Leonardo DiCaprio takes more time between performances than he ever has these days; his latest release, One Battle After Another, will only be his third role in a feature film in a span of five years. But as a younger man, he gave us a host of iconic performances, and we’re here to discuss some of our favorites. Let us know what your favorite it @SiftPop!

Who would have thought a story centered around the struggles and greed of smuggling could lead to such a beautifully inspiring character arc? In Blood Diamond, Leonardo DiCaprio delivers an outstanding performance, seamlessly navigating emotional moments and intense action, and embodying a compelling accent. You genuinely feel that Danny’s motivations to help Solomon Vandy (Djimon Hounsou) stem from his desire to capitalize on the diamond Solomon buried. Danny’s transformation by the end is both meaningful and profound. Though I’m typically not a fan of the trope where the antihero experiences a sudden change of heart, here, it unfolds in a way that aligns perfectly with the film’s gritty tone, making Danny’s evolution both surprising and impactful. The choice to have him sacrifice himself for doing what’s right is a testament to the authenticity of the story. Unlike typical Hollywood narratives, where the hero often gets the girl, this story reflects that virtue is not always rewarded. While Forest Whitaker’s performance in The Last King of Scotland was remarkable, DiCaprio truly deserved the Oscar for this performance. (John Tillyard)

To pull off the story of con man Frank Abangale Jr. at the heart of Catch Me If You Can, charisma is a must. So it’s no surprise that Leonardo DiCaprio shines as the swindler with a smile. It’s right in that transition period where DiCaprio (approaching 30) was going from the heartthrob capturing the hearts of audiences to a capital A actor, and this role allows him to exhibit all of that. The performance is still propelled by his charm, but having to put on so many faces also allows him to show off his range. Sandwiched in between a pair of Martin Scorsese epics, this Steven Spielberg collaboration continued quite the run of heavyweight director pairings in a star-making period. In a cast full of big names, DiCaprio demands your attention with his magnetic screen presence as you’re taken in like many of his victims. (Jake Bourgeois)

Standing out among the loaded cast of The Departed requires a special performance, and Leonardo DiCaprio delivers exactly that as William Costigan Jr. The compelling story gives him plenty to work with as a young Bostonian trying to go straight and rise above a troubled family background, only to be forced right back into that world for undercover work. Nobody has ever sold the anxiety and angst of undercover life as well as DiCaprio. In scenes opposite Jack Nicholson’s mob boss Frank Costello, he must project confidence, and convey a subtle, hidden layer of nervous sweat from the fear of being caught. Opposite Vera Farmiga’s Dr. Madolyn Madden, he purges all the stress, fear and nerves with heart and emotional breakdowns. Opposite Martin Sheen’s Captain Queenan, he displays manic panic while grasping to complete the mission and earn his freedom. The duality of seeing Matt Damon’s Colin Sullivan embodying the other end of the spectrum only adds to the intrigue. This is arguably DiCaprio’s most diverse performance, and he steals the show amid an all-time great cast. (Jason Mack)

Leonardo DiCaprio’s career shift at the time of Django Unchained made big waves, as few expected him to show up as such a villainous character. He’s impressive and vile as Calvin Candie, the owner of the biggest and most brutal slave plantation in the land. Django is the tale of a free slave and a bounty hunter in search of this former slave’s wife, but this perilous road leads them right into Candieland. Candie is quite the despicable snake (or dragon, if you believe some good old-fashioned German mythology). DiCaprio sells this character as a spoiled, dense, ignorant, angry, and terrifying man-child. Candie might not seem like the sharpest tool in the shed, but when he realizes what is being done to him, he unleashes in a violent and angry way. You can tell that DiCaprio is eating up this performance, but that doesn’t mean it’s not horrifying, unnerving, and scary underneath all the flash and “gentlemanly” behavior. (Shane Conto)

Among a long roster of exceptional and memorable performances in Christopher Nolan’s films, Leonardo DiCaprio’s turn as Dom Cobb in Inception is often overlooked. Meanwhile, it’s my favorite of his performances. DiCaprio doesn’t make his performance the story of the movie, like in The Wolf of Wall Street or The Revenant — instead, he delivers a lot of what could be clunky expositional dialogue while maintaining a true emotional core. I wouldn’t care about any of the dream babble if it weren’t all hinging on Cobb getting back to his kids, and forgiving himself for his past failures. This is what differentiates Inception from Tenet for me — I deeply care about the character arcs in the former, while I’m left disappointingly cold by the latter, and it’s all made possible by a knockout performance by one of our finest living actors. (Robert Bouffard)

I never imagined I’d see Leonardo DiCaprio play as much of an utter fool as he does in Killers of the Flower Moon. Known for his charm and leading man gravitas, DiCaprio has rarely stepped into the shoes of an outright imbecile. As Ernest Burkhart, a real-life figure who returns from war only to fall under the sway of his uncle’s murderous scheme to steal Osage oil headrights, DiCaprio transforms into a character both diabolical and darkly comedic. He embodies an oaf who recognizes the evil in what he’s doing, but chooses compliance anyway. At times, you glimpse his internal conflict, but whenever he edges toward decency, it’s already far too late. The result is a character you can’t help but love to hate — weak, complicit, and unforgettable. DiCaprio may not be the film’s brightest star, but he anchors crucial moments with a performance that lingers long after the credits roll. (Chantal Ashford)

The one that finally won Leonardo DiCaprio his Oscar, his performance in The Revenant would be notable for that alone, if nothing else. In the role of Hugh Glass, a frontiersman who is set on the revenge path against those who left him for dead after a bear mauling, DiCaprio puts in perhaps the grittiest, grimiest performance of his career. It’s the type of performance that the Academy loves, as the work DiCaprio’s work comes through on screen, but that doesn’t diminish said work. Watching what Glass goes through in the Canadian wilderness is a huge component of why the audience is so invested in his quest for vengeance. And, for all the memes, that bear scene is truly terrifying. (Jake Bourgeois)

With a belly full of boyish charm and an optimistic future ahead of him that will never come to pass, Jack Dawson is endearing from the moment he first appears on screen, and that is in no small part due to Leonardo DiCaprio’s unfettered confidence. James Cameron’s Titanic catapulted Leo to his peak superstardom, and the character became almost instantly iconic due to his rugged look and memorable lines. From the moment he boards the doomed ship to (spoilers!) his last gasp above water, Jack makes quite the impression on many lives, including changing Rose (Kate Winslet) forever. Whether or not he could have also fit on the door with Rose continues to be debated to this day — come on, guys, he says in the movie that if he got on, they would both sink — but the tragedy of his demise endures as one of the saddest and most heartbreaking moments of ’90s cinema. (Rowan Wood)

Just 19 years old when his breakout performance in What’s Eating Gilbert Grape was released, Leonardo DiCaprio’s performance is one that would never happen today, given our modern sensitivity towards portrayals of characters with disabilities. Taking on the role of a boy with Autism runs a real risk of veering into Simple Jack from Tropic Thunder territory. Thankfully, DiCaprio’s performance feels so masterfully authentic that it not only allows the film to remain watchable to this day, but it also earned him his first Oscar nomination, launching the career of the next great Hollywood icon, following in the footsteps of stars like James Dean and River Phoenix before him. (Foster Harlfinger)

The quintessential movie for frat guys everywhere, for better or worse, The Wolf of Wall Street is a film whose craft is simply undeniable. Martin Scorsese was 71 years old when he directed the film in 2013, yet it has the energy of one directed by a younger man with something to prove, perhaps aided by a hefty dose of cocaine. At the film’s center is a manic powerhouse performance from Leonardo DiCaprio as the morally dubious Jordan Belfort. Across the film’s three-hour runtime, DiCaprio gets the chance to flex his range as an actor. Look no further than the sequence of Belfort crawling back into his car while high on Quaaludes to see what a gifted physical, dramatic, and comedic performer DiCaprio is. Were it not for Matthew McConaughey’s breakout year as a dramatic actor between True Detective, Interstellar, and Dallas Buyers Club, this could easily have been DiCaprio’s year to break his Oscar-less streak. (Foster Harlfinger)