Scorsese Watch: The Wolf of Wall Street (2013)

Watched:  09/02/2026

Format:  Started on Hulu on August 30th, they dropped it and Apple+ picked it up

Viewing:  Second

Director;  Scorsese

I saw The Wolf of Wall Street (2013) once before in the theater, and wanted to watch it again, but it's three hours.  And I figured Jamie would want to see it eventually, and at three hours, I was limiting how often I'd invest in watching the flick.  

Plus, when I remember particularly liking a movie, I am not a person who watches it over and over - if the movie gave me something to chew on.  I save those for occasional viewings when I can really take them in.  I did not mean to give it 13 years between viewings.  Whoops.  But here we are.

These days, Wolf of Wall Street is mostly known as the source of a wide range of GIFs and memes.  Star Leonardo DiCaprio plays the real-life role of former stock hustler Jordan Belfort full-tilt, and screen grabs of some of his scenes are just plastered everywhere. If it's DiCaprio and he's not Gatsby, this is probably the movie that GIF came from.

This is one of those movies where I can see how it might have made some people unhappy.  But overall, the critical consensus was strong and I guess this did get some Oscar noms (or so Jamie told me).  It's a movie that is very loud about what it's saying, and still manages to never say it directly, and in that, I recall at the time of the movie's release people were being willfully obtuse, clutching pearls at the content of the film.

Let's be honest, this movie have the most nudity of any American movie of the past two decades.  It features out of control finance bros engaging in all manner of tsk-tsk behaviors from drug abuse to illegal stock trades to infidelity to the tossing of little people.  In fact, this movie opens on our leads doing the ladder.

Like many of Scorsese's movies, it's a look at America.  Not how we think of ourselves with rock, flag and eagle jingoism, but what we really value.  This is a movie that is happy to point out that the people we trust to enforce the law can hope for a livable wage and a pension, and all breaking a few hundred laws will do is get you into a summer camp of a prison for a couple of years.

But it's also showing how breaking those laws, how pushing the envelope is it's own reward.  You can treat people as Jarts.  You can include escorts as part of your business expenses and got to work so high you can't see, as long as you do it where no one can see and money is exchanging hands.  We're used to movies showing us the downside of excess, but this movie never really says that.  Instead, what it says is that hubris and bad luck are all it takes for it all to fall apart.  

That may not be as satisfying as "because of their evil deeds, the mighty were doomed to fall".  No, we know the reason our protagonist fell was just a series of unfortunate events - at least as the movie portrays it.  A premature death.  A storm at sea.  A Benihana executive up to no good.  But parties rife with coke and quaaludes and hookers?  That's just a good weekend, and schlubs like you and me and Kyle Chandler's FBI agent won't ever see any of that.    

The cast is fascinating to look back at 13 years later.  

Cristin Milioti showing what people would embrace a decade later.  McConaughey playing a maniac mentor.  Rob Reiner as his father (and Cristine Ebersol in a non-speaking role as Jordan's mother).  Jon Bernthal.  Kyle Chandler.  Jon Favreau.  Joanna Lumley.  Shea Whigam.  Oddly, two guys who were just in Coyote v. Acme appear, Kenneth Choi and P.J. Byrne.  This is a reminder of how good Jonah Hill is when he wants to be.  

This is, of course, how the notion of who Margot Robbie is became solidified in my mind.  I wasn't honestly expecting much, but as Robbie has proven - starting for me with this movie, and then a string of stellar performances (I'm the dude who loved Barbie,  I, Tonya and Gunn's Suicide Squad), Robbie has proven again and again, she is the real deal.  

And, as I said to Jamie when the movie finished - I'm pretty withholding in my praise for male actors.  I have my favorites, of course.  And this is deeply uncontroversial - but I genuinely think Leonardo DiCaprio is the best American male actor at this point.  He started strong with What's Eating Gilbert Grape? and by The Basketball Diaries, I was stunned.  If he has a problem, it's that I think he's the kind of actor who really does disappear inside of a character - he's not Ryan Reynolds where you kind of know what you're going to get (which is terrific.  I don't begrudge anyone that.)  But DiCaprio is a monster talent, and I don't think he hits a false note in this film, even when his character *does*.  

As we head into late 2026, there's something worth going back and looking at in this movie.  Because if you think these guys were having a good time then, imagine what's going on as the entire country gets turned into a casino.