Martin Scorsese and Leonardo DiCaprio make up one of Hollywood's biggest dream teams, but how do their collaborations stack up from worst to best? In truth, there's not a bad apple in the bunch, and since 2002 the duo has gifted audiences five films as varied in style and subject matter as can be. As their latest collaboration, Killers of the Flower Moon, gears up for production, and in the month of the 11th year anniversary of their 2010 film Shutter Island, it's worth taking a look back at what this prestigious match-up has turned out thus far.
Martin Scorsese is often celebrated as one of the greatest living American filmmakers, with films as diverse as gangster flicks What's Eating Gilbert Grape. It was his role in 1997's Titanic, however, that turned him into one of Hollywood's biggest heartthrobs, a sex symbol on par with James Dean or Elvis Presley. In a way, his entire career since then has been an attempt to escape that typecasting, finally leading to him winning an Oscar in 2018 for The Revenant.
His maturation from teen dream to Academy Award winner can largely be tracked in his t efforts with Scorsese. Their quintet of collaborations amassed four Best Picture and Best Director nominations and one win in each category, with two Best Actor nominations for Leo himself. Judging them "worst to best" isn't necessarily fair; rather, these have been arranged from pretty good to exceptional.
Gangs of New York
Marty and Leo's first collaboration was actually a bit transactional in nature; DiCaprio would lend Scorsese his high-wattage movie star personality to produce a film the director had been dreaming about since the 1970s, and Daniel Day-Lewis' galvanizing performance as William "Bill the Butcher" Cutting.
That delectable, scene-stealing and scenery-chewing performance is the major reason to revisit Gangs of New York, along with the art direction by Dante Ferretti, which painstakingly recreates over a mile of mid-19th century New York, and the wonderfully-detailed costumes by Sandy Powell. It's a typically ambitious Scorsese film, and credit must be given to him for fighting to maintain his original vision against the now-disgraced producer Harvey Weinstein. Still and all, its slight revenge-centered plot doesn't really warrant its near-three-hour run time.
The Aviator
Gangs may have been Leo's first foray into more adult roles, but it would be his next Scorsese collaboration that would cement his arrival as a bona fide, mature movie star. In The Aviator, Leo plays billionaire aviation tycoon and Hollywood filmmaker Howard Hughes, in a performance that would garner him his first Oscar nomination since his child star turn in What's Eating Gilbert Grape. A Hughes biopic had been something of a cinematic Moby Dick for many of Hollywood's biggest directors, from Warren Beatty to Steven Spielberg, Brian De Palma to Christopher Nolan. Thankfully, it's a project that finally found a home with DiCaprio and Scorsese, in a film that cemented their partnership as one of cinema's greatest.
In direct contrast to his strained turn in Gangs, then-29-year-old Leo carries this whole movie on his shoulders like an old pro. It's a bit hard to buy into his eventual transition to playing 40, but what he does sell completely is the depressive transformation that would have him spending the second half of the film locked away in a dark room, watching old movies, and peeing into jars. The OCD-ridden hellscape Leonardo DiCaprio portrays in this latter part of the film is truly harrowing, the result of a reportedly exhaustive research process that inspired, among other things, a disturbing scene where he washes his hands so much they begin to bleed. From his youthful, bright-eyed opening scenes to a chilling finale where he locks eyes with himself in a mirror and repeats in haunting intonations, "Come in with the milk, come in with the milk," Leo leads The Aviator with his signature commitment and surprising sensitivity.
The Wolf of Wall Street
Ever the versatile filmmaker, Martin Scorsese followed up his lone children's film Hugo with his most explicit and profane. Looney Tunes short. It's an excessive performance in a film about excess, and while that intellectually feels correct, it inevitably rubbed many audience the wrong way, as many deem it a glorification of this kind of behavior.
But this said, Scorsese seems to attack Jordan and his merry band of maniacs with more contempt than he ever displayed for the mobsters of his earlier works. He wisely frames The Wolf of Wall Street like a party, a wild bacchanal, and while the result can come across to some as 180 minutes of crass, somewhat one-note satire, it's fun to see the then-71-year-old filmmaker crafting his most kinetic, vibrant movie since 1990's Goodfellas.
The Departed
After nominations for played by Jack Nicholson in a performance that's either a captivating display of malevolence or an over-cooked slice of ham (perhaps a bit of both).
Leo, on the other hand, is asked to keep more of a lid on things, and in turn, gives one of his best performances. His attempts to keep it cool and not betray the cracks of panic forming as he worries Frank will find out his true identity simmers his often "big for the sake of big" choices down to a low boil, and Billy's anxiety is so captivatingly portrayed that it feels like both he and the audience might wind up with a heart attack. Of course, by the movie's end, he's just another corpse in the film's astonishing body count, while The Departed remains living proof that this collaboration is far from dead.
Shutter Island
Dumped by Paramount in a February wasteland far from the awards season potential this film ultimately had, and overshadowed by Inception - that other 2010 Leo-led vehicle with a complex narrative and plenty of ghostly flashbacks involving a mysterious wife - this psychological thriller adapted from a Dennis Lehane novel was initially dismissed by some as "lesser Scorsese." While Shutter Island was the actor and director team's highest-grossing film until The Wolf of Wall Street, it's also their least well-reviewed, with a 68% on Rotten Tomatoes. 11 years on, however, time has been kind to this haunting gem, and in of the marriage between this maestro and movie star, it's the best they've yet done.
The initial appeal of the film seemed to be "Scorsese does horror," a genre into which he'd not yet dipped his toe. Indeed, he creates an undeniable mood, evoking Hitchock with Robert Richardson's shadowy, claustrophobic cinematography and a Robbie Robertston-curated score of modern classical music as beautiful as it is bone-chilling. Leo is a game participant in the throwback vibe, donning a thick townie accent as Teddy Daniels, investigating a patient disappearance at the Shutter Island Asylum for the Criminally Insane. Soon enough, however, Scorsese peels back the genre artifice with a stomach-churning twist: Teddy isn't a detective at all, but the island's most dangerous patient, victimized by a broken mental health care system's cruel role-playing game.
Chiller becomes a character study, and a genre playground becomes the setting for an exploration of grief. DiCaprio's movie star swagger, so capably deployed as the cocksure detective, instantly deflates in a flashback which may be the best scene of his career. Returning home one day, he finds that his wife, herself a victim of mental health problems, has drowned their three children in a pond. Wracked with sickening despair, Leo swims desperately into the waters, gathering together the floating corpses in a nakedly emotional display of stomach-churning impotence. Scorsese's camera lingers painfully, uncomfortably, on DiCaprio's warped, red, tear-streaked face, and at that moment the potential of their Gangs collaboration becomes realized fully. With Shutter Island, Scorsese turns a genre exercise into a painful condemnation of the mental health care system, and DiCaprio takes his place as the movie star with a soul he's always strived to be.
