When a young Leonardo DiCaprio first appeared in Critters 3 back in 1991, few could have predicted that he would go on to become one of Hollywood’s biggest stars. Three decades later, however, and that’s exactly what he is. He’s won and been nominated for numerous awards and has appeared in some of the biggest movies of the era. Not all of them have been winners, but they tend to hit the mark more often than not.
Even those that fail to make much of an impression with critics tend to perform well at the box office; with titles like Romeo + Juliet, Shutter Island and Gangs of New York all generating a healthy return on their initial budgets. There’s an argument to be made that much of that is down to DiCaprio himself, whose standout performances and boyish good looks continue to make him one of the biggest draws in the industry.
10 What’s Eating Gilbert Grape (1993) - 73
After his brief appearance in Critters 3, a young Leonardo DiCaprio soon found himself starring alongside Robert De Niro in the 1993 title This Boy’s Life. The movie failed to make much of an impact with critics, but it was enough to earn DiCaprio the role of Arnold Grape where he once again starred alongside one of Hollywood’s biggest names.
At that time, however, Johnny Depp’s career was also in its infancy with the role of Edward Scissorhands having been his only one of real note. What’s Eating Gilbert Grape is fairly forgettable when compared to the aforementioned title, but it still provides a compelling narrative even in spite of its predictability. Both actors would go on to bigger and better things, but it’s here that the foundations for DiCaprio’s later successes were first laid.
9 Inception (2010) - 74
Inception can be incredibly confusing at times. So much so, in fact, that during a 2020 appearance on Marc Maron’s WTF podcast the movie’s leading man confessed that he still couldn’t wrap his head around the movie more than a decade on from its release. One suspects that he’s not alone in that regard, with some critics complaining about its over-complicated plot.
Regardless of how one views the story though, it’s hard to argue that the movie doesn’t look fantastic. The cinematography on display is first class and makes for one of the most visually impressive movies ever made. It is exactly what one might expect from a Christopher Nolan movie and definitely worth checking out at least once. Most will probably need to watch it a few more times though if they want to fully understand it.
8 Catch Me If You Can (2002) - 75
Despite his deceitful actions throughout the movie, there’s something incredibly likable about Frank Abagnale Junior. The confidence that DiCaprio brings to the role certainly helps in that regard, but it’s perhaps his relationships with both his father and the man trying to catch him that contribute the most. Ultimately, they make the character relatable which isn’t always easy when said character also happens to be a criminal mastermind.
Christopher Walken and Tom Hanks are both fantastic in the movie as well, but it’s arguably the former who deserves the bulk of the acclaim. He was able to fully capture the essence of his character and stole the show despite his relatively minor role in the movie. He was rewarded for his efforts with an Academy Award nomination which is, somewhat surprisingly, one of only two that he’s received throughout his long career.
7 The Wolf Of Wall Street (2013) - 75
The Wolf of Wall Street is a fairly controversial movie not just because of its content, but also due to some of the questions surrounding its funding. One thing that most can agree on, however, is that DiCaprio’s performance as Jordan Belfort is both entertaining and compelling. It was arguably one of the driving factors behind the movie’s critical and commercial success and really helped to demonstrate his incredible range.
Based loosely on a true story, the movie provides viewers with one hell of a ride; evoking a wide range of emotions throughout its three hour duration. There are times when it’s vulgar, others when it’s hilarious and some when it’s just downright tragic. The way that it flicks so effortlessly between these states is a testament to the wonderful talent of all of those who were involved with the production - even Jonah Hill!
6 Titanic (1997) - 75
Although DiCaprio had found moderate notoriety through his performances in the likes of The Quick and the Dead and Romeo + Juliet, it was not until he landed the role of Jack in Titanic that he really became a household name. The ill-fated ship may have been on a course for disaster, but it propelled the young actor’s career into the stratosphere and cemented his place as a leading man.
Although it has since been overtaken, at the time of its release it was the highest grossing movie of all time and still shares the records for both most Oscar nominations and most Oscar wins with 14 and 11 respectively. DiCaprio didn’t receive a nomination for his performance in the movie although was singled out for praise by numerous critics. That’s not too bad, considering he was just 20 when he landed the part.
5 The Revenant (2015) - 76
Depending on who you ask, The Revenant is either a cinematic masterpiece or a self-absorbed snooze-fest. Thankfully for Leonardo DiCaprio, the judges at the Academy Awards seemingly disagreed with the former assessment and deemed his performance worthy of the Best Actor award. Prior to that, he’d been nominated for the accolade on three separate occasions but had failed to bring home the prize on each one.
Most will remember this as the movie where Leonardo DiCaprio goes one on one with a bear, but there’s a lot more to it than that. It’s a story about surviving the harsh reality of frontier life with a dash of revenge sprinkled on top for added flavor. It paints a bleak picture of the period, but one that manages to be both enthralling and entertaining throughout the majority of its two and half hour runtime.
4 The Aviator (2004) - 77
DiCaprio’s appearance in The Aviator was one of his first serious roles as well as the first of four movies that he starred in to premiere on Christmas Day. It was also the second time that the young actor worked with Martin Scorsese, having first done so on the set of the 2002 title Gangs of New York. As was perhaps to be expected of a biopic based on the life of Howard Hughes though, the tones of the two movies differ quite drastically.
The movie was mostly enjoyed by critics, with many praising its use of color and the attention to detail that was paid when recreating the period in which the movie is set. It went on to win five Academy Awards from 11 nominations as well as four BAFTAs, making it one of Scorcese’s most acclaimed titles. It might not have been enough to win Best Director, but he wouldn’t have to wait too much longer for that honor.
3 Django Unchained (2012) - 81
Were it not for Will Smith’s insistence that Django be the one to kill Calvin Candie, Django Unchained may have been a very different movie. Thankfully, Tarantino stuck to his guns and Jamie Foxx was cast as the titular character instead. The rest, as they say, is history. The movie went on to become one of the director’s most successful; both in terms of the critical acclaim that it received and its box office takings. Leo may not have been the lead, but he definitely played his part in that success.
He was cast as the movie’s main antagonist, a wealthy slave owner named Calvin Candie who stands between Django and his freedom. Given the sensitivity of the subject matter, everybody involved did a wonderful job of bringing Tarantino’s screenplay to life without it ever feeling too disrespectful. Of course, the movie features its fair share of violence, but also manages to be both thoughtful and emotive in its storytelling.
2 Once Upon A Time… In Hollywood (2019) - 83
While some may not have cared too much for its meandering narrative, the acting on display in Once Upon a Time… in Hollywood really is fantastic. Given some of the huge names who appear in the movie though, that was always to be expected. The fantastic chemistry between DiCaprio and Brad Pitt, on the other hand, was a somewhat welcome surprise.
Considering the inspiration for the movie and the man sat in the director’s chair, that the movie had a violent ending should not have shocked viewers. The events that transpired, however, serve as a great example of how to subvert expectations and also provided a much happier ending to the tale than the one that played out back in the late-sixties. Not everybody will enjoy it, but fans of Quentin Tarantino should have no trouble enduring its 161 minute runtime.
1 The Departed (2006) - 85
While certainly not a bad movie, it’s crazy to think that The Departed remains the only one for which Martin Scorsese has won the Academy Award for Best Director. As well as some stellar directing, the movie also features some impressive performances from DiCaprio and his co-stars Matt Damon, Jack Nicholson and Mark Wahlberg.
The movie is a loose remake of the 2002 title Infernal Affairs and has an incredibly engrossing plot. The shot composition and sequencing on display are absolutely top notch and are perfectly complemented by the movie’s wonderful soundtrack. It’s far from Leo’s best performance, but his portrayal of Billy is solid and offers more than enough to make the character feel genuine.
NEXT: 10 Classic Directors Who Could Make The Perfect Red Dead Redemption Movie
