After hitting superstardom in the prior decade, Leonardo DiCaprio truly established himself as a juggernaut in the industry during the 2000s. He was one of the hottest rising stars that Hollywood had to offer coming into the decade thanks to his 1990s roles in movies like Titanic (1997) and Shakespeare in Love (1998), and the films on this list established him as a household name.
A couple of these titles stand out as being far lesser known than the others, but for the most part, the films on this list are the most recognizable of DiCaprio’s career. He also made lasting connections with directors like Martic Scorsese that would continue in 2023 with releases like Killers of the Flower Moon.
Updated on October 20th, 2023, by Rachel Johnson: This article has been updated with additional content to keep the discussion fresh and relevant with even more information and new entries.
9 The Beach
The first two entries on this list are among the least-known films of Leonardo DiCaprio’s entire career, let alone of the decade at hand. And that’s not without good reason. With The Beach (2000), director Danny Boyle failed miserably to recreate the critical success of his prior works — Shallow Grave (1994) and Trainspotting (1996), most notably.
The plot herein explores rather shallow waters, never venturing further into the ocean than it needs to in order to utilize DiCaprio’s name value, scoring big at the worldwide box office. It nearly tripled its $50 million budget despite qualitative shortcomings across the board of filmmaking tactics. But not even its financial success can land it higher than number nine on this list.
Stream on Starz
8 Don’s Plum
After this entry of the list, you’ll undoubtedly start to recognize the titles herein. This is far from the worst movie that Leonardo starred in throughout the 2000s, though. There’s a fairly large valley of quality separating Don’s Plum (2001) from the prior entry on the list. It’s just that the rough development process here in tandem with black-and-white, independent techniques of cinematography rendered it a failure with audiences.
But critics had mostly positive things to say, as the titular restaurant hosts a meaningful plot of four friends experiencing something of a falling out. In the end, too many viewers were left in the dark regarding Don’s Plum.
7 Body of Lies
Body of Lies
- Release Date
- October 10, 2008
- Director
- Ridley Scott
- Cast
- Leonardo DiCaprio, Russell Crowe, Mark Strong, Golshifteh Farahani, Oscar Isaac, Ali Suliman
- Rating
- R
- Genres
- Action, Documentary, Drama, Thriller
This particular crime film had far more potential than it eventually achieved. Along with DiCaprio, other names featured within this project include Russell Crowe in the costarring role, and Ridley Scott as the director. Those are two absolutely massive names in the industry for their respective crafts, but for some reason, everyone seemed to come up just short here with Body of Lies (2008).
Of course, it’s not the worst film you’ll read about today. The performances weren’t half bad, and it features its fair share of other quality filmmaking elements at play, like well-written dialogue and interesting practices of continuity editing. But in the end, it came up just qualitatively short of reaching this list’s upper echelon, coming in at number seven.
Stream on Max
6 Blood Diamond
Blood Diamond
- Release Date
- January 26, 2006
- Director
- Edward Zwick
- Cast
- Leonardo DiCaprio, Djimon Hounsou, Jennifer Connelly, Kagiso Kuypers, Arnold Vosloo, Antony Coleman
- Rating
- R
- Genres
- Adventure, Action, Documentary, Drama, Thriller
Taking place during the 1991–2002 Sierra Leonne Civil War, it’s worth noting off the bat that the title Blood Diamond (2006) refers to stones that are sold to finance conflicts after being mined from within war zones. But the war at hand is being fought between government loyalists and insurgent forces — and although this plot didn’t facilitate the greatest project from anyone involved, this Edward Zwick war thriller is almost worth your time for the performances alone.
Leo picked up an Academy Award nomination for Best Actor thanks to his efforts herein as Daniel “Danny” Archer, while his costar Djimon Hounsou was nominated for Best Supporting Actor as Solomon Vandy. The two share a dynamic rapport that carries the quality of the film at hand on its back. But Blood Diamond does have a few other qualitative filmmaking elements worth writing home about — the editing and sound design, for example. In the end, some fans would argue for a higher placement on the list, but the number six slot is admirable, nonetheless.
Rent on Apple TV+
5 Gangs of New York
gangs of new york
- Release Date
- December 14, 2002
- Director
- Martin Scorsese
- Cast
- Leonardo DiCaprio, daniel day-lewis, Cameron Diaz, Jim Broadbent, John C. Reilly, Henry Thomas
- Rating
- R
- Genres
- Crime, Documentary, Drama, History
In his first of many collaborations with American director Martin Scorsese, the actor at hand appeared here in Gangs of New York (2002) alongside Daniel Day-Lewis. The latter was without a doubt the film’s biggest takeaway as Bill “The Butcher” Cutting, even garnering a Best Actor nomination at the Academy Awards. But there are plenty of other performers worth writing home about herein, such as Cameron Diaz and John C. Reilly.
It chronicles DiCaprio’s character Amsterdam Vallon as he’s released from prison and initiates a revenge quest on the man who killed his father. The aforementioned Butcher, Day-Lewis’s role as an anti-immigrant gang leader led Gangs of New York to its qualitative peak, ultimately landing the film here at number five. Many fans might dispute this placement and argue for a higher spot, but that should only speak to the caliber of the rest of the list.
Stream on Max
4 Revolutionary Road
Revolutionary Road
- Release Date
- December 19, 2008
- Director
- Sam Mendes
- Cast
- Leonardo DiCaprio, Kate Winslet, Michael Shannon, Ryan Simpkins, Ty Simpkins, Kathy Bates
- Rating
- R
- Genres
- Drama, Documentary, Romance
Directed by Sam Mendes, this project features Leo alongside Kate Winslet as a married couple, Frank and April Wheeler, who are going through intense difficulties on multiple levels of their relationship. And along with those two performers, Revolutionary Road (2008) also features Kathy Bates — all three of whom appeared with one another in Titanic (1997), directed by James Cameron.
But the list of impressive performances by no means ends there. Kathryn Hahn, David Harbour, and Michael Shannon all perform valiantly herein. In fact, the last of those three even picked up a nomination for Best Supporting Actor at the Academy Awards. But in the end, Revolutionary Road reaches the upper echelon of the list thanks to the tangible chemistry of the primary characters.
Stream on Max
3 The Aviator
The Aviator
- Release Date
- December 17, 2004
- Director
- Martin Scorsese
- Cast
- Leonardo DiCaprio, Cate Blanchett, Kate Beckinsale, John C. Reilly, Alec Baldwin, Alan Alda
- Rating
- PG-13
- Genres
- Biography, Documentary, Drama
Directed by Martin Scorsese, the actor of the hour stars here in The Aviator (2004) as the real-life, titular character Howard Hughes. This is among the more impressive efforts of his career, to be frank. And although the overall product can’t quite be called the best Leo DiCaprio film of the 2000s, the number three spot is nothing to hang one’s head about.
It of course follows Hughes as he pioneers the aviation industry while in tandem creating the pre-Code, independent war film Hell’s Angels (1930). DiCaprio was easily the film’s biggest takeaway, as his depiction of Hughes’s struggle as a person with OCD spectrum disorder hit home on various level of emotion. But The Aviator also features the likes of Cate Blanchett (who plays the famous Katharine Hepburn, the real-life girlfriend of Hughes) along with John C. Reilly, Gwen Stefani, Jude Law, and several notable others. They all performed brilliantly, too.
Stream on Paramount+
2 Catch Me If You Can
Catch Me If You Can
- Release Date
- December 25, 2002
- Director
- Steven Spielberg
- Cast
- Leonardo DiCaprio, Tom Hanks, Christopher Walken, Martin Sheen, Nathalie Baye, Amy Adams
- Rating
- PG-13
- Genres
- Biography, Crime, Documentary, Drama
As far as Leonardo DiCaprio’s performances are concerned, especially from a modern perspective after his long run of hits in the 2010s, there’s an argument that his performance here in Catch Me If You Can (2002) doesn’t quite receive the love it deserves. He portrays tremendous charisma as the lead character Frank Abagnale Jr., a young con artist who would throughout the course of the film pose as a Pan American World Airways pilot, a parish prosecutor from Louisiana, and a doctor from Georgia.
The real-life story on which this film is based provided great entertainment as far as general pacing and plot points are concerned. But what’s perhaps most notable about Catch Me If You Can is the tremendous rapport that Leo shared with his coworker in Tom Hanks. The latter portrayed Carl Hanratty — who’s in turn based on Joseph Shea — an FBI agent tasked with tracking down Abagnale. There are several other notable performers herein, too. But it’s best you experience their efforts from a fresh perspective, as the quality of Catch Me If You Can lands it here in the penultimate spot.
Stream on Netflix & Paramount+
1 The Departed
The Departed
- Release Date
- October 5, 2006
- Director
- Martin Scorsese
- Cast
- Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg, Martin Sheen, Ray Winstone
- Rating
- R
- Genres
- Crime, Documentary, Drama, Thriller
Directed by Martin Scorsese — in the project that finally won him the Academy Award for Best Director, no less — The Departed (2006) should without a doubt go down as the best movie from the 2000s that featured Leo DiCaprio. It may not have been his most impressive performance of the bunch, but there should be no denying the quality of the project as a whole. It follows DiCaprio’s character William “Billy” Costigan opposite Colin Sullivan (played by Matt Damon) as the former is sent to infiltrate the workings of an Irish mob boss named Jack Costello — of course, he’s portrayed by Jack Nicholson.
Costello essentially raised Colin (again, Damon’s character) to become the perfect mole as an adult, creating a symmetry with Leo’s character as Colin infiltrates the Massachusetts State Police. The overall product twists and turns just as seamlessly as its performers deliver the film’s dulcet dialogue, with others like Mark Wahlberg, Vera Farmiga, Alec Baldwin, and Martin Sheen also featured herein. And in the end, it’s those acting efforts in tandem with technical mastery regarding camerawork, film editing, and everything in between that helped The Departed come out on top. It’s arguably the best film from everyone involved, regardless of decade, and ultimately tops the list.
Stream on Fubo
