Leonardo DiCaprio has distinguished himself as a Hollywood legend who has kept classy, selecting for hard parts with renowned auteurs such as Quentin Tarantino and Martin Scorsese — all the while pursuing humanitarian concerns through his prodigious environmental activities. DiCaprio portrayed a washed-up movie star at the end of his tether in "Once Upon a Time in Hollywood," which is possibly the largest leap yet for an actor with such an illustrious lineage and outstanding body of work.
DiCaprio is one of the few Hollywood actors working at the moment who consistently provides something worth watching, with roughly $3 billion in the worldwide box office to his reputation and a litany of choices that illustrate his discerning instincts each time out. While "Don't Look Up" may not be DiCaprio's finest work, the Oscar winner has given several memorable performances. We have chosen 11 of his greatest.
#1 The Wolf Of Wall Street
"The Wolf of Wall Street" is filmmaker Martin Scorsese's best cooperation with his 21st-century leading man, charting stockbroker Jordan Belfort's (DiCaprio) reckless, boisterous spiral into corruption and self-destruction starting in the late 1980s. DiCaprio gives his funniest and most devastating performance as Belfort, a megalomaniac for whom the road of excess leads to the palace of knowledge – the hard way. While Belfort is a despicable guy who embodies the worst inclinations of capitalist greed, DiCaprio takes on the risky mission of instilling pity in the man throughout, converting this cunning money-making machine into the ultimate contradiction of our difficult times.
#2 The Aviator
In Scorsese's Hollywood blockbuster, DiCaprio plays billionaire and aviation mogul Howard Hughes, tracking the Tinseltown magnate's slide on the path to Shakespearean proportions of power-grubbing and greed. Hughes' descent into obsessive-compulsive disorder, which would isolate those dearest to him, is painfully portrayed by the actor.
#3 The Revenant
DiCaprio's portrayal in Alejandro G. Iárritu's man-versus-nature epic is a savage yawp of performance, putting the star into pitiless circumstances in Calgary, Argentina, and the United States, as well as the intestines of a bear carcass. The actor isn't renowned for physically challenging changes, but "The Revenant" allowed him to push himself as an actor to new heights while still exuding the type of manly confidence for which he's always been known. He finally received his long-awaited Academy Award for Best Actor for his portrayal of a frontiersman suffering against the elements. As a riveting man-versus-nature journey, the film provided the ideal platform for DiCaprio's environmentally responsible campaign, which he recognized in his Oscar acceptance speech.
#4 Django Unchained
DiCaprio's desire to play the criminal was a risk, but he's dedicated to portraying an unforgivable hideousness as beguiling Candyland slave owner "Monsieur" Calvin J. Candie in Quentin Tarantino's revisionist slave narrative "Django Unchained" — so committed, in fact, that the actor gashed his hand open throughout a take and still stayed in character. In the following roles, DiCaprio avoided being typecast as the villain.
#5 Shutter Island
"Shutter Island," Scorsese's closest resemblance to a horror movie, provides a stage for DiCaprio as tormented U.S. Marshal Teddy Daniels. DiCaprio, as a man pursued by a dark history that is inextricably out of touch, keeps us dangerously balanced between reality and imagination, brooding through Scorsese's hallucinogenic set pieces to create a portrait of pained masculinity. The film's spooky, Val Lewton-inspired environment allowed the actor to access a level of inner torment that he had never displayed onscreen previously.
#6 Once Upon a Time… in Hollywood
In his second collaborative project with Tarantino, DiCaprio provides his most visually comedic portrayal to yet, a far cry from his nasty act in "Django." As Rick Dalton, the constantly soused Western star, DiCaprio adds empathy to his character's tough road as he ambles through the calm, breezy Los Angeles of 1969 — where calamity lurks just around the corner. Dalton is a wistful character who can't tell if he's genuinely in decline, and this enables the actor to give his performance a touch of sorrow that is utterly unique for him.
#7 The Departed
When it comes to Martin Scorsese's version of the 2002 Hong Kong thriller "Infernal Affairs," you can't help but pronounce it "The Depaaahted" because of DiCaprio's harsh depiction of Boston police school newbie Billy Costigan. Billy, played by Leonardo DiCaprio, goes through ups and downs on his path to corruption, which culminates with an unexpected boom. This gruff, testosterone-fueled portrayal, as much as Scorsese's passion in it, helped define this Best Picture winner's rough environment and represented a significant turning moment in the actor's cinematic presence development.
#8 Romeo and Juliet
In Baz Luhrmann's 1996 rendition of William Shakespeare's classic, DiCaprio is swooningly great, using his boy-next-door physical beauty and debonair charisma to represent the ill-fated Romeo Montague, opposite Claire Danes as his destined sweetheart. He was the personification of the 1990s teen idol in "Romeo and Juliet," blazing on all cylinders in a charming, tragic performance that revealed DiCaprio's brilliance to the public.
#9 The Basketball Diaries
DiCaprio played the poignant character of heroin-addicted basketball great Jim Carroll in filmmaker Scott Kalvert's dramatization of Carroll's book at the age of 21. With a brilliant ensemble that includes Lorraine Bracco and Mark Wahlberg, DiCaprio conveys the harm and manic desperation of heroin addiction with finesse. This is uncharted ground for any actor, but DiCaprio's ability to pull it off without obtrusive showboating offers a glimpse into the careful maneuvering which would continue to develop throughout his career.
#10 Revolutionary Road
Seeing Sam Mendes' stately Richard Yates version "Revolutionary Road" is like watching a marriage crumble in real-time, with Mendes' then-wife Kate Winslet clashing with DiCaprio amid the drab monotony of 1950s suburban Connecticut. Imagine Jack and Rose surviving the drowning of the "Titanic" and shacked up to follow the American dream, only to find the huge fat deception at its heart, and you'll have a taste of this nightmare. As the boozing, womanizing, chain-smoking Frank Wheeler, DiCaprio portrays suppression and remorse with a sneaky look and a cigarette flick.
#11 Catch Me If You Can
Steven Spielberg's slick version of master of deceit Frank Abagnale's autobiography stars a marvelously shifty (and extremely debonair) Leonardo DiCaprio as a person who worked as a doctor, lawyer, and pilot before the age of 18. With Tom Hanks' FBI agent Carl Hanratty constantly one step behind him, DiCaprio skillfully combines many acts into one. DiCaprio performs one precisely calibrated imitation after another with each new identity he wore, making the various faces he takes as captivating to the spectator as they are to the individuals in Frank's orbit who fall for his smarm and cajolery.