3. Killers of the Flower Moon (2023)
DiCaprio and De Niro, despite both being Scorsese’s go-to guys, had only worked together once before this collaboration, but the wait was certainly worth it. In a film that’s top-heavy with as many A-listers as possible, it’s this high-wattage duo that dominates the frame as a silver-tongued cattleman and his not-so-bright, pathetically compliant nephew who methodically plot to eliminate the members of the oil-rich Osage nation in early-1920s Oklahoma.
Scorsese’s running preoccupation with the corrupting influence of greed on the human spirit fits perfectly into this true-life crime tale, which surprisingly finds its beating heart in the poisonous love that blossoms between DiCaprio’s Ernest Burkhart and Lily Gladstone’s Molly, a wealthy indigenous woman who can’t fathom the depth of the sins her backstabbing husband has committed.
As a man full of contradictions at the constant mercy of his domineering white supremacist uncle, DiCaprio manages to really sink his teeth into the role, going from caring to homicidal without a hitch as the members of the Osage tribe begin to drop like flies. It is a testament to his peerless range and skill to turn on a dime that his murderous halfwit still comes across as a real person and somehow manages to elicit our sympathy despite being way past the path of redemption. If nominations come calling, expect Leo to wiggle his way straight into the Best Actor race on his way to his sixth Oscar nod.
2. The Departed (2006)
This high-wire cat-and-mouse thriller, an English-language remake of the superb Hong Kong actioner “Infernal Affairs”, is always contextualized within Scorsese’s back catalog as just another case of the Oscars giving someone the night’s biggest prize as a sort of belated apology for past snubs.
Granted, even the most dedicated Scorsese diehard would have a hard time calling “The Departed” his finest hour, but unfairly pigeonholing the 2006 Best Picture winner as “the one that got him over the Oscar hump” tends to overlook the fact that it is, in fact, fiendishly entertaining even by the director’s benchmark. Mark Wahlberg, Matt Damon and Jack Nicholson are all given flashier roles and therefore earned the lion’s share of plaudits, but it’s DiCaprio actually holding the fort on this one with an understated yet beyond committed performance as Billy Costigan Jr. — a fresh-faced Boston cop who must walk a fine line between two worlds after going deep undercover in the Irish-American mob.
You can look at it as a companion piece to “Goodfellas” or judge it strictly on its own terms, but the point remains: this is the kind of rollercoaster ride (no pun intended) you just simply stop and watch whenever it’s on cable.
1. The Wolf of Wall Street (2013)
The biggest endorsement one can give of Leo’s career-defining turn as real-life investment huckster Jordan Belfort is that he plays his character with such devilish poise that it has now transcended film into the general consciousness as a symbol of greed, hubris and debauchery. Let’s, just for the purposes of this list, divorce the alarming number of lazy audience members and obnoxious frat boys that somehow came away with the idea that Scorsese endorses the same toxic finance bro culture he inarguably sets out to mock, from DiCaprio’s acting tour-de-force itself, which probably ranks as the most unforgettable performance in a career chock-full of them.
The actor dials it to 11 for virtually every scene as the titular stockbroker; a hedonistic, foul-mouthed and coke-fueled monster who cheated his way up through the ranks of the corporate banking world by defrauding would-be investors out of millions of dollars in the early ’90s. Anytime his character pops up on the screen, whether he’s rallying his loyal pack of power-hungry acolytes, bribing federal agents, dropping f-bombs, or crawling to his Lamborghini after taking one too many Quaalude pills, DiCaprio is in full movie-star mode, sucking up all the oxygen in the room and moving with an impossibly meteoric energy.
As “Goodfellas” and “Casino” taught us so memorably in the past, every douchebag who runs afoul of the law eventually gets their comeuppance. But part of what makes Scorsese’s pitch-black satire stick is that it casts its decadent anti-hero not as an anomaly but a natural symptom of a broader system that continues to allow two-bit scoundrels like Belfort to thrive, profit, and get off scot-free. Forget sacrificing himself to save Rose or being mauled by a grizzly bear — this is the high point of DiCaprio’s career.