Get excited. Today is the day of the release of Martin Scorsese’s Killers of the Flower Moon which stars two of Scorsese’s frequent collaborators, Robert De Niro and Leonardo DiCaprio. To celebrate, what feels like a holiday, I’m going to rank the collaborations between Scorsese, De Niro, and DiCaprio. Overall, there are 14 total collaborations; nine featuring Robert De Niro and five featuring Leonardo DiCaprio.
Quick note, this is my ranking. This is my personal preference so don’t come for my head when I don’t have Taxi Driver at one or have The Aviator higher than it probably should be.
14. New York, New York (1977)
I’ve only seen New York, New York once in my life, and I don’t remember a lot from it. One thing I do remember though is that I wasn’t too fond of it. De Niro is good in it, but it’s an average collaboration in the pantheon of Martin Scorsese and Robert De Niro working together. It also hurts that this is sandwiched between Taxi Driver and Raging Bull — two of Scorsese’s most acclaimed pictures. I frankly find it forgettable, but if it’s your favorite congrats. That’s weird, but congrats.
2.5/5 Stars
13. Cape Fear (1991)
Quite possibly the scariest Robert De Niro character is Max Cady in Cape Fear. He’s gruff, intimidating, and vengeful, a common theme with a lot of Scorsese’s characters. A lot of Scorsese’s crime dramas are very clean and polished, but what works with Cape Fear and makes it different is that after you watch this film, you feel filthy. You feel as if you’re caked in a layer of grime and filth because of how vile Max Cady is. On top of that, you feel fear for Nick Nolte and his family because they’re being targeted by this menacing figure.
The reason I have this film so low on the list is because, outside of the characters being great, the plot isn’t anything special. If you lose these very interesting and well-written characters, you’re left with a half baked thriller.
3/5 Stars
12. Taxi Driver (1976)
That’s a live look at me dodging the flack I’m going to receive for having Taxi Driver this low. Look, I get if you have it higher or maybe even at number one, but Taxi Driver doesn’t resonate with me the same way other Scorese – De Niro collaborations do. I might be able to relate with Travis Bickle as I used to have a mohawk and enjoy driving around at night, but the film as a whole doesn’t hit me the same as The King of Comedy or Raging Bull.
I do think there’s an argument to be made that Travis Bickle is the most iconic De Niro character. Either Bickle or Jimmy Conway from Goodfellas. Even though he’d been in The Godfather Part II and Mean Streets prior to this, this was the role where De Niro established himself as a star and made audiences realize that there is great magic when Scorsese and De Niro team up. It’s a technical masterpiece, but again, not one that I’m huge on and haven’t rewatched in a while.
3.5/5 Stars
11. The Irishman (2019)
It’s Scorsese, Pesci, Pacino, and De Niro. If this had been his final film, it would have been the proper swan song for Scorsese as it covered a topic he’s passionate about and brought together some of the most pivotal actors of his career. Thankfully it’s not because Killers of the Flower Moon looks awesome.
The Irishman was a film I wasn’t fond of initially. I thought that the runtime was extensive, the de-aging was pathetic, and it didn’t move the needle in Scorsese’s career. Following a rewatch, I found it to be a great film in his filmography, especially the final hour. The final hour serves as more of a horror film rather than a crime drama because we see the realization of aging from Frank Sheeran and Russell Bufalino. They realize that they’re on the last legs of their lives and that what they did early in their lives sticks with them forever.
4/5 Stars
10. Shutter Island (2010)
I know that Shutter Island is a film Scorsese isn’t fond of in his career, but it does incorporate a divine Leonardo DiCaprio performance. Out of the five performances from DiCaprio in Scorsese movies, three of them have him descending into madness — Shutter Island, The Departed, and The Aviator. DiCaprio is really good at portraying that and Scorsese is great at directing it. Unlike The Irishman, I do feel like Shutter Island hasn’t aged well. When you go back and rewatch knowing the twist, you notice all the signs of what the twist is and you feel dissatisfied watching it. When you watch Se7en, The Usual Suspects, or Oldboy, knowing what the twist is doesn’t spoil the viewing. Maybe Shutter Island should be ranked lower, but DiCaprio is fantastic as Teddy Daniels.
4/5 Stars
9. The Departed (2006)
It’s true that you can enjoy a film, even though it has massive plot holes. That’s the case of The Departed. It’s not exactly a crisp script because there is NO WAY Costello would ever let a former cop into his inner circle. It is different in the case of Matt Damon’s character, Colin Sullivan because he was attached to Costello prior to becoming a cop. Every time I rewatch The Departed, I cringe at that idea because it’s so implausible. But then again, The Departed is extremely entertaining.
It’s insane to see and doesn’t happen often, but the young guns in this film, Mark Wahlberg, Leonardo DiCaprio, and Matt Damon act circles around the legends like Jack Nicholson, Martin Sheen, and Alec Baldwin. DiCaprio and Damon bring a great yin and yang parallel chemistry, while Wahlberg is an intensity generator. This isn’t my favorite collaboration between DiCaprio and Scorsese, but it’s pretty damn good.
4/5 Stars
8. Mean Streets (1973)
While I might prefer The Departed to Mean Streets, this was the film that made Scorsese who he is. It was him directing a genre of film that he is passionate about for the first time and it birthed the idea of Scorsese as a great director. That’s something Boxcar Bertha didn’t do for him. Mean Streets also serves as the first collaboration between Martin Scorsese and Robert De Niro. It’s a unique character that De Niro plays here and it’s kind of like the light beer version of De Niro in Cape Fear. He’s wild and somewhat care free like Max Cady minus the murderous tendencies. I don’t necessarily enjoy this more than The Departed or The Irishman, but with it being so influential in Scorsese and De Niro’s collaborating spree, I had to rank it a little higher.
4/5 Stars
7. Casino (1995)
“Well, tell me I was at least at the dinner. Allow me that much. Give me that much at least!” Ace Rothstein might be my second favorite character De Niro has every played in a Scorsese film. From the pastel colored suits to his bipolar adjacent attitude, I find him fascinating. Casino serves as one of the best scripts Scorsese has ever worked with, and De Niro as Ace Rothstein is the main vehicle for this scripts’ brilliant dialogue. And it’s the little moments that make a good script become a great script. For instance, when Rothstein chastises his baker for not putting an even amount of blueberries in muffins. That’s genius. We see a unique aspect of Rothstein and it only adds layers to him.
I do admire how Scorsese made another film about the mob, but didn’t make it a carbon copy of Goodfellas by heading out west. This easily could’ve been another New York mobster drama, but adding the aspect of being in a city like Las Vegas where stakes always feel higher and making it where De Niro isn’t exactly in the fold of the mafia makes this a refreshing and unique spin from Scorsese.
4/5 Stars
6. Gangs of New York (2002)
Here’s where more of my preface comes in and I’ll most likely be an outcast for having this take, but I think Gangs of New York is an awesome film with a ton of redeeming qualities. It features sweeping set pieces, extravagant battle scenes, and even though the run time is just south of three hours, I think it’s paced beautifully. One issue with having this on the list is that this doesn’t even feel like DiCaprio’s film. I mean, you could have put a scarecrow in his place and it wouldn’t have made a difference. And don’t perceive that as a knock on DiCaprio — it’s praise for the great Daniel Day Lewis. Maybe the most talented actor to ever live thrives in this period piece as Leo takes a backseat. Nevertheless, I love the ornamentation that Scorsese creates with Gangs of New York.
4/5 Stars
5. Raging Bull (1980)
If someone approached me and asked the question “What is Martin Scorsese’s best film from a technical angle?” I’d have one answer and one answer only. It wouldn’t be Goodfellas, nor would it be The Wolf of Wall Street. It’d be Raging Bull. From the methodical pacing going through the life of the shaky Jake LaMotta, you kind of sit back and gaze upon the masterful work from Scorsese. His camera work is pristine and the editing from his long time collaborator Thelma Schoonmaker might be the best of her career.
While I mentioned earlier that Travis Bickel in Taxi Driver is De Niro’s most iconic character and Ace Rothstein in Casino is one of my favorite De Niro characters, his best performance in a Scorsese film is here in Raging Bull. To be able to play the early stages of Jake LaMotta’s life where he’s the next best thing in boxing to playing him in his later life where he’s a has-been with a criminal record is pure art. Showing the highs and lows of someones life can’t be easy for an actor and he did it in an amazing way.
4/5 Stars
4. The Aviator (2004)
Much like Gangs of New York, I enjoy The Aviator far more than the masses. The first time I ever watched it, the 170 minute runtime intimidated me, but I was blown away. I find Leonardo DiCaprio to deliver an awe-inspiring performance because at this time in his career, he’s leaving the “heart throb” stage and is taking very serious roles like Gangs of New York and Catch Me If You Can. But then he follows up with The Aviator which is a deep and layered role, and that’s due to Howard Hughes being a deep and layered individual.
A lot like De Niro’s portrayal of LaMotta, DiCaprio encapsulates the monumental highs and extreme lows of Howard Hughes’ life. Whether it’s making big scale films with frills, crashing his planes one too many times, or battling with Juan Trippe, you’re invested. I don’t think another actor at this time could make me feel this invest. The only exception would be Daniel Day Lewis, but DiCaprio captures the whizz kid days of Hughes just as well as the depressing later moments of his life when OCD co-opts him.
4.5/5 Stars
3. Goodfellas (1990)
What can be said about Goodfellas that hasn’t already been stated. It’s probably Scorsese’s finest work and while De Niro brings a veteran presence to the screen, this film birthed the career of the late great Ray Liotta. There are many reasons to love this film, but the one that caught me the first time I ever viewed it was the soundtrack. Scorsese finds the perfect song for every moment, whether it’s using Then He Kissed Me when Henry and Karen enter the Copacabana or just utilizing artists like Aretha Franklin and Tony Bennett, it’s perfect.
One of the all-time great debates is what mafia film is better, The Godfather or Goodfellas. While they are very different and tremendous in their own ways, I will always lean Goodfellas. The reason being is that this is a 145 minute rollercoaster of highs and lows. From being a high roller with a closet full of cash and dignified suits to being drugged up and running from his paranoia, Henry Hill’s story is wild. Scorsese portrays it better than anyone could have ever done. That’s why he’s the greatest.
5/5 Stars
2. The Wolf of Wall Street (2013)
In the same vein of a film like American Psycho, there are two groups of people who like The Wolf of Wall Street. Those who understand the satire of it and get that Scorsese is poking fun at the ridiculous life style of people like Jordan Belfort, or those who idolize the likes of Jordan Belfort and Donnie Azoff. The individuals who idolize those people are the ones who give The Wolf of Wall Street a bad rap. But then there’s the crowd who loves to throw digs at this three hour thrill ride because it’s a “finance bros film“. The Wolf of Wall Street is fantastic and if one scene can encapsulate the mania that Scorsese brings, it’s the scene where Belfort takes the quaaludes and drives to the country club. Seeing him near crippled on the ground trying to make a call is hilarious and begins Belfort’s spiral.
Stylistically, The Wolf of Wall Street is interesting because of how vibrant it is. One of the first scenes is Belfort’s monologue and he’s driving speaking to the camera. While he’s driving, the different sports cars keep changing make, model, and color. It’s a smart choice because it flaunts the exuberant life style Belfort had. Along with that is another Scorsese soundtrack sensation. With Movin’ Out by Billy Joel, Mrs. Robinson by The Lemonheads, and Pretty Thing by Bo Diddley, it could feel messy and all over the place, but that fits the narrative of Belfort’s life. It’s all over the place.
While Matthew McConaughey was amazing in Dallas Buyers Club, I think DiCaprio should have won the Oscar for Best Actor at the 86th Academy Awards. It’s probably his best performance due to the high energy brought to the screen and the way he became Jordan Belfort was interesting to gaze at.
5/5 Stars
1. The King of Comedy (1982)
Ladies and gentlemen, Rupert Pupkin — “Good evening, ladies and gentlemen. Let me introduce myself. My name is Rupert Pupkin. I was born in Clifton, New Jersey… which was not at that time a federal offense. Is there anyone here from Clifton? Oh, good. We can all relax now. I’d like to begin by saying… my parents were too poor to afford me a childhood. But the fact is that… no one is allowed to be too poor in Clifton. Once you fall below a certain level… they exile you to Passaic. My parents did put the first two down payments on my childhood. Don’t get me wrong, but they did also return me to the hospital as defective. But, like everyone else I grew up in large part thanks to my mother.”
Not just my favorite Scorsese or favorite De Niro film, but one of my all-time favorite films. Perhaps the greatest dark comedy ever, Scorsese masks the plot of a psychopathic comedian with humor and makes you like the outcast Rupert Pupkin even though he’s a criminal who does stalk and kidnap Jerry Langford. It’s brilliant because we shouldn’t love this whacko. BUT WE DO.
I do think an underrated aspect of the Rupert Pupkin character is that even in his own mind, he’s a hack comedian. When he’s fantasizing about having dinner with Langford and the girl asks for an autograph and says “My name is Deloris” and he turns back and tells an all-time bad joke “Deloris? That was my father’s name.” Him not being a good comedian on top of him being a madman stalker is the cherry on top of this masterclass from Scorsese. The film is so great, that in 2019 Todd Philips ripped it off when he made Joker.
5/5 Stars
