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Top 5 Leonardo DiCaprio Movies

Taking advantage of a good script and a talented director, DiCaprio stripped away his heartthrob image to deliver this gripping tale of revenge and morality. A still baby-faced DiCaprio proved he could master Shakespearian dialogue in Baz Luhrmann’s extravagant update of the classic romantic tragedy. It was a pivotal moment in his career, as he moved away from heartthrob roles and toward a legitimate elite actor.

1. The Wolf of Wall Street

After winning rave reviews for his performance as a cocky cowboy in the non-traditional spaghetti western, Leo continued to impress with this dark tale of obsessive celebrity. It wasn’t a commercial success, but it proved that he had the chops to stand up against big-name directors and actors.

While the movie didn’t rank among the best of his career, it was a critical success and marked the beginning of his brooding bad-love period. DiCaprio was nominated for an Oscar for his work here, and he delivered a fine lead performance.

Martin Scorsese’s adaptation of Dennis Lehane’s psychological thriller finds Leo in fine form as a U.S. Marshal tasked with hunting down a dangerous terrorist suspect in a region riddled with conflict. It’s an underrated entry in this director’s canon and an excellent early showcase for one of Hollywood’s most dedicated young stars.

2. The Departed

After Titanic, DiCaprio retreated into brooding bad-love movies and cultivated an intense relationship with Martin Scorsese. The Departed marks a crucial transitional moment, as Leo begins to leave behind his pretty boy persona and become a true elite actor.

This gripping cops-and-robbers thriller is a remake of Hong Kong’s Infernal Affairs and stars DiCaprio as a rookie cop trying to infiltrate the mob (with the help of a gangster played by Matt Damon). He delivers one of his most internalized performances, stressing the dangers and moral compromises of a job where you could be made or killed at any time.

A late-period Baz Luhrmann classic, this updating of Shakespeare’s timeless tragedy is a delicate and romantic tragedy with a tumultuous finale. It’s the perfect early showcase for DiCaprio’s ability to convey giddy infatuation and irrepressible sexual urges.

3. The Wolf of the Nile

A decade after Baz Luhrmann’s modernization of Romeo and Juliet turned DiCaprio into a teen heartthrob, the actor proved he had much more to him with this tough coming-of-age drama. This underrated primewire film showcases DiCaprio as an ambitious young man who isn’t afraid to go against the grain.

The sequel to Gangs of New York proves that Scorsese and DiCaprio make an excellent pair. In this powerful biopic, Leo plays aviation pioneer Howard Hughes, who tries to keep his OCD and impulsiveness at bay by constantly inventing new dreams.

This gorgeously filmed survival adventure is hard to stomach, but the stunning scenery and a riveting performance from DiCaprio help to make it worth seeing. It was the perfect showcase for Leo to prove he had more to offer than his poster-boy looks. He was a feral presence in this movie.

4. The Great Gatsby

Leonardo DiCaprio reaffirmed his status as a global movie star with this adaptation of F. Scott Fitzgerald’s classic novel. He reunited with director Baz Luhrmann, who he worked with on Romeo + Juliet, in this flashy take on the story of star-crossed lovers.

The Great Gatsby, which takes place during the Jazz Age (a term Fitzgerald popularized) or the Roaring Twenties, depicts its historical moment with precision: the postwar economic expansion of America, the emergence of jazz music, and the abundance of illicit alcoholic beverages. Fitzgerald later described the period in an essay as “an entire race deciding on pleasure and hedonism.” The ostentatious extravagance of West Egg’s culture is a reflection of the unprecedented prosperity that emerged during Prohibition, a period rife with illicit enterprises involving the illicit trade of alcoholic beverages.

In this gripping mob drama, Leo’s spineless character is a model of passive wickedness, and his performance earned him the Oscar for Best Actor. The film also boasts a top-notch cast, including Robert De Niro and Matt Damon.

5. Inception

One of DiCaprio’s most mind-bending films, this Christopher Nolan collaboration showcases the actor in top form. Easily his best on screen performance, he proves he can do more than just swoon over beautiful women.

Leo plays Jordan Belfort in this cautionary tale of excess and corruption. His character’s rise and fall are the perfect vehicle for showing off his acting talents.

In a career that has seen him stray from the teeny-bopper romantic comedies of his early days, DiCaprio grew up on screen in Revolutionary Road. He continued to focus on choosing projects that matched his interests, like Alejandro G. Inarritu’s beautifully-filmed survival drama. During this period, he also took on the roles that would cement his status as a swoon worthy leading man, such as Titanic and The Revenant. He also began to choose directors that he believed in, including the likes of Martin Scorsese and Quentin Tarantino.

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