It’s crazy to think that Leonardo DiCaprio has been one of our biggest movie stars for three decades already. Over the course of his career, the 48-year-old actor has reinvented himself many times over — stretching back to his early days as a teen heartthrob and perennial Oscar contender to his newfound role as a high-profile activist — all while being courted by the entire industry as one of Hollywood’s most bankable stars.
Ever since he was speed-injected into the mainstream with 1993s “What’s Eating Gilbert Grape”, DiCaprio has established himself as a one-man brand with enough pull to put asses in seats and turn movies into global events on his name alone without ever having to don a cape, suit up in spandex, or do crazy stunts. Despite turning down too many lucrative roles to name, he’s crafted the most consistent and diverse resume of all his peers by opting to work almost exclusively alongside Hollywood’s finest directors, including Steven Spielberg, Quentin Tarantino, James Cameron, Christopher Nolan, Alejandro G. Iñárritu, and Clint Eastwood, to name a few.
DiCaprio’s latest film, “Killers of the Flower Moon”, marks the sixth time the actor has teamed up with Martin Scorsese. An adaptation of David Grann’s non-fiction bestseller of the same name, the star-studded crime epic depicts the serial murder of members of the oil-wealthy Osage Nation in early-1920s Oklahoma. So, in light of the much-anticipated movie finally hitting theaters before its arrival on Apple TV+ this fall, we’re looking back on one of Hollywood’s defining creative partnerships since the turn of the century.
6. Gangs of New York (2002)
The Scorsese-DiCaprio axis got off to a shaky start with this richly detailed but bloated 19th century period epic, a long-gestating passion project based on a book by Herbert Asbury that the director had kept on the back burner since the seventies before a troubled production saw him go over budget and wage war against Miramax honcho Harvey Weinstein.
DiCaprio, perhaps a bit too eager here to shed his Titanic-era matinee idol status, wasn’t afraid of stretching himself as an actor taking on the role of revenge-seeking Irish immigrant Amsterdam Valley, who returns to the gang-ridden intersection of lower Manhattan known as the Five Points to avenge the murder of his father at the hands of Daniel-Day-Lewis’ Bill the Butcher.
Though the film pivots around DiCaprio’s nominal lead character, “Gangs of New York” so often belongs to the second-billed Day-Lewis, who carries the entire movie on his shoulders going from friendly to sinister within a moment’s notice as the mustachioed Bowery Boy gang leader — an electrifying turn that would land him his third Oscar nomination.
5. The Aviator (2004)
DiCaprio fared much better in his second go-round with Scorsese, which found the former teen heartthrob stepping into the shoes of Howard Hughes in this lavish, star-packed tentpole. The then-29-year-old star excels at compartmentalizing the eponymous character’s inner turmoil and sense of solitude, as we watch the same man who once became a larger-than-life celebrity, billionaire mogul, eccentric film producer, and aviation magnate during the 1930s decade slowly succumb to his demons and obsessive-compulsive disorder.
It’s a delicate balancing act to pull off, but Leo channels Hughes’ many contradictions and layers, skillfully transitioning from baby-faced all-American genius with boundless ambition and indefatigable charisma to paranoid recluse spiraling into madness. It’s tempting to bump this film up a few spots solely on the basis of DiCaprio’s Oscar-nominated turn — some would argue he’s never been better under Scorsese’s stewardship — but that isn’t enough to overlook the bloated runtime and rather dull stretches of the story, both of which make “The Aviator” stick out like a sore thumb within the director’s own back catalog.
4. Shutter Island (2010)
Scorsese surprised many when he leveraged his Hollywood clout after storming the festival circuit with “The Departed” into shooting this pulpy Hitchcockian mystery based on a potboiler novel by Dennis Lehane, which went on to rack up nearly $300 million worldwide to become his highest-grossing project to date.
Though nowadays widely regarded as a “one for them” genre fare constructed for mass appeal, “Shutter Island” is a brilliant showcase for DiCaprio to flex his acting chops as Edward “Teddy” Daniels, a U.S. Marshal who comes home from serving in WWII only to plummet down the rabbit hole of self-deception after being charged with investigating the disappearance of a patient from a mental asylum in a secluded island.
Ambiguity is the name of the game in this neo-noir-esque exercise in genre filmmaking that thrives in building tension and manages to keep the viewer guessing at every turn. DiCaprio, who dominated the 2010 blockbuster scene by also starring in “Inception” later that summer, proves particularly adept at playing a deluded man hopelessly haunted by his past. One can debate whether the film’s last-minute rug-pull moment works or not, but it does make it the least rewatchable of the bunch.