There are few actors with the level of name recognition as Leonardo DiCaprio – in fact, “Leo” usually suffices. But this kind of global renown wasn’t always a reality for young Leo and like most talented actors, he got his humble start starring in commercials – but this didn’t last long. After moving on from a slew of TV ads and he got his start on the silver screen starring as Josh in the movie Critters 3.
Leonardo DiCaprio Movies – History & Background
He then followed this masterpiece up with a stirring supporting performance in the emotionally harrowing What’s Eating Gilbert Grape before moving on to star in the gritty coming of age film The Basketball Diaries. It was here that Leonardo DiCaprio shot to international stardom, and with gusto.
For a long time, Leo was a heartthrob; his face was plastered over teenage walls and magazine covers like no tomorrow. He was essential the coveted ‘it’ boy of the mid to late ’90s. His killer combo of boyish good looks and highly-developed acting chops (especially considering his young age) saw Leo go on to work with acclaimed Directors Baz Luhrman (Romeo + Juliet) and James Cameron (Titanic) in the next years after his first starring role in a feature film.
By the year 2000, Leo was an untouchable tour de force of young-adult angst, with many lauded performances under his belt.
However, it was clear that young Leo was beginning to be typecast – so he moved to shift his image. After taking a couple of years off, he returned with a romper of a year in 2006, starring in Blood Diamond and Scorsese’s masterpiece The Departed; proving that he could be so much more than just a heartfelt pretty-boy.
In the years that followed, DiCaprio became a Hollywood stalwart, working with the likes of Tarantino, Alejandro González and Christopher Nolan – not to mention his continued and excellent work with Scorsese. However, amidst this impressive back-catalogue, there are DiCaprio movies that are more impressive than the others. And with the upcoming, and the much-anticipated Once Upon A Time in Hollywood, we here at Man of Many decided it was time to make a call once and for all, which are best – for greater context we’ve set our list up against powerful aggregators Rotten Tomatoes & IMDB.
So here it is, old sports, a list of the top 10 Leonardo DiCaprio movies ranked.
10. The Basketball Diaries
The film that broke Leonardo DiCaprio’s movie career, Scott Kalverts The Basketball Diaries is a coming of age tale wrapped in teen angst and genuine heartache. Whilst the critical reviews are mixed, Leo’s performance was undeniably raw and intense, as was the film’s subject matter which explored themes of sex, drugs, social and familial expectations, in a very realistic fashion.
While you might not finish this movie thinking “Bloody hell that was a great flick”, it’s undeniable that the beginnings of a very successful acting career were in the making when Leo took on the role of Jim Carroll.
Rotten Tomatoes: 46%
9. Shutter Island
Leo’s other standout film from 2010, Shutter Island (Directed by Martin Scorsese) is a film built on its crazy twist – which we’ll leave unspoiled today for those who haven’t seen it. What we will say, is that it takes a great poker face to pull of a mystery with so many moving parts, without giving it away or coming across as obvious – luckily, DiCaprio was just the man for the job.
It’s safe to say that Shutter Island is a classic in the noir mystery space, solidified by Leo’s ability to shapeshift into anybody he chooses (and pull off an authentic old-timey detective accent).
Rotten Tomatoes: 68%
8. Romeo + Juliet
Filmed during the absolute peak DiCaprio studmuffin era, Romeo + Juliet was a modern reimagining of Shakespeare’s iconic ‘Romeo & Juliet’ (they changed the ampersand to a ‘+’ symbol you see, #modern). Whilst the movie is frantically paced, as per Lurhman’s core style, Leo brings a smoothness to the role of Romeo – and although he is an emotional basket case for 99 per cent of the film, there is no denying that his performance as Romeo is still held dear by millennials all over the world. As a cult hit, this is one of our most entertaining Leonardo DiCaprio movies.
Rotten Tomatoes: 72%
7. Django Unchained
In one of DiCaprio’s few supporting roles, there was movie magic to be had. Working with rockstar director Quentin Tarrantino for the first time, Leo found his sinister side as ‘Monsieur Candie’ in Django Unchained, without losing sight of the humour and ridiculousness of his character.
Switching effortlessly from condemning a man to be torn apart by hunting dogs, to swapping straight-Fyre banter with Samuel L. Jackson in old-man costume, Leo’s performance as Candie in Django Unchained proved he could play well with others (despite somewhat stealing quite a few scenes).
Rotten Tomatoes: 86%
6. What’s Eating Gilbert Grape
Starring Johnny Depp and a very young Mr. DiCaprio, What’s Eating Gilbert Grape is a film not for the faint of heart. This film made the list because playing a character with a mental disability is on its own, a huge challenge. It’s an even more daunting task to do it when you’re a relative unknown and one that’s extremely young.
Luckily, Leo’s depiction of Arnie was spot-on, earning the film and him as a performer rave reviews from both critics and movie-goers alike.
Rotten Tomatoes: 90%
Directed by Christopher Nolan – the maestro of the art of mind-fuckery – Inception signified Leo’s strong entrance into the smart-thriller category. Having done heartthrob, heady drama and intelligent action films to a T, DiCaprio dipped his toe into this new genre for him and boy did it pay off.
Bringing a real sense of drama to the mourning of his character’s late wife, along with a real feeling of longing to be with his estranged children, Inception just wouldn’t have been the same without Leo – even with its already impressive cast, script and seasoned director.
Rotten Tomatoes: 87%
As the film that helped make DiCaprio’s career, we perhaps wouldn’t have many of the films starring Leo we hold dear today were it not for the sappy yet genre-defining Titanic. It’s incredible to think that at the time of filming Titanic in 1996, Leonardo DiCaprio was just 22 years old, and Kate Winslet was only 21 years old. Once the highest-grossing film of all time (and for a bloody long time at that), you’d be hard-pressed to find someone born before 2005 who hasn’t seen James Cameron’s Titanic – and you better believe that Leo’s star power and perfect casting played a major part in putting bums in seats.
Rotten Tomatoes: 89%
3. The Wolf of Wall Street
In what is his most debaucherous film to date, The Wolf of Wall Street turned heads upon release, if nothing else. With the film being a box office success as much as it was a critical one, Leo’s performance as the notorious Jordan Belfort and IRL Wolf of Wall Street was all stations go, the whole time.
From doing blow out of a hookers buttcrack in the opening scene to attempting to wriggle down a short set of stairs after a shitload of ‘ludes, DiCaprio’s commitment to the role was admirable – and he was funnier than anything we’d since him in before.
Rotten Tomatoes: 79%
2. The Revenant
It due to his performance as Hugh Glass – an American frontiersman back in 1823 – that Leo finally grasped his fingers around that coveted, and wildly overdue, Academy Award. In pushing himself to breaking point day-in and day-out to ensure his performance was authentic, and for completely disappearing within the role, DiCaprio took the film to a level that no other actor could.
It was working with the visionary Alejandro González (director of Birdman or: The Unexpected Virtue Of Ignorance) in The Revenant that Leo was able to finally make the world forget who he was and that he was striving for an award, and solidify himself as a world-class actor worthy of our continued attention.
Rotten Tomatoes: 78%
1. The Departed
Working with one of the best directors of all time, Martin Scorsese, Leo was on a mission to toughen up his image in the Oscar-winning film The Departed – and undoubtedly, to put his acting skills to the test. Starring alongside heavyweights Alec Baldwin, Mark Whalberg and Jack Nicholson, DiCaprio’s best performance came as a result of the perfect movie mix: great script, great director and experienced co-talent.
Be it holding a gun to a man’s head or bashing an Irish crony to bits in a general store, DiCaprio brought a level of complexity to a repressed Irish-Catholic cop that felt truly authentic. His interpretation of the character played beautifully within the set story and thus, The Departed takes the title of Leonardo DiCaprio’s best film.
Rotten Tomatoes: 91%
What is the best Leonardo DiCaprio movie?
Some of the best Leonardo DiCaprio movies are The Revenant, Once Upon a Time in Hollywood, The Wolf of Wall Street, The Departed, Inception, and Titanic, to name a few.
How old was Leonardo DiCaprio when he did Titanic?
Already a seasoned actor, Leonardo DiCaprio was just 21 years old when he starred in Titanic.
How many movies has Leonardo DiCaprio died in?
As of 2020, Leonard DiCaprio has died in 9 films.