Leonardo DiCaprio‘s best movies are a mix of his comedic and dramatic skills, and a bit of action on the side. He’s versatile and transformative, capable of embodying his roles and researching them methodically, with a lot of dedication; that’s why he’s considered one of the greatest actors of today. Although he has a long and interesting filmography sitting in a wide variety of genres, his most famous movies tend to be dramas.
Whether he portrays a poor kid falling for a wealthy girl or a man returning from war, DiCaprio has some incredibly memorable dramatic roles and movies. If you’re less into his action and thrills and more into the dramatic, heavier stuff, here are Leonardo DiCaprio’s five greatest drama movies.
5
‘Revolutionary Road’ (2008)
Revolutionary Road marks DiCaprio’s second collaboration and reunion with Kate Winslet, with whom he starred in Titanic for the first time. Revolutionary Road feels like “what would have happened if Jack and Rose stayed together,” though it’s a much less romantic and a lot more realistic and sad story about the evolution of a marriage. Initially, the two were reluctant to play a couple again after Titanic, for the exact fear of being equated to Jack and Rose, but in Revolutionary Road, they show incredible maturity and progress from their first collab. Sam Mendes directed this film, which was based on Richard Yates‘ 1961 novel of the same name; the movie was meant to be made that same year, which must be one of the longest noted “limbo periods” for a movie, maybe ever.
Revolutionary Road follows a couple throughout the 1940s and 1950s as their marriage falls apart due to heavy personal problems and dissatisfaction. In 1948, longshoreman Frank Wheeler meets aspiring actress April, and the two soon fall in love and marry. They move to a suburban area, meeting their neighbors, Shep (David Harbour) and Milly (Kathryn Hahn), and befriending their realtor, Helen (Kathy Bates); on the surface, they seem happy and harmonic, but Frank is tired of his mundane job, while April isn’t successful at getting acting gigs. Their personal dissatisfaction seeps into their relationship, turning it into a strained push and pull of emotions. Revolutionary Road is a difficult film but an interesting, visually gorgeous, and play-like drama worth watching. It’s also kind of underrated, considering its biggest selling point at one moment was DiCaprio and Winslet’s reunion. While their chemistry from the first collab remains, Revolutionary Road sees DiCaprio as the slightly better performer of the two, with intense dedication and vulnerability on display.
4
‘The Basketball Diaries’ (1995)
The Basketball Diaries is an early film that wasn’t the most critically acclaimed but is, upon reassessment, a vital film for both the 1990s and DiCaprio’s emerging career at the time. It’s a biographical crime drama based on the autobiographical novel by Jim Carroll, who, in the book, reflects on his promising basketball career and its inevitable demise after developing a drug addiction as a teenager. The Basketball Diaries is Scott Kalvert‘s feature directorial debut, and it’s a grim and heavy story that attempts to deliver a cautionary tale while staying packed into quintessentially grunge/90s packaging, evoking the lives of so many artists who succumbed to drug addiction at the time. Even the soundtrack is packed with grunge legends, like Pearl Jam, Soundgarden, and The Cult, with Carroll himself contributing his musical artistry to it. Whatever you feel about The Basketball Diaries, it’s a star-making film for DiCaprio, who is magnetic in it.
The Basketball Diaries follows Jim Carroll as a high schooler in NYC, taking part on the school’s basketball team and hanging out with his best friends, Pedro, Mickey, and Neutron (James Madio, Mark Wahlberg, and Patrick McGaw, respectively). Jim and his friends begin taking recreational drugs at school, and while no one notices at first, they soon begin showing bigger signs of addiction until they begin living on the street, begging for money and doing anything to get their next fix. Jim, privately, is artistic and enjoys writing and poetry, which soon helps him get better and get clean (spoiler, but Carroll was an adult at the time of making the film, so you could’ve guessed twice). The Basketball Diaries is a pretty realistic portrait of youth when it’s affected by addiction, and while it may not be pleasant to watch, it’s an incredible and essential film among DiCaprio’s dramas.
3
‘Killers of the Flower Moon’ (2023)
The sixth collaboration between DiCaprio and Martin Scorsese happened in 2023, in Scorsese’s latest film, Killers of the Flower Moon. The seventh is coming up with What Happens at Night, which is currently filming, and there’s a short film from 2015 that stars DiCaprio and Robert De Niro as the two actors argue over who gets to make another film with Scorsese. Both starred in Killers of the Flower Moon, and while De Niro is the meanie, DiCaprio isn’t exactly the most positive character in the film, either. Both, as brilliant and impressive as they are, give way to Lily Gladstone to shine as the lead; sometimes, a great actor also knows when to pull away to give others a chance, which just makes them all the more iconic. Killers of the Flower Moon is based on real-life events that took place in Oklahoma during the late 1910s and early 1920s, when members of the Osage Nation of Oklahoma struck oil, became rich through mineral rights, and were killed off in brutal ways.
Killers of the Flower Moon opens with the story of the people of the Osage Nation discovering oil on their land, which made them wealthy at the time. However, the law needed their land to be “run” by white residents, as they were deemed incompetent; enter William Hale King (De Niro), who posed as a benefactor to the Osage Nation. After his nephew Ernest (DiCaprio) returns from WWI to live with him on his estate, William introduces him to Mollie Kyle (Gladstone), whose family has rights to the wealthy land. At first, Ernest is considered to be a mere “gold digger” but falls in love with Mollie, showing their relationship while depicting the growing danger and stress of the Osage murders. While some have considered Killers of the Flower Moon to be exploitative of the tragic narrative of the Osage murders, others found it revelatory, praising Scorsese’s efforts to include members of the Osage Nation today as advisors on the film’s narrative and details.
2
‘Titanic’ (1997)
Of course, the most famous DiCaprio movie has to be Titanic, in which he stars alongside Kate Winslet. For both of them, this was a breakthrough on a global scale, starring in a beautiful but tragic romance that is still widely considered one of the most romantic movies of all time. Titanic also jumpstarted DiCaprio and Winslet’s longtime friendship, after which they collaborated on the same project once more in 2008, Revolutionary Road. James Cameron‘s drama is about the real-life ocean liner, which departed from Southampton, England on April 10, 1912, and sank not even a full five days later after clashing with an iceberg. While this timeline might break the illusion of Jack and Rose’s whirlwind romance, which is arguably one of the greatest romances ever, Titanic is still a celebration of love and life.
Titanic opens with a modern-day crew setting out to find a famous jewel they believe is still in the wreck; they don’t find the jewel, but they do find a sketch of a woman wearing it. After Rose Dawson Calvert reaches out to the crew, telling them she’s on the drawing, the story goes back to 1912, following the maiden voyage of RMS Titanic, with Rose (Winslet) boarding the ship in Southampton with her mother and American fiancé, Cal (Billy Zane). Rose is only 17, and she’s unhappy with her incoming marriage, even contemplating jumping off the ship’s stern. On one such occasion, she is stopped by Jack Dawson (DiCaprio), a poor artist; they begin to bond, becoming friends and quickly falling in love. DiCaprio and Winslet have a beautiful chemistry, and it’s hard to tell who is better out of the two; it’s like they bring the best out of each other, giving dedicated, intense, and beautiful performances.
1
‘What’s Eating Gilbert Grape’ (1993)
The film that earned DiCaprio national acclaim and the title of “one to watch out for” is What’s Eating Gilbert Grape. He stars as the titular Gilbert’s younger brother, Arnie, who has a mental disability; he was so convincing in the role that, at 19, he was nominated for the Best Supporting Actor Oscar. The role of Arnie was meant to go to Corey Feldman and then Christian Bale, but while the former had issues with Johnny Depp, the latter simply couldn’t measure up to DiCaprio’s audition. He prepared for Arnie by spending time with mentally disabled kids and teens, watching them and hanging out with them to understand their lives. What’s Eating Gilbert Grape is a well-known star-maker of a film; it most notably allowed DiCaprio to find his footing in Hollywood.
What’s Eating Gilbert Grape follows the eponymous Gilbert Grape (Depp), who lives with his mother Bonnie and three out of four siblings, spending the most time with the mentally disabled Arnie. Gilbert works at a local grocery store, caring for his family full-time since his mother, grief-stricken, became obese and homebound. Caring for Arnie, his sisters, and his mother leaves Gilbert with little time for a private life; one day, he meets Becky (Juliette Lewis), and she befriends him and Arnie, helping Gilbert find himself. It’s quite a dramatic coming-of-age film, and it’s hard to watch Gilbert’s life sometimes. Although some critics have found the film predictable, it’s been lauded over and over for its immense charm and warmth, including DiCaprio’s stunning performance, which is often used to describe his talents from an early age.
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