Top 5 Leonardo DiCaprio Movies!

Arguably the most prolific and acclaimed actor of our time, Leonardo DiCaprio has provided a stacked filmography over his 30-plus-year career, one that has garnered him 6 Oscar nominations and one win for his acting. DiCaprio has worked with some of the most legendary directors in the modern landscape, featuring work with Christopher Nolan, Steven Spielberg, James Cameron, Alejandro G. Iñárritu, and, most notably, his 6 collaborations with Martin Scorsese. DiCaprio is back on the big screen, re-entering cinemas with One Battle After Another, headed by another prestigious director, Paul Thomas Anderson. With the new blockbuster receiving otherworldly praise and reviews, where does it fit in with the rest of Leo’s unmatched portfolio? Here are our top five movies in which Leonardo DiCaprio has graced the silver screen as the leading man!

1. The Departed (2006)

Starting off with a star-studded film, and one that pushes its way straight to the top of DiCaprio’s hit list, is Martin Scorcesse’s The Departed. In this crime thriller, we find DiCaprio as a double agent, a Boston cop working undercover within a gang led by the incomparable Jack Nicholson. Leo and Jack’s brilliant performances are complemented by equally outstanding jobs from Matt Damon, Vera Farmiga, Alec Baldwin, and Mark Wahlberg. The Departed won four Oscars on the big night, taking home the Best Picture win after nabbing Director, Adapted Screenplay, and Film Editing. Although we would not count this individually as DiCaprio's finest work, The Departed is a clear top choice for the best overall movie in his catalog. (Available on VOD/Digital)

2. One Battle After Another (2025)

Recency bias may be a true phenomenon, but with One Battle After Another, this sentiment can be thrown out the window -- or in this case, off the roof. Paul Thomas Anderson’s new epic of genre-blending madness has taken the cinematic community by storm in a matter of days, and rightfully so. DiCaprio is absolutely hilarious wiht his Lebowski-esque character Bob Ferguson, a former revolutionary whose foe of fifteen years, Sean Penn, has returned to eliminate him and his daughter, newcomer Chase Infiniti. Penn is a clear favorite amongst supporting actors to win the Oscar thus far into the year, giving a performance of the decade as Col. Steven J. Lockjaw, with other supporters, Regina Hall, Teyana Taylor, and Benicio Del Toro delivering on their ends as well. Go catch this masterpiece on the biggest screen you can to see one of the best DiCaprio movies we’ve seen! (In theatres now)

3. Once Upon a Time... in Hollywood (2019)

Featuring another comedic-infused execution of his role, DiCaprio takes on action star Rick Dalton in Quentin Tarantino’s Once Upon a Time... in Hollywood. Along with Brad Pitt as DiCaprio’s stunt double and Margot Robbie as the infamous Sharon Tate, we get a glimpse into the near future of stardom, with Margaret Qualley, Mikey Madison, Maya Hawke, Victoria Pedretti, and Sydney Sweeney all making appearances before their breakouts. Tarantino’s look into the waning end of the golden age of Hollywood in 1969 also features glimpses of cultural change into the '70s as well as the Manson murders, with DiCaprio and company bringing this era to life with the director’s signature violent and suspenseful touch. Once Upon a Time... in Hollywood also performed well at the 2020 Academy Award ceremony, with DiCaprio earning a nod, and Pitt taking one home for his supporting role that is soon seeing a spin-off led by David Fincher. (Available on VOD/Digital)

4. Inception (2010)

As mentioned, DiCaprio has worked with tons of auteurs in his time, and with Inception, he teams up with Christopher Nolan to deliver a movie that is a bit esoteric amongst his other projects. In Inception, Leo leads another big-time ensemble as a dream-jumping, conscious-entering thief. Inspired by Satoshi Kon’s Paprika, this sci-fi heist film takes the genre to the next level, with an incredible Hans Zimmer score and absolutely stunning set pieces. Along with Cillian Murphy, Tom Hardy, Joseph Gordon-Levitt, and Elliot Page, DiCaprio’s sole Nolan collaboration (thus far) proves to be one of the best in either of their filmographies. (Stream on HBO Max)

5. The Wolf of Wall Street (2013)

Back with his old pal Martin Scorcesse, DiCaprio ignited audiences with his borderline-perfect portrayal of the infamous Wall Street figure Jordan Belfort. The Wolf of Wall Street has gleaned a stigma through its popularity amongst young men, one that has undeservingly tarnished its image over the years. In fact, due to its reputation, we would consider Scorsese to be incredibly underrated, as DiCaprio’s work in this film could arguably be his greatest. Leo finds himself once again surrounded by incredible co-stars, with Jonah Hill giving a fun follow-up showing to his inaugural dramatic role in Moneyball, and Margot Robbie breaking into her Hollywood stardom. (Available on VOD/Digital)

Honorable Mentions: Titanic, Catch Me If You Can, Shutter Island, The Aviator