Leonardo DiCaprio is no doubt one of the greatest actors of this generation. While he received worldwide recognition for his role in Titanic, the 2000s saw the acclaimed actor break away from being just known as a teen heartthrob and cement himself as one of the best actors in Hollywood.
While it wasn’t until 2016 that he won his first Oscar, the 2000s highlighted DiCaprio’s versatility and incredible range through his bold and diverse roles. It’s no surprise that most of his movies released in the 2000s received high IMDb ratings, and many of these performances will no doubt go down as some of his best.
9 Don’s Plum (2001) – 5.7
If there’s such a thing, Leonardo DiCaprio’s character Derek in Don’s Plum is one of his lesser-known roles. Also starring Tobey Maguire and Kevin Connolly, the low-budget indie film tells the story of a group of 20-somethings who gather at a restaurant called “Don’s Plum” every Saturday night – and that’s about as far as the plot goes.
The highly improvised movie was filmed over six days between July 1995 and March 1996, however, wasn’t released theatrically until 2001. Rumors have swirled about the movie over the years, with DiCaprio and Maguire reportedly not wanting it released at all, as reported by The Guardian. Due to its legal implications, the film was banned in the US and Canada (Republic World).
8 The Beach (2000) – 6.7
After the unimaginable success of Titanic, there were high expectations for Leonardo DiCaprio’s next film. Unfortunately, The Beach didn’t come close to matching the success of Titanic. In the Danny Boyle drama, DiCaprio stars as a young adventure-seeking traveler named Richard who is in search of a legendary island paradise.
The dystopian drama was considered a flop when it came out and severely underwhelmed at the box office. While Leonardo DiCaprio is no doubt one of the greatest actors the world has ever seen, this movie is often forgotten among his success.
7 Body Of Lies (2008) – 7.1
The acclaimed Ridley Scott has directed countless classics, so when it came to an action thriller starring Leonardo DiCaprio and Russel Crowe with Scott at the helm, it was ensuing to exceed expectations given the talent behind it. Unfortunately, Body of Lies failed to stand out, despite its huge potential.
DiCaprio plays Roger Ferris, a CIA agent who is operating in the Middle East trying to capture a radical Islamic terrorist. it’s often overlooked, that’s not to say it isn’t good and is simply one of the great Leonardo DiCaprio movies that many have never heard of. There is plenty of action with a consistently well-paced narrative, with both DiCaprio and Crowe giving convincing performances.
6 Revolutionary Road (2008) – 7.3
Eleven years after the release of Titanic, Leonardo DiCaprio and Kate Winslet reunited onscreen for the first time in the romantic drama, Revolutionary Road. The Titanic pair made for one of the most iconic movie couples of all time, so it’s no surprise that fans were quick to compare Winslet and DiCaprio’s onscreen romance in Revolutionary Road.
The story follows Frank and April Wheeler, a struggling husband and wife who try and cope with the breakdown of their marriage. The movie received generally positive reviews and while it’s not one of DiCaprio’s most notable films, his convincing portrayal of the smooth-talking salesman is up there with his best.
5 Gangs Of New York (2002) – 7.5
Martin Scorsese and Leonardo DiCaprio are one of Hollywood’s greatest duos and Gangs of New York is the film that marked their first collaboration together. Set in 1863, DiCaprio plays the Irish catholic Amsterdam Vallon, who plots revenge against the man that murdered his father.
Based on Herbert Asbury’s novel of the same name, the film also features Daniel Day-Lewis as a brutal gang leader and Cameron Dias as an Irish immigrant. While the movie received generally positive reviews, many believe that DiCaprio was outshined by the captivating performance of Daniel Day-Lewis, for which he received an Oscar nomination.
4 The Aviator (2004) – 7.5
The next collaboration between Martin Scorsese and Leonardo DiCaprio was The Aviator, and this time, the stakes were raised. DiCaprio took on the titular role of Howard Hughes, a billionaire filmmaker and aviator whom many believe is one of the best main characters in a Scorsese movie,
Starring alongside Cate Blanchett and Kate Beckinsale, DiCaprio plays Hughes in the height of his fame, while depicting his deteriorating mental health and severe OCD. DiCaprio’s accurate portrayal of the eccentric tycoon was flawless and earned him his first Oscar nomination since What’s Eating Gilbert Grape.
3 Blood Diamond (2006) – 8.0
Starring Leonardo DiCaprio and Djimon Hounsou, Blood Diamond follows the story of Rhodesian smuggler and mercenary Danny Archer, who forms an unlikely team with local fisherman Solomon Vandy. Set during the Sierra Leone Civil War, the two embark on a dangerous mission as they hunt to recover a rare diamond.
The war thriller received positive reviews and highlighted the brilliant performances of both DiCaprio and Hounsou. To accurately play a Rhodesian-now-Zimbabwean native, DiCaprio had to act with a South African accent, and despite the accent remaining divisive among fans, the role garnered the actor with his third Oscar nomination.
2 Catch Me If You Can (2002) – 8.1
Directed by the legendary Steven Spielberg, Catch Me If You Can depicts the story of Frank Abagnale Jr., one of the most successful con men in American history. The brilliant cat and mouse caper stars Leonardo DiCaprio as Frank and Tom Hanks as FBI agent Carl Hanratty, who makes it his mission to capture the young con artist, while also harboring a level of respect for him.
The movie perfectly captures DiCaprio’s boyish charm and has produced one of his most likable characters to date. Spielberg’s genius and seamless direction tells the real-life story in a light-hearted and comical manner, while DiCaprio’s performance showcased his incredible range as an actor.
1 The Departed (2006) – 8.5
Martin Scorsese remains one of the most talented directors of all time, yet somehow, he had to wait until 2006 to receive his first Oscar. Featuring a star-studded ensemble of Leonardo DiCaprio, Jack Nicholson, Mark Wahlberg, and Matt Damon, The Departed follows Billy Costigan, a Boston Police trainee who is sent undercover to infiltrate mobster Frank Costello’s crew.
The story of good-cop-bad-cop is violent, funny, and most importantly, a warning that no one can be trusted in this dark world of crime. The Scorsese masterpiece is up there with the greatest gangster movies of all time and is living proof of why he will always be king of the gangster genre.
