5 Most Underappreciated Leonardo DiCaprio Roles

Joseph Wilbur

Today we celebrate the birthday of Leonardo DiCaprio, the star of over 35 films including the second highest grossing film of all time (Titanic). While DiCaprio finally earned himself an Academy Award this year, over the course of his career, he has been nominated for nearly 200 awards. However, not every one of Leonardo DiCaprio’s roles has been so high profile. So, as the accomplished actor and avid environmentalist turns 42 today, we’re taking a look at five of his most underappreciated roles.

Shutter Island (2010)


When you think of a Scorcese film, Shutter Island is not what comes to mind. It’s a good movie, one that cuts closer to horror than anything Scorcese has ever done (that includes Cape Fear, if only by a razor-thin margin). But its mixed reception probably would’ve skewed a bit more positive if Scorcese wasn’t a master of cinema. This kind of pulpy genre storytelling isn’t what people expect from Scorcese. Shutter Island lacks his trademark crackling energy and goes for gut-twisting tension.

Leonardo DiCaprio plays the film’s lead: U.S. Marshal Teddy Daniels, who arrives with his partner (Mark Ruffalo) on Shutter Island in Boston Harbor. Daniels is there to investigate a disappearance — a patient from the Ashecliffe Hospital for the Criminally Insane has vanished without a trace. As Daniels uncovers an apparent conspiracy, bizarre flashbacks test his sanity. To say any more would be too much because the joy of Shutter Island is in discovering the clues and turns through Teddy’s eyes.

DiCaprio plays Teddy with a thick Boston accent that even Matt Damon would admire. He plays it all behind an unhinged glare and a pinched expression, barely containing a rending pain. This isn’t a big prestige role. The dramatic potential is there, but Daniels doesn’t lend himself to ostentatious monologuing or extreme physicality. So DiCaprio is there to react, and like Scorcese, he’s a master of the reaction shot. [Travis Newton]

This Boy’s Life (1993)

When thinking of a Leonard DiCaprio roles, you probably don’t think of his third ever starring role. Only a teenager when filming This Boy’s Life, the performances from the two highest paying actors in the film (Robert De Niro and Ellen Barkin) pale in comparison to DiCaprio’s portrayal of a character who has trouble navigating a dysfunctional household.

The film follows DiCaprio as Tobias “Toby” Wolff and his mother, Caroline (Ellen Barkin), as they move to Washington. There, Caroline meets Dwight, and the two fall in love and marry. However, not all is well, as Dwight’s manner of fathering his stepson has a rather violent twist. With Caroline unwilling to give up her marriage to protect her son, Toby has to plan a way to escape his abusive family. [Joseph Wilbur]

Django Unchained (2012)

leonardo dicaprio in django unchained

Leonardo DiCaprio usually plays someone you can root for. Whether it’s Gilbert Grape, the undercover cop in The Departed, or Jack in Titanic, Leo’s usually the good guy. In 2012, he shattered that image by playing one of film’s most despicable villains. In his role in Django Unchained as Calvin Candie, a plantation owner and Mandingo fight operator, DiCaprio is menacing and vile. He owns several slaves and treats them worse than most people treat animals.

DiCaprio really committed to his Django role. During a scene where he is explaining the pseudo-science of phrenology, he slams his hand into the table and cuts it on a glass. He actually cut his hand open and required stitches but continued the scene in-character. Tarantino used that cut in the film, and DiCaprio’s intensity despite his wounded hand is incredible.

The actor holds his own alongside two-time Academy Award winner Christoph Waltz and Academy Award winner Jamie Foxx. Every scene DiCaprio’s in, he steals, even when paired with other incredible actors. When Candie finally gets what’s coming to him, it’s deeply satisfying because DiCaprio played him with such skill. He’s a villain we love to hate, and this was the role DiCaprio should have won an Oscar for, not The Revenant. [Danielle Ryan]

Marvin’s Room (1997)

This family drama was seriously overshadowed by the release of Titanic the year after, which catapulted Leonardo DiCaprio into superstardom. Only 22 years old at the time of release, DiCaprio’s role in Marvin’s Room was competing with high-profile co-stars Meryl Streep, Diane Keaton, and, again, Robert De Niro. Leonardo’s role was easily the highlight of the film which is saying quite a lot, considering who his fellow actors were. This movie definitely ranks a respectable notch on DiCaprio’s belt of films.

Leo plays Hank, the troubled son of Lee (Meryl Streep), who was committed to a mental institution for setting fire to his mother’s home. The film follows the story of two daughters, Lee and Bessie, and their estranged family. After suffering a stroke 20 years earlier, Bessie looks after their bed-ridden father while Lee ignores him. However, when doctors diagnose Bessie with leukemia, she has to turn to her sister for a bone marrow transplant. [Joseph Wilbur]

Critters 3 (1991)

leonardo dicaprio in critters 3

Before he was battling bears or declaring himself the “King of the World”, Leo made his feature film debut in this second sequel to the surprise moneymaker Critters. Aimed squarely at a younger audience, Critters 3 is easily the worst entry in the series. But how is Leo? He’s doing the typical kid actor thing, but the script attempts to give him a little depth by throwing in a contentious relationship with his stepfather. It’s welcome in a movie that’s somewhat devoid of interesting character beats.

Although, the real appeal is seeing a baby-faced Leo pretend to be scared of ridiculous puppets. I love the Critters films, and this was a regular rental in my childhood days. However, even I can admit that this one is not great. But man, it sure is fun to watch a future Oscar winner be a silly kid actor in a movie about intergalactic hedgehog monsters. Everyone needs that in their life. [Drew Dietsch]

Joseph Wilbur
Joseph Wilbur was a former writer for Fandom for over 2 years. He primarily wrote about the Arrowverse shows, or the DC and Marvel universes. He is a Star Wars fanatic, and has read every book in the 'Star Wars Legends' Universe (most of them at least twice).
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