Leonardo DiCaprio, The Wolf of Wall Street

Leonardo DiCaprio’s Latest 10 Movies vs. Greatest 10 Movies

Leonardo DiCaprio

Latest vs. Greatest looks at directors, actors, actresses, screenwriters and composers to assess the state of their career as it stands.  We’ll look back at the latest 10 movies the artist has done, rate them and then average them out to see where they stand today.  We’ll also rank their 10 greatest movies and give them the same treatment to compare what they have been doing to their very best work.  (A quick side-note: if an artist is/has been a regular on a TV show we’ll also grade the seasons individually; artists need 10 projects to qualify).

Though only in his early forties, Leonardo DiCaprio has already amassed an impressive body of film work.  Overcoming the status of teen idol, he’s made increasingly wise and challenging decisions in his projects and is today one of the actors whose work I most look forward to.  Also his middle name is Wilhelm.  I had to work that in somewhere.

Kirk Cameron, Growing Pains, Leonardo DiCaprio
AHAHAHAHA, remember this? No? Well, nine-year-old DiCaprio started off on the dying gasps of Kirk Cameron’s sitcom Growing Pains. He was to Growing Pains what Oliver was to The Brady Bunch. This only has relevance to his acting career as a starting point and as a way for me to mock him as a child which I am in no way above.

Leonardo DiCaprio, Diane Keaton, Marvin's Room
DiCaprio’s film career started not long after and he quickly rose to critical prominence for starring with Robert DeNiro (who he eventually would replace as Scorcese’s go-to actor) in A Boy’s Life, Johnny Depp in What’s Eating Gilbert Grape (for which he received his first Oscar nomination) and the very underrated Marvin’s Room with Diane Keaton.

Kate Winslet, Leonardo DiCaprio, Titanic

Then he broke movies.  He, Kate Winslet, Jim Cameron and a billion teenage girls broke movies.  I was in high school when Titanic came out and I remember being at the mall (because that’s where you were supposed to be when you were a teenager) and watching as hordes of my classmates emerged from the theater sobbing so hard they could barely breathe THEN GOT BACK IN LINE TO DO IT AGAIN!

There are some people who hate Titanic just because of the total saturation it had on pop culture during the year of its dominance and because that damn song was on every radio station all day every day.  I had the happy experience of having it blasted in my house because my brother had just broken up with his first girlfriend it was “their song”.  Oh you’d thought I’d gotten over that?  MONTHS, bro, it was MONTHS!  Ahem.  Titanic.

I genuinely think Titanic is an awful movie.  Removing all of the hype and the phenomenon from it, it is a three-hour slog with a horrible script.  Cameron never writes great scripts, but the pacing and action are usually so taut you just go with it.  This movie is (brace for the pun) glacial.  I was rooting for the iceberg.  I was chanting the iceberg’s name (presumably “Iceberg”).  By the time the Titanic’s grip on America’s attention loosened, I was not a fan of DiCaprio’s.  I may have developed a facial tick connected to the sight of him.  But then he did something really, really smart.  He disappeared for about five years.

Leonardo DiCaprio, Catch Me if You Can
From 1997 when Titanic came out to 2002 when he released Gangs of New York and Catch Me If You Can, DiCaprio popped up only in 2000 for the forgettable The Beach. He stayed off the radar. I think it was that savvy move, coupled with reappearing partnered with Scorcese and Spielberg films, that allowed him to be taken seriously as an actor by people who pigeonholed him as a teen idol (like me).  He has from then on made very calculated, very directed choices in his projects that have developed him as an actor to the point where today he’s not instantly associated with the “King of the World” moment.

Gangs was an important film for DiCaprio because it marked the beginning of his ongoing partnership with Martin Scorcese.  DiCaprio has now appeared in five Scorcese films, the latest of which (The Wolf of Wall Street) today earned him his fourth Oscar nomination.

Catch Me If You Can is a wonderful film that gets overlooked in the canons of the principals (Hanks, DiCaprio, Spielberg), but it’s a fantastic movie.  The film got stolen a bit by Christopher Walken, who plays DiCaprio’s father, but the story of the con man Frank Abagnale is, if anything, underplayed in Spielberg’s film.  The real story of his varied impersonations of various professions should be read by any fan of a good non-fiction yarn.

Leonardo DiCaprio, Jennifer Connelly, Blood Diamond
In the following years, DiCaprio would do two more Scorcese films, The Aviator and The Departed, the latter winning Best Picture.  I think The Aviator is a great performance, but not necessarily a great movie.  I have tried really hard to like The Departed (even watched it again for this article) and I can’t.  To me, it’s the same issue I have with most of Scorcese’s work: it’s a lot of profane rambling without any compelling narrative.  Obviously that’s a minority opinion and for whatever reason I thought The Wolf of Wall Street, which is more profane than The Departed, worked.

The real gem of that period of DiCaprio’s to me is Edward Zwick’s Blood Diamond.  I don’t think there is any harder accent to pull off than South African (possibly Kiwi).  DiCaprio puts in one of his best performances as a mercenary helping Djimon Honsou search for his son.  It’s a powerful, powerful film.Inception, Cobb, Leonardo DiCaprio
We have not, since this column began, had the chance to highlight anyone who was in Chris Nolan’s Inception.  DiCaprio, who leads one of the best ensembles one could ever ask for, is outstanding in what I truly believe is the best film released in the last decade (It’s this or The Dark Knight for me).  I could write two thousand words on Inception alone, the brilliance of its nuance, complexity and the ambiguity of its end, but suffice to say that anchoring that film gave DiCaprio a special place in my movie memories vault for life.Leonardio DiCaprio, Django Unchained

One thing DiCaprio has not gotten a chance to do was play the villain, but Tarantino gave him a loathsome plantation owner in Django Unchained for which he probably should have won his first Oscar (DiCaprio now with four noms is getting to the point where he’s going to be considered “due” soon and win for something undeserving as is Academy protocol).  The entire dinner scene is one of the ugliest, white-knuckled, tense moments I’ve ever seen.  It rivals the opening of Tarantino’s Inglorious Basterds.

So let’s tally up the last ten DiCaprio films:
1. The Wolf of Wall Street (2013)…….8.75
2. The Great Gatsby (2013)……………….4.75
3. Django Unchained (2012)……………….8.75
4. J. Edgar (2011) …………………………………..5.75
5. Inception (2010) ………………………………10.00
6. Shutter Island (2010)………………………..9.50
7. Body of Lies (2008) ………………………….. 5.00
8. Revolutionary Road (2008) …………… 3.50
9. Blood Diamond (2006)………………………9.50
10. The Departed (2006) …………………….. 5.50

Leonardo DiCaprio

Owing mostly to my tastes on The Departed and Revolutionary Road (Mendes and American ennui are not a good combo for me), both of which others might rate much higher, DiCaprio’s current average is only 7.1 (which still is not by any means bad).

1. Inception (2010)…………………………………10.00
2. Blood Diamond (2006) ……………………..  9.50
3. Catch Me If You Can (2002)……………   9.50
4. Shutter Island (2006) ………………………..  9.50
5. Django Unchained (2012) …………………  8.75
6. The Wolf of Wall Street (2013)………,,..  8.75
7. Marvin’s Room (1996)…………………………  7.75
8. What’s Eating Gilbert Grape (1993)..,,,.7.75
9. Gangs of New York (2004) …………………..6.25
10. The Aviator (2002) ………………………………6.00

Solid greatest average on par with Will Smith’s.  DiCaprio still has thirty to forty years of films left in him so this is a very early evaluation of his body of work and already he’s made his mark.  I see growth in his acting with every project he takes on and I truly believe his best performances are in his future.Leonardo DiCaprio, The Wolf of Wall Street, Oliver Stone

14 thoughts on “Leonardo DiCaprio’s Latest 10 Movies vs. Greatest 10 Movies”

  1. Yeah. Great post… I’m a huge fan of DiCaprio. And I won’t be agreeing with your rating of The Departed. But each to his own… The rest I am satisfied with. Blood Diamond, Inception, Catch Me If You Can and Shutter Island deserve all the praise they get.


    1. Thanks for the comment! Well it won Best Picture, so obviously mine is not a mainstream view and DiCaprio was certainly good in it. He in no way has anything to do with my criticism of that film. I’m impressed with any actor who I see learning and growing and who picks their projects with a strategy toward bettering their career and DiCaprio has done that extremely well his whole career.


      1. Indeed he has. Its always worth watching his films as compared to some other actors who pick some right silly movies to do sometimes, just for the paycheck. I can proudly say that DiCaprio is my favourite actor.


      2. He’s on a very short list of someone whose participation in a project immediately commands my attention. He’s not attached officially to another film at this point, which is unique because most actors have two or three in the pipe. Given his relationship with Scorcese, he’s probably just waiting to see what they’ll do together next. It’s a partnership that has certainly worked out well so far.


  2. He’s great a real talented guy, an earlier pick of his I always enjoy is The Beach but you can’t beat him in the likes of Inception and an all time favourite like Catch Me If You Can! Great Post 🙂


    1. Thanks, man! Maybe I need to rewatch The Beach. I end up watching so many films for each of these pieces that some get lost in the cracks. Catch Me If You Can just makes me smile. Fantastic movie.


      1. But if it turned even one jaded teenager onto Shakespeare, it was justified. I’m a big proponent of radical and startling approaches to the Bard; anything to bring contemporary audiences into the fold. In Shakespeare’s day, they didn’t have elaborate period costumes and sets; in general, the actors dressed like Elizabethans, regardless of the era of the story. I see no difference between that and putting Shakespearean actors in modern dress today.
        Gangs of New York was revelatory. Yes, Bill the Butcher was the flashy role in that movie, but DiCaprio went up ten notches in my estimation after I saw it (and I saw it three times in the theater). It was only after that that I saw Gilbert Grape for the first time. And then I felt bad for misjudging poor Leo. The man is a consummate actor.


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s