Leonardo DiCaprio’s 18 Best Movie Performances: From ‘Once Upon a Time in Hollywood’ to ‘Killers of the Flower Moon

Role: Jim Carroll

Distributed by: New Line Cinema
Directed by: Scott Kalvert
Written by: Bryan Goluboff

The scene that proves it: “Mom, can you give me some money please?”

As a drug-addicted high school basketball player, DiCaprio displays the underlying fury of a troubled youth. Playing well off his co-stars, particularly Mark Wahlberg as his friend Mickey, and Lorraine Bracco, as his heartbreaking mother, he’s able to navigate some of the film’s obvious pitfalls.

Role: Howard Hughes

Distributed by: Warner Bros
Directed by: Martin Scorsese
Written by: John Logan (based on “Howard Hughes: The Secret Life” by Charles Higham)

The scene that proves it: “Come in with the milk.”

Playing billionaire Howard Hughes was well within Leonardo DiCaprio’s range as an actor, even though the audience has to work a bit too hard to accept him as a 40-year-old (he was in his late 20s at the time of filming). So instead, he re-teams with the master director Martin Scorsese, who previously worked on “Gangs of New York” (2002) for the epic. Together, the two who set out to depict the life of the aviation pioneer over 20 years as his obsessive-compulsive disorder becomes increasingly evident, it’s the role that put him on the Oscar map, garnering his first lead actor nomination, with the film leading the way with 13, including the first of his many surprise supporting actor noms for Alan Alda.

Role: Dom Cobb

Distributed by: Warner Bros.
Directed by: Christopher Nolan
Written by: Christopher Nolan

The scene that proves it: “James and Phillipa”

Under the thumb of a box office juggernaut, DiCaprio slides through the Christopher Nolan entry, giving it weight and emotion when not showcasing tumbling rooms and white vans. Helped greatly by Marion Cotillard (an awards-worthy performance), this was also his third role in the string of what the internet called the “dead wives club” (following “Revolutionary Road” and “Shutter Island”).

Role: Jack Dawson

Distributed by: Paramount Pictures/20th Century Fox (now 20th Century Studios)
Directed by: James Cameron
Written by: James Cameron

The scene that proves it: First class dinner.

The role that made him a superstar. “Titanic” is the highest-grossing film of all time (in 1997) and the second film to win 11 Oscars, including best picture. Unfortunately, his charm and obvious good looks didn’t impress the Academy enough to include him in the best actor lineup. Still, he would eventually get his due more than 20 years later.

Role: Danny Archer

Distributed by: Warner Bros
Directed by: Edward Zwick
Written by: Charles Leavitt

The scene that proves it: “This is Africa.”

Leo gets to sport an impressive accent, which at the time started drawing comparisons to Meryl Streep, in Edward Zwick’s action-thriller. While the script has its flaws, DiCaprio, alongside the incredible, Oscar-nominated Djimon Hounsou, is able to elevate the film considerably.

Role: Calvin Candie

Distributed by: The Weinstein Company/Sony Pictures
Directed by: Quentin Tarantino
Written by: Quentin Tarantino

The scene that proves it: The Dinner Table

One of DiCaprio’s most audacious roles, his first outing with Quentin Tarantino had him playing a suave and terrifyingly villainous role. Depending on who you ask, DiCaprio’s snub from the Academy was due to category fraud, because his co-star and eventual winner Christoph Waltz was campaigned in supporting, rather than lead.

Role: Edward “Teddy” Daniels / Andrew Laeddis

Distributed by: Paramount Pictures
Directed by: Martin Scorsese
Written by:  Laeta Kalogridis

The scene that proves it: “Live as a monster or die as a good man”

Teddy Daniels is a complex man, and DiCaprio rides multiple waves of inquisition and emotion in Martin Scorsese’s underrated thriller. Likely due to an early February release, the film went unnoticed in categories like production design and sound mixing, but none were as egregious as DiCaprio’s overlooked work, demonstrating masterclass sparring with co-stars Ben Kingsley and Michelle Williams. It comes together splendidly with his question to Mark Ruffalo’s Chuck following the film’s big reveal: “Do you live as a monster or die as a good man?”

Role: Dr. Randall Mindy

Distributed by: Netflix
Directed by: Adam McKay
Written by: Adam McKay, David Sirota

The scene that proves it: “What have we done to ourselves?”

Leonardo DiCaprio takes on a subject dear to his heart (climate crisis) but executes it in a way we haven’t seen of him in any other roles. As Dr. Randall Mindy, an astronomer who, along with his colleague Kate Dibiasky (played courageously by Jennifer Lawrence), try desperately to inform the world of its impending doom, he gets to stretch out in both his dramatic and comedic moments. His chemistry with Brie Evantee (played expertly by Cate Blanchett) is one of the film’s brighter spots, in an otherwise very bleak look at where our species will inevitably end up (unless things begin to change).

Role: Frank Wheeler

Distributed by: DreamWorks Pictures
Directed by: Sam Mendes
Written by: Justin Haythe

The scene that proves it: “Shell of a woman”

We saw a glimpse of what Jack and Rose would have been like if they shared the floating door in Sam Mendes’ tragic and genuinely moving portrait of a marriage in 1950s suburbia. DiCaprio’s Frank Wheeler doesn’t ask for the viewer’s sympathy, rather than just allowing us to wrestle with our own feelings as he cheats, whines and runs through the movie. Anchored by Kate Winslet’s career-best performance, both were snubbed by the Academy (Winslet was nominated and won instead for “The Reader”). Sometimes the movies are just too real to embrace.

Role: Arnold “Arnie” Grape

Distributed by: Paramount Pictures
Directed by: Lasse Hallström
Written by: Peter Hedges

The scene that proves it: “Dad’s dead.”

The only performance of DiCaprio’s career that resulted in an Oscar nomination for best supporting actor (arguably one of the best lineups in Academy history), his intellectually disabled Arnie Grape in Lasse Hallström’s poignant gem is one that could have easily aged poorly with hindsight but has not. Commanding the scenes opposite Johnny Depp and an outstanding Darlene Cates (who should have been nominated herself), his sensitive and sentimental hits all the right notes.

Role: Frank Abagnale

Distributed by: DreamWorks Pictures
Directed by: Steven Spielberg
Written by:  Jeff Nathanson

The scene that proves it: Getting caught in France

As Leo’s babyface seemed to be a hindrance in the late ’90s and early 2000s, at least in terms of being taken seriously as a leading man, his Frank Abagnale Jr. in Steven Spielberg’s “Catch Me If You Can” was one of the first examples that our “Growing Pains” orphan was growing up and had something substantial to offer the acting world. Opposite Tom Hanks and Christopher Walken, his 21-year-old conman on the run plays out perfectly, especially in his capture-in-France scene, where he really unloads his arsenal. Unfortunately, only the Golden Globes nominated him in best actor in a drama.

Role: Tobias Wolff

Distributed by: Warner Bros.
Directed by: Michael Caton-Jones
Written by: Robert Getchell

The scene that proves it: “Is it empty?”

If there is a film, and performance of Leonardo DiCaprio’s career that could be considered the most underrated, Michael Caton-Jones’ “This Boy’s Life” truly hits the mark. As Tobias Wolff, DiCaprio navigates teenage years, in the shadow of abuse and a yearning to find his way in the world. Not just discounted for DiCaprio, it boasts an amazing turn from Robert DeNiro, and a criminally ignored Ellen Barkin, who with her young co-star, should have been given more of an Academy shake. The same year as his nominated “What’s Eating Gilbert Grape,” the Oscars were not ready to double nominate a 21-year-old actor in favor of winner Tom Hanks, along with Daniel Day-Lewis, Laurence Fishburne, Anthony Hopkins and Liam Neeson.

Role: Hugh Glass

Distributed by: 20th Century Fox (now 20th Century Studios)
Directed by: Alejandro G. Iñárritu
Written by:  Mark L. Smith, Alejandro G. Iñárritu

The scene that proves it: Bear attack.

The visceral and harshly engaging look at Hugh Glass’ journey following a bear attack is one of DiCaprio’s most daring. Raw and brutal, his physical interpretation of revenge is just as impressive as his emotional take, partnered beautifully with Tom Hardy’s nominated performance. Along with director Alejandro G. Iñárritu’s and cinematographer Emmanuel Lubezki’s, the long-overdue Oscar statuette came his way. In that field of nominees, it was well deserved, especially after climbing into a dead carcass.

Role: Romeo

Distributed by: 20th Century Fox (now 20th Century Studios)
Directed by: Baz Luhrmann
Written by:  Craig Pearce, Laz Luhrmann

The scene that proves it: Love at first sight.

Baz Luhrmann’s “William Shakespeare’s Romeo + Juliet,” the modern take on the classic play, is one of the most underrated and invigorating films of the 1990s. DiCaprio’s lovestruck Romeo manages to light up the screen at every turn, showcasing one of the most explosive of his acting career. Likely seen at the time, and still too often today, as a teenage YA drama, Oscar showed no interest in shortlisting his performance (although the art direction nomination is clutch). His chemistry with Claire Danes, who also should have been given more love (thank you MTV Movie Awards for noticing), is sensational. Thanks to the pair, the song “Kissing You” by Des’ree is engraved in my mind for all time. All I need is a two-sided aquarium and I’m going to start my reenactments.

DiCaprio has partnered many times with filmmaking icon Martin Scorsese, but his comedic take on Jordan Belfort’s time of wealth, corruption and drug use is one of the actors’ most jaw-dropping. At a hearty three-hour runtime, his all-staff monologues, physical liquefying to Margot Robbie’s “no more panties” speech, and a hilarious attempt to crawl to his car after a late reaction to quaaludes is just the chef’s kiss of his career thus far. He found his way to an Oscar nomination, despite the film being released just under the gun and missing the crucial SAG awards deadline. That resulted in him on the sidelines in favor of Matthew McConaughey’s work in “Dallas Buyers Club.”

Role: Billy Costigan

Distributed by: Warner Bros.
Directed by: Martin Scorsese
Written by: William Monahan

The scene that proves it: “Two pills?”

In 2006, DiCaprio delivered a one-two punch powerhouse duo with his nominated work in Edward Zwick’s “Blood Diamond” and Martin Scorsese’s best picture winner, “The Departed.” Double nominated at the Golden Globes and nominated in best supporting actor at the SAG Awards; all this contributed to his snub. Add in campaign confusion and a rule that doesn’t allow an actor to be double nominated in the same category. His undercover Billy Costigan couldn’t find a consistent awards message.  Makes you wonder, if he was nominated for Scorsese’s film, could he have been a formidable challenger to Forest Whitaker (“The Last King of Scotland”)? If you’re one of the few that sees the crime drama as an ensemble, he could have also challenged winner Alan Arkin (“Little Miss Sunshine”), who upset Eddie Murphy (“Dreamgirls”).

Role: Ernest Burkhart

Distributed by: Apple Original Films/Paramount Pictures
Directed by: Martin Scorsese
Written by: Eric Roth, Martin Scorsese (based on “Killers of the Flower Moon” by David Grann)

The scene that proves it: “Insulin.”

DiCaprio has never played a character so vile and grotesque as seen in his Ernest Burkhart, the husband of an Indigenous woman who contributes to the murdering of dozens of natives from the Osage tribe community.

While on the surface, DiCaprio plays up the “buffoonery” of the man as he lacks the intelligence to be truly cunning, he also conveys the torment and guilt that we can hope the real-life man began to feel at some point during his horrific acts. It’s one of his most surprising outings as an actor, and hopefully, those like this will be explored further throughout his career.

“Killers” premiered at the Cannes Film Festival, receiving acclaim from critics and attendees.

Role: Rick Dalton

Distributed by: Sony Pictures
Directed by: Quentin Tarantino
Written by:  Quentin Tarantino

The scene that proves it: Rick forgetting his lines.

Call it the perfect marriage of an actor feeling like he’s at the crossroads of his career, or the fact that he’s just so infectiously funny and charming but his Rick Dalton in Quentin Tarantino’s look at classic Los Angeles is his best work yet. Maybe it’s chemistry alongside Oscar-winning co-star Brad Pitt, but it can be argued that if he had not won for “The Revenant” in 2016, he would have undoubtedly unseated Joaquin Phoenix’s monstrous turn in “Joker.” He’s never made a flamethrower so cool.