Leonardo DiCaprio returns to the big screen this weekend in Paul Thomas Anderson’s One Battle After Another, and it’s shaping up to be another critical win for one of the best actors of his generation. DiCaprio has always had a great eye for picking the right films that showcase his talent, but with a filmography as impressive as his, it could be hard to pin down some of his best work. As he’s gearing up to grace our screens again this weekend, this felt like the best time to dive into DiCaprio’s five best performances that prove he’s a true cinematic acting legend.

Honorable Mention: What’s Eating Gilbert Grape (1993) as Arnie Grape

DiCaprio was just a teenager when he took on the role of Arnie Grape in What’s Eating Gilbert Grape, but he proved early on that he had the emotional maturity to take on a particularly difficult role. Johnny Depp may have been taking the lead here, but as his mentally disabled young brother, DiCaprio steals every single moment he’s on screen and portrays his disability with grace, without turning the role into an offensive caricature. DiCaprio earned his first Academy Award nomination for his performance in the Best Supporting Actor category at the age of 19, making him one of the youngest nominees to do so.

5. Django Unchained (2012) as Calvin Candie

Sometimes you can tell when an actor is taking on a role with absolute relish, and DiCaprio does just that in Quentin Tarantino’s Django Unchained as Calvin Candie. It’s a villainous turn for the actor, and he proves that he can portray someone purely evil without any shades of grey. He’s Southern entitlement personified as the owner of the Candyland Plantation, mixing undeniable charm with an unflinching menace where his slaves are forced to engage in brutal wrestling matches. DiCaprio earned a Golden Globe nomination for Best Supporting Actor for his performance, but he missed out on an Academy Award nomination, which still stands as a pretty egregious snub for some of his best work.

4. The Departed (2006) as Billy Costigan

In 2006, DiCaprio had a stellar year with both The Departed and Blood Diamond hitting the big screen, and although he ultimately earned an Oscar nomination for his work in the Edward Zwick film, his work in Martin Scorsese’s Best Picture winner is not to be overlooked. As a state trooper who dives into the worst of Boston as he goes undercover in the Irish Mob, DiCaprio sells a sense of nervousness and panic as his situation escalates to a fever pitch.

It’s an emotionally complex role, and it can arguably be described as the actor’s first “grown-up” turn, something he dives into with ease for this third of many collaborations with Scorsese. This becomes another Academy conundrum for DiCaprio since it’s believed that Warner Bros. campaigned for the actor in the Supporting Actor category to avoid conflict with his lead role in Blood Diamond. The Departed was littered with performances that stood out, and given its ensemble nature, it can be argued that it features a collection of top-notch supporting performances.

At the Golden Globes, DiCaprio was double-nominated in the lead actor (drama) category for both The Departed and Blood Diamond, while he earned a Supporting Actor SAG nomination for the former. The Academy doesn’t allow you to be double-nominated in the same category, which also led to the decision to submit DiCaprio for supporting. His co-star Mark Wahlberg ultimately secured the Best Supporting Actor nomination, but DiCaprio’s performance definitely deserved a spot.

3. Once Upon a Time in…Hollywood (2019) as Rick Dalton

DiCaprio teamed up with Tarantino again in this tale of an actor not at the height of his fame during a pivotal year for the film industry in 1969, which also coincides with the Tate murders on Cielo Drive. As an actor, DiCaprio has never come close to fading away, but it felt like he genuinely connected with Rick Dalton’s crisis of being an actor at a crossroads in his career. DiCaprio dives into the role with distinct honesty, managing to be charmingly funny in one breath and selling his feelings of professional insecurity in another.

The actor is also aided by an effortless chemistry with his co-star Brad Pitt, who plays his more cool, calm, and collected stunt double, Cliff Booth. They play off each other with ease and showcase why they’re among the best in the business at what they do. DiCaprio earned another Academy Award nomination in the Lead Actor category for his work here, but ultimately lost out to Joaquin Phoenix’s stellar work in Joker. Some believe that since DiCaprio (finally) won in 2016 for The Revenant, the Academy believed it best to let Phoenix have his moment, but had DiCaprio won, there would’ve been no surprised reactions in that room on Oscar night.

2. The Aviator (2004) as Howard Hughes

DiCaprio has never flinched at portraying emotionally complex people, but it might not get more complex than his portrayal of real-life billionaire Howard Hughes in Martin Scorsese’s The Aviator. Despite being in his late 20s when the film was in production, DiCaprio makes the audience believe his turn as the pioneer of aviation across 20 years, as he also battles with an obsessive-compulsive disorder that gradually consumes every aspect of his life.

It’s no surprise that DiCaprio earned his first Lead Actor Academy Award nomination for his work in the film because it’s a performance that proves the actor’s commitment to his craft. He expertly portrays Hughes at his very best while also being tragically brilliant when he has to showcase Hughes’ mental decline. Scorsese clearly saw DiCaprio on the verge of accessing his best potential during their first outing together in 2002’s Gangs of New York and pushed him to embrace it in The Aviator.

1. The Wolf of Wall Street (2013) as Jordan Belfort

DiCaprio took on a very different real-life figure as Jordan Belfort in Martin Scorsese’s The Wolf of Wall Street and scored his best performance to date. The actor has never really done what many would call a straightforward comedy, so this might be the closest we get to DiCaprio flexing his full comedic chops as Belfort, a man consumed by wealth, embedded in corruption, and someone embracing all the excess that comes with it. The decision to take a more satirical approach to the life of Belfort proved to be a wise decision because it allowed DiCaprio to somehow make a not-so-great human being come off as someone who was interestingly likable, despite all of his misdeeds.

Whether he’s spouting off his unforgettable all-staff monologues, engaging in combustible chemistry with Margot Robbie, or trying to crawl to his car while high on quaaludes, DiCaprio is unwavering in his commitment. The actor received another Lead Actor Academy Award nomination for his performance, but would lose out to Matthew McConaughey for his work in Dallas Buyers Club. It would’ve been great to have seen DiCaprio walk away with the trophy for this performance, but he didn’t need an Oscar win to prove that this is his best big-screen turn in a sea of other captivating performances that have more than solidified his place as one of the best actors working today.

One Battle After Another opens nationwide this weekend.

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