His other movies might have your curiosity, but these ones will have your attention.
Starting out as a teenage actor in the early 1990s, Leonardo DiCaprio rose in prominence throughout the decade, becoming one of the most recognizable actors of his generation by the end of it. Since 2000, he’s continued to dominate, and even won over naysayers who may have dismissed him early on as being “just” a teen star getting by on his looks. He grew a reputation for being fearlessly dedicated to the roles he took on, and for becoming more selective with his projects, leading to gaps of many years between some of his starring roles (like with 2015’s The Revenant being his last feature film until 2019’s Once Upon a Time in Hollywood).
The general high quality of the movies he’s appeared in makes selecting underrated titles a little tricky, and even necessitates picking a few that are relatively well-known. However, something can be underrated if it’s generally thought of as being “good” when it’s actually great, and DiCaprio’s earlier years – when he was taking on more frequent roles – do contain some titles definable as underrated in the traditional sense.
‘Body of Lies’ (2008)
Director: Ridley Scott
While it’s hard to call Ridley Scott’s body of work consistently great, it is easier to call it diverse and maybe even all-encompassing. Body of Lies is one of his films that’s become somewhat forgotten in time, even though it’s certainly not terrible overall, and does have two well-regarded stars in the lead roles: Leonardo DiCaprio and Russell Crowe.
Body of Lies is a spy thriller about the CIA’s attempts to track down the individual behind a series of deadly attacks, with DiCaprio playing the agent who actually has to get involved in the dangerous situations and Crowe playing someone who observes things from afar, communicating with DiCaprio all the while. Their dynamic is solid, and the film is slick and moves along fast enough to be watchable in the moment, even if it doesn’t prove to be super memorable once it’s all over.
‘J. Edgar’ (2011)
Director: Clint Eastwood
Those who don’t mind straightforward biopics will probably get something out of J. Edgar, a noteworthy film for pairing Leonardo DiCaprio with the ever-prolific Clint Eastwood, serving as director here. DiCaprio relishes the chance to play a well-known historical figure, J. Edgar Hoover, with the film covering numerous decades and focusing particularly on Hoover’s role as the first Director of the FBI.
Some of the film feels a little routine narratively and visually, with a somewhat sluggish pace considering the whole thing’s well over two hours. However, J. Edgar does offer a relatively strong lead performance from DiCaprio, even if it’s not quite one of his very best (neither can it be counted among Eastwood’s best achievements). Also, it’s marginally more interesting to watch it in a post-Killers of the Flower Moon world, given that film name-drops J. Edgar Hoover, has a narrative tied to the creation of the FBI, and also stars DiCaprio (not as Hoover, though).
‘The Beach’ (2000)
Director: Danny Boyle
Before making 2002’s 28 Days Later and 2010’s 127 Hours – the latter of which might be more horrific, despite containing no zombies – Danny Boyle also directed The Beach, which is another offbeat and uneasy thriller from the filmmaker. DiCaprio’s character, a young man named Richard, travels to Thailand and then finds what could be called a modern-day treasure map of sorts, which sets him off on an unexpectedly dangerous adventure to find the area marked on the map.
It’s the sort of film that wasn’t loved – at least critically – upon release, but has received some more recognition as the years have gone along, particularly since DiCaprio revealed his depths as an actor during the 21st century. Perhaps the world wasn’t quite ready for DiCaprio to leap into more challenging roles yet, arguably demonstrated by the fact that the ever-exasperating Razzies nominated him for “Worst Actor” for his role in The Beach.
‘The Man in the Iron Mask’ (1998)
Director: Randall Wallace
With its casting choices and the fact it uses some very well-known literary characters in its plot, The Man in the Iron Mask is certainly ambitious, though it doesn’t quite hit a home run. Still, it’s hard not to admire some of the creative risks it takes, and there’s a certain amount of enjoyable swashbuckling action and old-fashioned drama to be found here for those in the mood for such things.
‘This Boy’s Life’ (1993)
Director: Michael Caton-Jones
As a film, it does get a little much at times, as though it’s based on a real-life story, there are certainly parts of This Boy’s Life that feel simplistic and a bit Hollywood, for lack of a better word. Yet De Niro gives a memorably mean performance, and DiCaprio is excellent considering his age, with the movie ultimately being worth watching for the fact it pairs these two actors alone.
‘The Quick and the Dead’ (1995)
Director: Sam Raimi
Surprisingly, Leonardo DiCaprio ranks among one of the highest-earning Western actors of all time, with 1995’s The Quick and the Dead playing a role in that. DiCaprio himself has only been in three Westerns, but The Revenant and Django Unchained were both very successful at the box office, and The Quick and the Dead… well, this one wasn’t as successful, but it’s still surprisingly good, and deserved a little more love from audiences when it was released.
It’s a rather chaotic Western about various outlaws taking part in a very high-stakes dueling competition in a small town filled with people who know their way around a pistol. DiCaprio was noticeably young here, but he gives a strong performance alongside an amazing cast of older actors, with the likes of Sharon Stone, Gene Hackman, Russell Crowe, and Lance Henriksen all impressing, too.
‘Revolutionary Road’ (2008)
Director: Sam Mendes
Reuniting Leonardo DiCaprio and Kate Winslett just over a decade on from the Best Picture-winning romantic epic that was Titanic, Revolutionary Road is also a romance movie, but of a different sort. It’s set in the 1950s and sees the pair playing a married couple living with two children in the suburbs, dealing with all sorts of family drama and navigating the ups and downs of an adult relationship.
Revolutionary Road is pretty heavy-going, and does feel decidedly character-focused, meaning those in search of a complex or intricate story aren’t likely to find it here. It gets by thanks to the performances from DiCaprio and Winslett, as well as key supporting actors like Kathy Bates (who was also in Titanic, of course), and Michael Shannon, the latter of whom was Oscar-nominated for his role in the movie.
‘What’s Eating Gilbert Grape’ (1993)
Director: Lasse Hallström
This Boy’s Lifewasn’t the only coming-of-age movie released in 1993 that Leonardo DiCaprio appeared in, as he also had a key supporting role in What’s Eating Gilbert Grape, a movie that earned DiCaprio his first Oscar nomination. The titular character is played by Johnny Depp, with the movie following how he tries to care for his family during hard times.
DiCaprio plays this character’s younger brother, Arnie, who has autism, with this casting choice potentially being controversial when viewed by today’s standards. DiCaprio does still approach the role with care, and it’s easy to imagine that the depiction of such a character could’ve gone far worse. For showing the actor’s abilities from such a young age, and for containing what might be his first great performance, What’s Eating Gilbert Grape is worth checking out.
‘The Basketball Diaries’ (1995)
Director: Scott Kalvert
On top of being another coming-of-age movie starring Leonardo DiCaprio, The Basketball Diaries also functions as an honest and sometimes harrowing look at heroin addiction. Based on a real-life story, DiCaprio plays a teenager whose life spirals when he starts taking the drug in question, with such an addiction proving detrimental to his future as a student and aspiring basketball player.
Certain films about this difficult topic have navigated it with a little more care and nuance than found in The Basketball Diaries, but it’s still solid for what it has to do, and is carried by the strengths of its cast members. Narratively, it hits all the expected beats and doesn’t exactly provide much by way of inspired or surprising choices, but that stuff is sound, and the acting – particularly from DiCaprio – is largely very strong.
‘The Aviator’ (2004)
Director: Martin Scorsese
Some of Leonardo DiCaprio’s most well-known performances can be found in movies directed by Martin Scorsese. There are half a dozen feature films the pair have collaborated on in total, with Gangs of New York, The Departed, Shutter Island, The Wolf of Wall Street, and, most recently, Killers of the Flower Moon, all being acclaimed (even though DiCaprio’s performance in the last of those was strangely overlooked during Oscar season).
Perhaps the least exciting of the Scorsese + DiCaprio movies would be The Aviator, which is underrated by the high standards of a Scorsese + DiCaprio movie, meaning it can get a bit overlooked. It’s a long, dense, but very rewarding watch for those with almost three hours to spare, going so in-depth with its story about filmmaker/businessman/aviation pioneer Howard Hughes that it starts to feel almost like a psychological drama at points. It looks typically slick, being up to Scorsese’s usual standards, and DiCaprio’s performance is admirably dedicated, making it an all-around very good film.
