Hands down, Leonardo DiCaprio is one of the most versatile actors in Hollywood today.
And over the course of his career has had the opportunity to play characters from all
over the map.
Since becoming a household name in the mid nineties, the actor’s work has only gotten
better.
So it feels like now is the right time to take a look at The Amazing Evolution of Leonardo
DiCaprio in Famous Hollywood Movies.
After playing a series of minor parts on the small screen, DiCaprio really got the audience’s
attention for the first time with his performance in 1993’s Whats Eating Gilbert Grape.
The actor took on the role of Arnie, and played the younger brother to Johnny Depp’s titular
character.
Viewers were blown away by DiCaprio’s convincing portrayal, and at the age of 19, was nominated
for an Oscar because of it.
In the big scheme of things, the movie isn’t the highest grossing of his career, but it
might be the most important.
After the entertainment bigwigs started to take notice of the talented young actor, Leo
did what 99% of actors do: Shakespeare.
And what great actor doesn’t have a little Shakespeare in their background?
In 1996, he was cast as the lead in Baz Luhrmann’s modern take on Romeo + Juliet.
Working opposite Claire Danes, the film is a total audiovisual trip.
The main obstacle people run into when reading William Shakespeare’s works is the language
structure.
And while the original dialogue remains intact, the contemporary setting bridged the gap.
Making this one of the most accessible versions of the story, even if the contrast seems jarring.
As a result of it’s approachability, the movie was a big hit with audiences.
And suddenly people became a lot more interested in what DiCaprio would do next.
It’s a good thing viewers liked him, because in the following year, his stardom would be
inescapable.
To say that Titanic kicked ass at the box office would be a gross understatement.
The 1997 cinematic juggernaut smashed records that hadn’t even been set yet, and to this
day remains the most successful film on DiCaprio’s resume.
And is second only to Avatar when talking about the highest worldwide grosses of all
time.
There isn’t a fan out there who doesn’t have the lyrics to Celine Dion’s “My Heart
Will Go On” memorized.
As Jack, Leo is a third-class passenger who falls for a first-class lady named Rose.
DiCaprio and co-star Kate Winslet are so perfect together, that even the happy moments their
characters share are heartbreaking.
Director James Cameron brought stunningly realistic visuals to the screen like the public
had never experienced before.
Playing Jack put Leonardo DiCaprio on a trajectory that ultimately made him the star he is today.
Like we’ve said before, if you want something done right, just hire Tom Hanks.
The man can do no wrong.
And DiCaprio was along for the ride as Frank Abagnale Jr. in 2002’s Catch Me If You Can.
Based on the story of a real-life conman, the movie follows Leo’s character as his
deceptions become increasingly sophisticated.
With Hanks alongside as the man obsessed with taking him down, their cat and mouse dynamic
is so engaging that you can’t help but root for them both.
But just days earlier, audiences were watching the actor in a different movie.
Once in a blue moon, a powerful actor attracts a powerful director, and together they perform
motion picture witchcraft.
In 2002, Martin Scorsese tagged DiCaprio to play the protagonist in his movie Gangs of
New York.
Released five days before Catch Me If You Can, 2002 was shaping up to be a pretty good
year for Leo.
The famous director is known for having very specific criteria during the casting process
for his films, so being hand-picked by him is kind of a big deal.
Since the Scorsese train stops for nobody, the actor hopped aboard at his first opportunity.
And as we’ll see, this collaboration marks the beginning of a beautiful big-screen friendship.
When Scorsese needed someone to play the eccentric Howard Hughes in 2004, he knocked on Leo’s
door.
Clocking in at nearly three hours, The Aviator won five of the eleven Oscars it was nominated
for.
And DiCaprio even took home a Golden Globe for Best Actor.
The critics who were able to hold their bladders long enough to make it to the end praised
the complexity of his performance.
And those who used the movie’s runtime as an excuse not to see it must be forgetting
that Titanic was almost a half hour longer, and we didn’t hear any complaining back
then.
It seems, the dynamic duo of Scorsese and DiCaprio can’t lose.
And quite frankly, their friendship is good for everyone.
Some fans argue that the actor does his best work under Scorsese, and the two have created
some phenomenal movies together.
But the one that finally bagged Scorsese an Oscar was 2006’s The Departed.
Stacked with talent from top to bottom, the film saw DiCaprio holding his own beside major-league
talents Jack Nicholson, Matt Damon, and the delightfully foul-mouthed Mark Wahlberg.
Anyone who still thought Leonardo DiCaprio was doomed to a life of pretty boy romance
acting was proven so wrong by this movie.
As an undercover cop, his assignment is to gain access to an Irish gang.
In case you haven’t seen it, we don’t want to spoil the plot.
But seriously, you should probably get on that.
2010 was another banner year for the actor.
He reunited with Scorsese for the thriller Shutter Island.
And again audiences were captivated.
But DiCaprio also made a new friend that year.
A man who happens to be responsible for some of the most enthralling movies ever made;
Christopher Nolan.
A writer, producer, and director, Nolan is a Tinseltown triple threat.
And while there’s a fiery debate between fans about which movie is his best, Inception
has to be the coolest.
It’s a complete ocular spectacle, and DiCaprio carries the audience effortlessly through
the labyrinthine dream levels.
He gives his character Cobb a depth, and is probably the only actor who can completely
lose his shit and handle his shit, all at the same time.
Speaking of losing his shit, the actor got the opportunity to do so as the depraved Calvin
Candie in 2012’s Django Unchained.
The Quentin Tarantino flick follows two men as they try to recover one of Candie’s slaves.
His performance is genuinely unsettling.
And he got so into it that while filming an intense scene, the actor smashed a real glass,
and sliced his hand wide open.
But, ever the professional, DiCaprio doesn’t miss a beat.
It’s an intense moment, and it’s made even crazier by the rabid, strung out look
on his face.
In 2013, the actor reunited with Scorsese and the world was introduced to a little movie
called The Wolf of Wall Street.
The story of excess not only jumpstarted Margot Robbie’s career, but certain governments
think the movie is so offensive, that it’s even been banned in multiple countries.
Nevertheless, it tells the story of Jordan Belfort, a crooked stockbroker with unorthodox
taste.
Sex, drugs, parties, The Wolf of Wall Street has it all.
And when he lost out to Matthew McConaughey in the best actor category at that year’s
Oscars, fans were pissed.
Thankfully they didn’t have to stay that way for long.
Because in 2015, after appearing in nearly thirty movies, the actor finally went home
with a trophy from the Academy for his work on The Revenant.
It was well earned, too.
The filming conditions were horrible, and DiCaprio underwent a complete physical transformation.
He’s hardly recognizable as Hugh Glass, a man who gets attacked by a bear then left
for dead by his group.
A lot of people think he won an Oscar for the wrong movie, but we’ll leave that up
to you.
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Did we miss any of your favorite Leonardo DiCaprio moments?
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