10’What’s Eating Gilbert Grape' (1993)
Directed by Lasse Hallström
What’s Eating Gilbert Grapefollows the titular Gilbert Grape (Johnny Depp), a young man burdened with the responsibilities of caring for his dysfunctional family in a small boring town. Gilbert juggles his dead-end job at a grocery store, the weight of looking after his obese mother (Darlene Cates), and his mentally challenged younger brother Arnie (Leonardo DiCaprio), whose unpredictable behavior keeps everyone on edge.
DiCaprio’s portrayal of Arnie is an astonishing display of his talents from early in his career. At just 19 years old, he delivered a raw and authentic performance that earned himhis first Oscar nomination for Best Supporting Actor. His sensitive depiction of Arnie is filled with nuance and sincerity, bringing a humanity that avoids caricature. UnderLasse Hallström’s understated direction,What’s Eating Gilbert Grapedelicately balances moments of heartbreak and humor, becoming a deeply emotional portrait of family dynamics. This film cemented DiCaprio as a talent to watch, and his performance remainsone of the most memorable in his illustrious career.
What’s Eating Gilbert Grape
9’Romeo + Juliet' (1996)
Directed by Baz Luhrmann
Baz Luhrmann’sRomeo + Julietis a dazzling modern reimagining of the Shakespeare classic, set in Verona Beach. With the original Shakespearean dialogue intact, the film follows the iconic star-crossed lovers, Romeo Montague (DiCaprio) and Juliet Capulet (Claire Danes), as they fall in love with each other despite their families' disdain for one another. Audiences may know what happened at the climax of the story, but Luhrmann updates the story with striking visuals and an iconic soundtrack.
DiCaprio’s performance as Romeo captures the fiery passion of the character, making him an ideal romantic lead for this modernized adaptation. Despitereports of a feud, his chemistry with Claire Danes is electric, even with the original dialogue which flowed naturally in the modern setting. Luhrmann’s bold directorial visionbrings Shakespeare’s story to lifein a way that is accessible and engaging, especially for younger audiences, without sacrificing the depth of the original material. DiCaprio collaborated again with Luhrmann for another modern take on the classic novel,The Great Gatsby.
Romeo + Juliet
Directed by Sam Mendes
Sam Mendes’Revolutionary Roadfollows Frank and April Wheeler, a seemingly perfect couple grappling with dissatisfaction and unfulfilled dreams. As their shared vision of an ideal life in Paris begins to crumble under the weight of societal pressures and personal insecurities, their relationship descends into heartbreak and despair. Based onRichard Yates’ acclaimed novel, the film reunited Leonardo DiCaprio andKate Winsletfor the first time sinceTitanic.
DiCaprio delivers an understated, nuanced performance as Frank. He perfectly captured the character’s charm, insecurity, and inner turmoil. Winslet matches him with equal intensity, portraying April’s longing for freedom with vulnerability. This film is a perfect reunion that shows growth for both actors. While it didn’t earn the same level ofcommercial success as other DiCaprio films,Revolutionary Roadis an essential piece of his filmography, showcasing his talent for diving deep into complex, emotionally fraught roles. His stellar performance in this film isone of his underrated roles to date.
Revolutionary Road
7’Inception' (2010)
Directed by Christopher Nolan
InInception,Leonardo DiCaprio stars as Dom Cobb, a skilled thief specializing in extracting secrets from within the subconscious during the dream state. When offered a chance to erase his criminal record and reunite with his family, Cobb accepts an ambitious job—performing “inception,” planting an idea in someone’s mind instead of stealing one. Cobb assembles a team to enter the dream of a business heir, but as the layers of dreams deepen, his own subconscious threatens to unravel the mission.
Christopher Nolan’s ambitiouscerebral blockbusterneeded a leading actor with DiCaprio’s talents to anchor the film and make it believable, and he nailed this performance perfectly. DiCaprio brings intensity and vulnerability that’s needed for the character, while leading the star-studded ensemble with grace. Without his performance, audiences probably would not be discussingthe film’s memorable endinguntil today.Inceptionwas a critical and commercial triumph, grossing over $800 million worldwide and earning four Academy Awards. The film is DiCaprio’s second-biggest hit, just behind a certain billion-dollar epic film.
6’The Revenant' (2015)
Directed by Alejandro G. Iñárritu
Set in the brutal wilderness of the early 19th century,Alejandro G. Iñárritu’sThe Revenanttells the story of Hugh Glass (DiCaprio), a frontiersman who is left for dead after being savagely mauled by a bear and betrayed by his fellow expedition member, John Fitzgerald (Tom Hardy). Fueled byan unrelenting will to surviveand a thirst for justice, Glass endures unimaginable physical and emotional trials to exact his revenge.
DiCaprio’s portrayal of Glass earned him his long-awaited first Academy Award for Best Actor. His performance displayed his physical acting ability, with intense, raw emotions and minimal dialogue. The bear attack sequence is a harrowing sequence and isthe film’s most memorable moment. Iñárritu’s meticulous direction, combined withEmmanuel Lubezki’s use of natural light, creates an immersive experience that feels haunting and poetic. The film’s 12 Academy Award nominations and its success at the box office underscore its status as a must-see film, as well as a career-defining moment for DiCaprio.
The Revenant
5’Titanic' (1997)
Directed by James Cameron
James Cameron’sTitanicis an epic romance that follows the ill-fated love story of two people from different worlds, Jack Dawson (Leonardo DiCaprio) and Rose DeWitt Bukater (Kate Winslet). Meeting aboard the Titanic during its doomed maiden voyage, the pair striked an unlikely romance despite their differences. The situation grows more complicated as Rose is set to marry the rich Cal Hockley (Billy Zane). As the Titanic collides with an iceberg, their fateful love is put to the ultimate test.
With breathtaking visuals and an emotional story, Cameron delivers a cinematic masterpiece that balances historical grandeur with intimate storytelling, whichinspired a lot of copycats. DiCaprio’s unforgettable portrayal of Jack catapulted his status to global stardom and his chemistry with Winslet turned the film into a cultural phenomenon.Titanicearned a monumental achievement in filmmaking, with 11 Academy Awards, including Best Picture anda staggering $2.2 billion dollars worth of tickets. The film’s sweeping scope, historical detail, andtimeless love story, depicted by DiCaprio and Winslet, put the film in many audiences' hearts to this day.
4’Catch Me If You Can' (2002)
Directed by Steven Spielberg
Directed bySteven Spielberg,Catch Me If You Canis based on the true story of Frank Abagnale Jr. (Leonardo DiCaprio), a teenage con artist who became one of the most successful fraudsters in U.S. history. Frank forges millions of dollars in checks while posing as a pilot, a doctor, and even a lawyer, using his charm and intelligence to stay one step ahead of the authorities. FBI agent Carl Hanratty (Tom Hanks) is tasked to capture him, leading him on a cat-and-mouse chase across the globe.
Catch Me If You Canisone of Spielberg’s finest films. The lead performances from DiCaprio and Tom Hanks are irresistible. DiCaprio’s ability to effortlesslytransition between deception and sinceritygives the character depth, making Frank both likable and tragic. Paired with Hanks’ grounded performance, the two actors create a compelling dynamic that makes the story exciting to follow. Witha livelyJohn Williamsscorethat adds an extra layer of charm, the film is not only a critically-acclaimed caper, but also an entertaining film beloved by audiences.
Catch Me If You Can
3’The Departed' (2006)
Directed by Martin Scorsese
A remake of an acclaimed Hong Kong crime dramaInfernal Affairs,The Departedtransported the story to Boston’s underworld, following two men on opposite sides of the law: Billy Costigan (DiCaprio), an undercover cop infiltrating the Irish mob led by Frank Costello (Jack Nicholson), and Colin Sullivan (Matt Damon), a mob mole embedded in the Massachusetts State Police. Directed byMartin Scorsese, the film also starsMark Wahlberg,Vera FarmigaandMartin Sheen.
Inhis third collaboration with Scorsese, DiCaprio captures the desperation of a man trapped between his duty and the weight of his double life. The film’s star-studded cast, including Nicholson, Damon, and Wahlberg, complements his performance, creatinga layered and dynamic ensemble. Due to a peculiar Oscar rule, DiCaprio was not nominated for Best Actor as he was already nominated forBlood Diamond, despite getting double nominations in the same category at the Screen Actors' Guild and the Golden Globes. Nevertheless,the gripping gangster thrillerearned Scorsese his long-awaited Oscar for Best Director and also took home the Best Picture trophy.
The Departed
2’Django Unchained' (2012)
Directed by Quentin Tarantino
Quentin Tarantino’s irreverent WesternDjango Unchainedfollows Django (Jamie Foxx), a freed slave who teams up with German bounty hunter Dr. King Schultz (Christoph Waltz) to rescue his wife, Broomhilda (Kerry Washington), from the cruel plantation owner Calvin Candie (Leonardo DiCaprio). As Django learns the art of bounty hunting from Schultz, their journey brings them face-to-face with the horrors of slavery and the brutality of Candie’s estate.
Calvin Candie marks the rare occasion whereDiCaprio plays the antagonist. DiCaprio masterfully conveys the character’s charm, cruelty, and decadence, making Candie one of the most unsettlingvillains in Tarantino’s universe. The director’s signature long scene enabled DiCaprio to play freely alongside Foxx, Waltz andTarantino’s frequent collaboratorSamuel L. Jackson, leading to the infamous incident where he kept on acting despite injuring his hand. While DiCaprio didn’t score a nomination for this film, his next work with Tarantino inOnce Upon A Time in Hollywood, earned him a nod.
Django Unchained
1’The Wolf of Wall Street' (2013)
The Wolf of Wall Streetchroniclesthe rise and fall ofJordan Belfort(DiCaprio), a stockbroker who achieves staggering wealth through fraudulent schemes on Wall Street. Based on Belfort’s memoir, the film follows his transformation from a hungry, ambitious young trader to a hedonistic tycoon addicted to power, drugs, and excess. As Belfort amasses fortune and influence, the authorities start to close in, leading him closer to his eventual downfall.
DiCaprio delivers one of the most dynamic performances of his career, displaying his charisma to embody Belfort’s charm and also his physical acting. Working once again with Scorsese, DiCaprio is able to simultaneously make the charactermagnetic and detestable. His interactions with the ensemble that includesJonah HillandMargot Robbieelevate the film further, adding depth and humor to the debauchery. Thiscontroversial, high-octane,no-holds-barred masterpieceremains a cornerstone in modern cinema and an essential showcase of DiCaprio’s unmatched talent.
