s varying emotions from being a violent husband to a defeated man makes the movie raw and captivating.
“I’m not happy about it, but I have the backbone not to run away from my responsibilities.”
14. The Great Gatsby (Baz Luhrmann, 2013)
An ambitious and faithful adaptation of F. Scott Fitzgerald’s novel of the same name, The Great Gatsby is the story of the mysterious and affluent Jay Gatsby whose lavish, waywardly parties at the height of the roaring twenties attract the curious interest of his neighbour and war veteran, Nick Carraway.
According to Fitzgerald’s daughter, “Scott would have been proud” of the film. Despite the visual splendour, theatrical flamboyance and performative extravagance, it was criticised as “a spectacle in search of a soul”. DiCaprio as the sensitive lonely millionaire outdoes himself yet again with each and every role — as Gatsby, he is repulsive yet charming. Though Luhrmann’s film was vehemently criticised, it made a whopping $300 million at the box office winning accolades from the audience.
“I knew it was a great mistake for a man like me to fall in love.”
13. Once Upon A Time in Hollywood (Quentin Tarantino, 2019)
In a rapidly changing film industry, Rick Dalton, an actor of the yesteryear, gradually losing his fame, and his stunt double, Cliff Booth, face the trials and tribulations of trying to stay relevant as well as the threat of the Tate-LaBiance murder. “Multiple storylines in a modern fairy tale tribute to the final moments of Hollywood’s golden age”.
Nominated for 12 Academy Awards, this film gifted Brad Pitt his very first Oscar for ‘Best Actor in Supporting Role’. Tarantino’s tribute to his beloved ‘60s LA is thoroughly enjoyable. Leonardo DiCaprio as Rick Dalton is phenomenal and he definitely is the showstopper in the film. Pitt as Cliff Booth is infectious and they share an iconic camaraderie on-screen. Margot Robbie as Sharon Tate delivers an incredible performance as well. The nearly three-hour-film has the right balance of violence and fun amidst a sensitive and authentic portrayal of the best era of cinema. The way Tarantino weaves in nostalgia while invoking the history of Hollywood, along with a brilliant ensemble, makes the film tantalizing; almost a reminder that Tarantino is competing with his own legacy.
“When you come to the end of the line with a buddy who is more than a brother, and less than a wife, getting blind drunk together is the only way to say farewell.”
12. Gangs of New York (Martin Scorsese, 2002
Due to rising tension among the Protestant and Catholic communities in Five Points, Priest Vallon is mercilessly slaughtered by William “Bill the Butcher” in 1846. Vallon’s son who witnesses the killing, returns to the town in 1862, using the alias of Amsterdam to murder Bill and avenge his father’s murder.
Nominated for ten Oscars, Gangs of New York was the first Martin Scorsese film Leo starred in, and the rest is history. While critics have praised Daniel Day-Lewis’ “electrifying performance” as the ruthless Bill, DiCaprio’s Amsterdam is a quintessential Dickensian hero whose eyes serve as the narrative lens. He does a spectacular job paving his way into Scorsese’s heart which marked the beginning of a new era.
“When you kill a king, you don’t stab him in the dark. You kill him where the entire court can watch.”
11. The Aviator (Martin Scorsese, 2004)
Howard Hughes, an aviator, is also an eccentric director famous in the film industry. However, his growing OCD and paranoia become a threat to his legendary reputation and career; personal demons and past reminiscence make it increasingly difficult for him to take control of his life.
A second successive Scorsese film, Leo earned his second Academy Award nomination with his brilliant and insightful portrayal of Hughes, to the point where the eccentric tycoon becomes an object of sympathy and admiration. He thrives in Scorsese’s artistic and scintillating approach. His acting prowess, well-gauged by the visionary director, was put to good use. Years later, Leo was quoted saying “I felt I could truly own the term artist by working alongside him”.
“Sometimes I truly fear that I… am losing my mind. And if I did it…. It would be like flying blind.”
In a sleepy town in the Midwest, Gilbert Grape takes care of his morbidly obese mother, Bonnie, and his mentally-challenged eighteen-year-old brother, Arnie. He is also in love with a married woman named Becky and is caught up in this vicious cycle of responsibilities.
At 19, Leo received his first-ever Oscar nomination for his supporting role as Arnie Grape, a mentally impaired boy. His performance is vivid and moving, often difficult to watch; when Arnie goes to wake his dead mother, he first thinks she is asleep. However, as soon as he realises what has passed, the distraught expression on his helpless face is surely going to move the audience to tears. Depp as Gilbert is outstanding, but Leo’s performance is “of astonishing innocence and spontaneity” which brings in “a touching credibility to a very difficult part”.
“Mama, Mama!… Wake up! …. You’re hiding, huh? …. I know that. …. Wake up! …. Mama, wake up! …. Mama, stop it now! …. Stop, Mama! …. Stop it.”
9. Catch Me If You Can (Steven Spielberg, 2002)
Frank Abagnale is a notorious check fraudster who manages to dupe people of millions with masterful trickery and deceit. He is pursued by FBI agent Carl Hanratty who is determined to catch the con artist.
Suspenseful and fun, Spielberg’s twenty-year dream project had the dream combination of Tom Hanks and Leonardo DiCaprio. The dynamic duo delivered enthralling performances which add thrill to this well-crafted cat and mouse chase. Cheeky and charming, Leo is effortlessly convincing as the famous fraudster.
“An honest man has nothing to fear, so I’m trying my best not to be afraid.”
8. Blood Diamond (Edward Zwick, 2006)
Solomon Vandy, who is abducted and coerced into working in mines, discovers a priceless diamond. He finds an unlikely ally in the smuggler, Dany Archer, who promises to help Solomon find his family, his prize being the diamond. The film unravels as they embark on this quest through dangerous territories motivated by their personal interests.
Djimon Hounsou as Solomon does justice to his character which gets him an Oscar nomination; so, does Leo, who is nominated for the third time due to his epic portrayal of the frivolous Danny Archer. He even goes to the extent of mastering the South African accent for this role. Intense, vulnerable and emotional, the actors establish a lovely understanding on-screen which makes it a memorable watch.
“Sometimes I wonder… will God ever forgive us for what we’ve done to each other? Then I look around and I realize… God left this place a long time ago.”
7. The Revenant (Alejandro Gonzalez Iñárritu, 2015)
True to the meaning of the word which refers to someone returning from the jaws of death, The Revenant is based on a man’s terrifying quest for survival when pitted against Nature’s wrath and the terrible betrayal of his compatriots.
Leo, who had been snubbed by the Academy multiple times, rightfully took the much-coveted Academy Award for his role as Hugh Glass. Like Hugh, he showed unwavering courage and determination while preparing for the film; despite being a vegetarian, he went to the extent of consuming an actual raw liver to add realism to the film. Outstanding performances by the rest of the cast is overshadowed by Leo’s gut-wrenching portrayal of a helpless man surviving by virtue of his will to live. “I can name 30 or 40 sequences that were some of the most difficult things I’ve ever had to do”, he was quoted saying, “whether it’s going in and out of frozen rivers, or sleeping in animal carcasses, or what I ate on set. I was enduring freezing cold and possible hypothermia constantly.”
“As long as you can still grab a breath, you fight. You breathe. Keep breathing.”
6. The Wolf of Wall Street (Martin Scorsese, 2014)
Based on the true story of a stockbroker named Jordan Belfort, Scorsese’s hedonistic saga of sex, drugs and crime chronicles the former’s journey from rags to riches by defrauding wealthy investors in billions, which ultimately has an adverse effect on his life.
One of his most iconic roles, DiCaprio rightfully earned an Academy Award nomination for his stellar performance as the roguish Belfort. As Leo himself said, it is “a cautionary tale… like a modern-day Caligula- The Fall of Roman Empire”. He spent “many months” with the real-life Jordan Belfort and even videotaped the latter’s expression to impersonate him better when high on extra-strong Lemon Quaaludes. Leo has further added, “It’s the biggest adrenaline dump… I haven’t been able to step on a set since”.
“On a daily basis I consume enough drugs to sedate Manhattan, Long Island, and Queens for a month. I take Quaaludes 10-15 times a day for my ‘back pain’, Adderall to stay focused, Xanax to take the edge off, pot to mellow me out, cocaine to wake me back up again, and morphine… Well, because it’s awesome.”
5. Shutter Island (Martin Scorsese, 2010)
US Marshal Teddy Daniels and his newly assigned partner, Chuck Aule, travel to the Ashcliffe Hospital on a remote island to investigate the disappearance of the patient. As Teddy delves deeper into the investigation, he realises the sinister nature of the asylum and its inmates; he must confront the ghosts of his past as well as his fears to be able to successfully leave the island.
Intense and unsettling, Shutter Island is one of Scorsese’s most phenomenal yet underrated works. Provocative, the film challenges the sanity of the viewers. He pervasive gloom and anxiety is heightened by Leo’s outstanding performance as Teddy Daniels, a man haunted by his traumatic past. Mark Ruffalo adds a brilliant dimension to the former. Scorsese pulls off the greatest plot twist at the end of the movie, leaving an indelible mark on the minds of the viewers.
“Which would be worse – to live as a monster? Or to die as a good man?”
4. Titanic (James Cameron, 1997)
Rose, now very old, a survivor of the Titanic, reflects on the tragic and fateful journey she undertook on board the world-famous Titanic. An aristocrat, she meets and falls in love with Jack Dawson, a handsome and penniless artist. As tragedy strikes in the form of a giant iceberg, the star-crossed lovers fight for survival while the majestic Titanic sinks into the heart of the Atlantic.
Titanic earned 11 Oscar nominations, yet, quite astonishingly, Leonardo DiCaprio did not get a single one of them. Although his co-star Kate Winslet earned one, Leo was deprived of an Academy Award honour. DiCaprio who had always been used to playing complex and layered characters feared that his role in this movie was far “too easy”. Matthew McConaughey would have almost be cast as Dawson which later went on to become one of Leo’s most prominent role and catapulted this dashing star to superstardom. Leo’s innocence and liveliness as young jack Dawson remain etched in the hearts of millions of Rose-s all around the world.
“Promise me you’ll survive. That you won’t give up, no matter what happens, no matter how hopeless. Promise me now, Rose, and never let go of that promise.”
3. Django Unchained (Quentin Tarantino, 2012)
Rescued by a German travelling bounty hunter, Dr. King Schultz, Black slave and “the fastest gun in the South”, Django Freeman, sets out on a journey to free his wife, Broomhilda, from a despicable, narcissistic and malicious Mississippi plantation owner and brutal slave-fight enthusiast, Calvin Candie.
DiCaprio is downright vile and abominable as Candie. He found it exceedingly difficult to play the character that was so loathsome and evil. “For me”, he said, “the initial thing obviously was playing someone so disreputable and horrible whose ideas I obviously couldn’t connect with on any level.”
He went on: “I remember our first read-through, and some of my questions were about the amount of violence, the amount of racism, the explicit use of certain language… My initial response was, ‘Do we need to go this far?” Tarantino confirms by saying, “He’s the first villain I’ve ever written that I didn’t like. I hated Candie, and I normally like my villains no matter how bad they are.” Leo even ended up cutting his hand while the cameras were rolling, but that did not deter him from not going through with the scene. Despite his immense dedication, he did not get nominated by the Academy. However, needless to say, Calvin Candie is one of the finest performances of his career.
“Now bright boy, I will admit you are pretty clever. But if I took this hammer here and I bashed it in your skull, you would have the same three dimples in the same place as old Ben.”
2. The Departed (Martin Scorsese, 2006)
While constantly infiltrating each other’s’ organisation, Boston Police officer, Billy Costigan, and Boston Mob member, Colin Sullivan, are embroiled in a vicious cat and mouse chase. They find moles in their respective organisations and go to various lengths to prevent that from getting exposed.
One of Scorsese’s best films to date, The Departed boasts of a heavyweight ensemble which includes Jack Nicholson, Matt Damon, Mark Wahlberg and Leonardo DiCaprio among others. According to Entertainment Weekly, “If they’re lucky, directors make one classic film in their career. Martin Scorsese has one per decade (Taxi Driver in the ’70s, Raging Bull in the ’80s, Goodfellas in the ’90s). His 2006 Irish Mafia masterpiece kept the streak alive.” In his third successive film with Scorsese, Leo as the hot-headed Costigan brings a wonderful emotional depth and maturity to his character. Fiercely entertaining, it is a shame how Leo did not get a nomination at the Academy.
“When I was your age, they would say you could become cops or criminals; today what I’m saying to you is this: When facing a loaded gun, what’s the difference?”
1. Inception (Christopher Nolan, 2010)
Dom Cobb, a professional ‘extractor’, engages in stealing information by infiltrating into the unknowing subconscious of his targets. He is posed with an excellent offer where his criminal history shall be erased in lieu of a mammoth task; he has to implant an idea into the subject’s mind instead of extracting it.
Inception has been termed as one of the best 21st-century films, and Empire magazine had high praise for the movie when they said, “it feels like Stanley Kubrick adapting the work of the great sci-fi author William Gibson.” Nolan’s mind-bending movie that transcends the textbook definition of dream-reality brought home four academy awards; Leo’s superb portrayal of the slick and masterful Cobb will go down as one of his most memorable characters in the history of his career.
“Well, dreams, they feel real while we’re in them, right? It’s only when we wake up then we realize that something was actually strange.”