The Revenant.From Everett Collection.
When you get to be as famous as DiCaprio, at a certain point, you can do what you want. His collaborations with Scorsese neatly chart that evolution. During DiCaprio’s early-2000s period of creative drought, he and the director met on Gangs of New York, a fraught production overseen by Harvey Weinstein, before thriving on the studio-backed dramas The Aviator (Miramax), The Departed (Warner Bros.), and Shutter Island (Paramount). However corporate the machines were—something Scorsese has expressed regret about on his latest press run, from Weinstein’s Gangs meddling to the artistic limitations of Shutter Island—this was still Scorsese, and so DiCaprio operated in fresh shades of gray, tough morality dramas that challenged his sparkly persona. It’s no coincidence that his first Oscar nod since being recognized for the 1993 breakout What’s Eating Gilbert Grape came over a decade later, for his intense portrayal of Howard Hughes in The Aviator.
In that era, DiCaprio also dabbled in transformative villainy, whether with the heavy prosthetics of Clint Eastwood’s J. Edgar or the nasty twang of Tarantino’s Django Unchained. But Scorsese’s first independently financed production starring DiCaprio officially turned the actor’s appeal inside out. His very presence in The Wolf of Wall Street, as the sleazy stockbroker Jordan Belfort, presented a brilliant challenge. For three full hours, viewers were stuck in his manically depraved world, which DiCaprio embodies fearlessly and, at times, grotesquely—trading his limitless audience goodwill for a discomfiting repulsion. It’s why critics at the time often considered the film to be in conflict with itself, on the brink of valorizing its despicable protagonist. Of course, Scorsese’s intention was exactly the opposite. DiCaprio was almost too good. Perhaps some weren’t ready.
Don’t Look Up, Killers of the Flower Moon, Once Upon a Time in Hollywood.From Everett Collection.
A decade later, Scorsese and DiCaprio meet again in Killers of the Flower Moon, with the latter in a fresh career phase—one less burdened by the peak of fame, perhaps, and thus less in need of subversion. How quickly things can change: The pathetic, weaselly skin of Ernest Burkhart, a dopey war veteran unwittingly entangled in a horrific conspiracy to extort and murder the Osage community in 1920s Oklahoma, fits him like a glove. The film begins as a kind of sweeping love story between Ernest and an Osage woman named Mollie (Lily Gladstone), then develops into a searing horror movie about his involvement in the deadly poisoning of her and her family. His mob-boss-esque uncle, William Hale (Robert De Niro), pulls the strings, but it’s Ernest’s utter indifference toward stopping him, and protecting those he’s destroying, that marks the film’s most insidious and tragic form of evil.
Gangs of New York, Shutter Island, The Departed.From Everett Collection.