Jeremy’s Tophunder №14: The Wolf of Wall Street

8 min readJun 2, 2020

The Wolf of Wall Street is Martin Scorsese’s unconscious attempt to re-make Goodfellas in the 21st century.

The Wolf of Wall Street is not nearly as good a movie as Goodfellas.

I like The Wolf of Wall Street way more than I like Goodfellas.

This is another one of those instances where the quality of the movie and how it compares quality-wise to other movies in the same tone or genre doesn’t really impact how much I enjoy it. Goodfellas is, objectively, a masterpiece. The Wolf of Wall Street is a bloated, cartoonish version of Goodfellas, simply swapping out gangsters for stockbrokers and taking on a more intentionally comedic tone.

So why do I like it more? Exactly that reason. It’s bloated and cartoonish and funny. The opulence and excess of the characters isn’t a distraction from the story — it is the story. It’s just an incredibly fun movie. It thumbs its nose at everything, including its own narration.

On multiple occasions, Leonardo DiCaprio (as Jordan Belfort) interrupts himself in the middle of direct-to-camera 4th wall-breaking narration to dismiss what he’s saying as overly complicated. He then proceeds to explain the part you need to understand with all the grace of a sledgehammer.

I liken these moments to the celebrity cameos from The Big Short, and not just because they both deal with financial concepts— the movie needs to convey a complicated topic to an audience that probably won’t understand it. But, knowing that the audience won’t understand it allows the movie to take an unorthodox approach in explaining it. The Big Short opted to explain them as simply as possible in an absurd way, The Wolf of Wall Street opted to just eschew any real explanation and cut to “this is illegal” and “this made us rich.” Honestly, I think it’s a rather elegant method, kind of like watching a child come up with a simple solution that the adults in the room never would have thought of.

Part of the reason it works is because Leo is just so goddam charismatic and captivating, even when playing a swindling criminal. This came up a bit when I talked about his performance in Django Unchained, but it’s on display even more here simply as a byproduct of Belfort appearing in just about every scene of the movie. You can’t help but kind of root for him.

It doesn’t hurt that he seems (mostly) normal at the start of the movie. He’s a fresh-faced, wide-eyed rookie on Wall Street in the late 80s, who just seems excited to get to go to lunch with his boss (played spectacularly by Matthew McConaughey). If he had strolled into the room acting like he owned the place, I think the audience would have reviled him even more. But you kind of get sucked down this path with Jordan, as McConaughey suggests he needs to (a) drink more, and then expressly prescribes him to (b) masturbate more, and (c) use cocaine.

It’s an absolutely ridiculous scene, for two reasons. First of all, just look at McConaughey. He’s making weird noises and mostly speaking gibberish, and somehow none of it feels forced. He’s in like, two scenes in this movie (both in the first 20 minutes or so), and somehow he’s probably my favorite character. I want to see an entire movie of just him. Second, look at DiCaprio compared to who he becomes later in the movie. He’s noticeably uncomfortable with most of what McConaughey is saying, and yet, not too long after this, he’s popping quaaludes and cheating on his wife and screaming motivational speeches to his staff.

I’ve made the mistake of watching the real-life Jordan Belfort in interviews. I really can’t stress this enough — the guy is a scumbag. He exudes just pure contemptible energy and has an exceedingly punchable face. It’s truly incredible that DiCaprio was able to make him seem even vaguely likable for any length of time. When you watch actors portray the insane and unbelievable shenanigans that these people get themselves into, it seems fun and entertaining. But to hear the actual people describe those events is honestly kind of revolting, mostly because it doesn’t seem like they think they did anything wrong, other than get caught for the crimes they committed. To watch the movie knowing how much truth is behind the story really makes me appreciate how well DiCaprio and Scorsese and screenwriter Terence Winter were able to construct an actually engaging story out of it.

On the other hand, it also brings up the idea that these are people that shouldn’t receive any recognition, and spinning the story into some kind of wacky black comedy glorifies everything that happened. I think to some extent, that’s fair. I don’t disagree with that assessment. But I think there might be a double standard. There are plenty of movies that glorify criminals (some of which have been directed by Scorsese himself) and otherwise grimy characters, and most of those movies are celebrated rather than criticized. To draw parallels again to Goodfellas, Joe Pesci’s character is based on a real person, who committed real murders. Same goes for Robert De Niro’s character. Murder is a far steeper crime than securities fraud, but from what I see, there are more depiction-based criticisms of Wolf of Wall Street (or movies like it) in 2020 than there are of Goodfellas (or movies like it).

Regardless, I’d argue that The Wolf of Wall Street isn’t exactly glorifying the people involved. It’s airing all of their dirty laundry, and in the end, they all get pinched. Sure, they don’t spend nearly as much time in jail as they probably deserve, but that’s something to take up with the criminal justice system, not the people that made a movie. I certainly don’t walk away from the movie wishing my life was like Jordan Belfort’s. I suppose it would be nice to have millions of dollars lying around the house, but I don’t think I’d be a huge fan of being a degenerate drug addict who loses his wife and kids.

Overall, Scorsese crafts a really amazing movie. Beyond Matthew McConaughey’s amazing cameo, the movie also gets a great cameo from Spike Jonze (as the guy that offers Leo a blowjob if he can sell thousands of dollars off the pink sheets) and another from Rob Reiner (as Leo’s apoplectic father). But the most pleasantly surprising performance in the movie comes from Jonah Hill. Hill apparently made just $60,000 for the movie (the minimum allowed by SAG at the time) because he so desperately wanted to be in a Scorsese movie. And really, he submits the best work of his career. He’s hysterical in the crack-smoking scene, and maybe even funnier on quaaludes at the pool party. If you’re looking for one ten-minute supercut of all of Hill’s best scenes, don’t worry, the internet has you covered. His Oscar nomination was well-deserved, although he probably never had a prayer of winning going up against Jared Leto in Dallas Buyers Club.

Both the crack scene and the quaalude scene linked above also highlight one of my other favorite elements of the movie — the unusual musical cues that Scorsese used to punctuate a few scenes, mostly involving drugs. My favorites, though, are both “Hey Leroy, Your Mama’s Calling You,” by Jimmy Castor, which plays at the end of Leo’s intense speech before the Steve Madden IPO, and The Lemonheads cover of “Mrs. Robinson” when the FBI finally comes to bust everyone at Stratton Oakmont (including a signature awesome Scorsese tracking shot). Scorsese always uses music really well in all of his movies, but I thought it really stood out here in a memorable way.

Ultimately, The Wolf of Wall Street is just an incredibly fun movie, maybe the most fun of any Scorsese work. It’s amazingly epic in size and spectacle, but somehow remains relatively focused on Belfort and his descent into mayhem and white-collar crime. It’s tough to say how much of the story is factually correct, mostly because the movie is based on Belfort’s memoir, and he strikes me as the kind of guy that would exaggerate, and a lot. But in terms of the story that Belfort set forth in his book, I feel like the movie stays pretty true to the story they know.

Is this Scorsese’s best work? Not even close. But it’s enjoyable. I have fun every time I watch it, which is something I can’t exactly say for Raging Bull or Taxi Driver, or even Goodfellas. I appreciate Scorsese movies as much or more than I appreciate the work of any filmmaker, but for me, The Wolf of Wall Street is Scorsese’s perfect marriage between a movie that is Great and a movie that is Fun.

(For a refresher on the project, I introduced it in a Facebook Post on Day 1)

Here’s our progress on the list so far:

2. A Few Good Men

3. The Social Network

4. Dazed and Confused

6. The Fugitive

7. The Dark Knight

8. The Departed

9. Saving Private Ryan

11. The Big Short

12. The Prestige

13. The Lord of the Rings: The Fellowship of the Ring