Every great actor has to start somewhere. And yes, Leonardo DiCaprio is among the best. Despite a reputation as solely a film actor, DiCaprio actually began his career with minor roles on shows such as The New Lassie and The Mickey Mouse Club. It wasn’t until the early 1990s that DiCaprio really burst onto the big screen. He defied the odds and remained booked and busy, starring in a total of 11 movies throughout the decade.
Consider, for example, What’s Eating Gilbert Grape, his third movie, which earned him an Oscar nomination for Best Supporting Actor. This is a feat in itself. Of course, not every movie is a success, but that’s part of the process. From lesser-known entries (Critters 3) to now-classics (Titanic), which Leonardo DiCaprio movie from the 1990s is the best?
11
‘Critters 3’ (1991)
Critters 3, as the title suggests, is a sequel to the two prior Critters films released in the 1980s. In this entry, a family is overtaken by monstrous creatures who hide themselves in their car and home. When the Critters wreak total havoc, it’s up to Josh (DiCaprio) and his friends to stop the Critters before it’s too late. Can he do it?
DiCaprio’s first (unofficial) movie was not a blockbuster by any means. The direct-to-video entry is described as a “sci-fi comedy horror.” Considering its 90-minute runtime, there’s a lot going on. However, Critters 3 is a fever dream on par with many horror movies of the time, earning a 0% rating on Rotten Tomatoes. It may not be a good movie, but it’s a fun watch (and where DiCaprio got his start).
10
‘Total Eclipse’ (1995)
While it is not entirely historically accurate, Total Eclipse tells the fated story of real-life French poets, Arthur Rimbaud (DiCaprio) and Paul Verlaine (David Thewlis). The movie is set in 19th-century France and is loosely based on letters and pieces of writing exchanged between the two despite the presence of Rimbaud’s wife, Mathilde Maute (Romane Bohringer).
It’s defined as an “erotic historical fiction” touching upon themes of sexuality and desire infused with the arts. What is the proper relationship between these two artists in light of the political, social, and economic tribulations throughout the country? Just 19 years old at the time, the film utilizes DiCaprio’s youthful appearance and demeanor in juxtaposition to his exceptional talent as an accomplished poet with a yearning for love.
9
‘The Quick and the Dead’ (1995)
The Quick and the Dead is a tale of life and death in the wild west. The story follows Gunslinger Ellen (Sharon Stone), who enters the town of Redemption, seeking to avenge her father’s death at the hands of the town’s mayor. Luckily, a quick draw is taking place, giving Ellen the chance to do just that. But there’s another entrant who is also intent on killing the mayor — known throughout the town as “The Kid” (DiCaprio).
The movie boasts a fascinating plot and an equally fascinating town, aptly named Redemption. It’s a classic Western filled with themes of revenge, morality, and the law’s obstruction. The Quick and the Dead was recently added to Netflix, where it experienced a surge in viewership, serving as a testament to the movie’s renewed interest.
8
‘This Boy’s Life’ (1993)
Based on Tobias Wolff‘s eponymous autobiography, This Boy’s Life is a tragic tale set in the 1950s. After a series of events leads Caroline (Ellen Barkin) and her son, Tobias (DiCaprio), to live in Washington State, their presumably idyllic escape leads her to meet and marry Dwight Hansen (Robert De Niro). However, not all is what it seems as their household grows increasingly tumultuous due to Dwight’s abusive behavior towards both Caroline and Tobias.
But This Boy’s Life goes deeper; it’s a reflection of the time period and what women were expected to endure to have a comfortable life. Unfortunately, this puts both mother and son at risk in the process. This is where DiCaprio’s talent truly shines, portraying both a supportive son and a distraught boy as a result. Additionally, This Boy’s Life marks a few firsts: DiCaprio’s first feature film lead role, the first of three times DiCaprio and De Niro star alongside each other.
7
‘The Man in the Iron Mask’ (1998)
DiCaprio is known for his roles in historical films, whether fiction or based on true stories. The Man in the Iron Mask is no different. Just one year after the record-breaking Titanic, DiCaprio took on dual roles in this movie that follows four musketeers living under the reign of King Louis XIV.
While nothing could top the former, The Man in the Iron Mask proved he was more than just a one-hit-wonder actor. It can be challenging to portray two characters in one movie, but DiCaprio did so in stride. The Man in the Iron Mask was met with mixed reviews but was a box office success, perhaps due to the names attached to the production.
6
‘Celebrity’ (1998)
This Woody Allen-directed movie often goes unnoticed — it wasn’t one of his strongest films. Writer and husband Lee Simon (Kenneth Branagh) attempts to turn his life around by becoming an entertainment journalist, divorcing his wife, Robin Simon (Judy Davis), in the process. But as it turns out, a change in scenery can’t fix anything. If anything, it made things worse.
As the movie progresses, Lee indulges in the extravagance of New York City pomp and circumstance. As all this takes place, Robin is introduced to the true celebrity lifestyle. While DiCaprio’s role is minimal in comparison to his other movies from this era, it’s impressive to share the screen with big names—a sign of what’s to come in his fruitful career. Unfortunately, Celebrity bombed at the box office, so this did not help (or hurt) DiCaprio’s reputation.
5
‘The Basketball Diaries’ (1995)
Jim Carroll (DiCaprio) is the star player on his high school basketball team. But he ultimately succumbs to the pressure of his mother and coach. As a result, Jim turns to drugs to cope. Things escalate when he and his friends resort to obtaining drugs by any means. Can one man inspire him to turn his life around?
Despite its title, The Basketball Diaries is more about the trials of success and deep failure than it is about basketball. Yes, it’s a sports film like any other. But The Basketball Diaries explores something more profound.
4
‘Marvin’s Room’ (1996)
Bessie (Diane Keaton) and Lee (Meryl Streep) are estranged sisters with a dysfunctional family history. When Bessie is diagnosed with cancer, she must reunite with her estranged sister for medical help. It’s a tale of forking paths and how this splits a family apart. So while they do come together — two decades later — there is an added layer of complexity. De Niro plays the doctor who treats Bessie during this process.
DiCaprio stars alongside the three A-listers as Bessie’s son, Hank. He, too, has faced challenges in life that Bessie must fathom. Yet another of the actor’s films from this decade in which he takes on the role of a troubled teen. Above all else, Marvin’s Room is a story about family and the need for support despite dysfunction.
3
‘Romeo + Juliet’ (1996)
There are numerous adaptations of Romeo and Juliet, thanks to its timelessness. We all know the story: Romeo and Juliet come from feuding families but are destined to fall in love, leading to a romance that is both beautiful and tragic. Instead of fair Verona, Romeo + Juliet is set in the fictional Verona Beach, California, during the 1990s. And rather than two noble families, they are instead opposing mafia families.
They speak in Shakespearean prose but dress in modern clothing. The context of the West Coast conflict is marked by crime and corruption. Romeo + Juliet succeeds because of the era in which it was released. Directed by Baz Luhrmann (Moulin Rouge!, The Great Gatsby, etc.), the movie is a testament to his creativity in unconventional storytelling.
2
‘What’s Eating Gilbert Grape’ (1993)
The movie follows the titular Gilbert Grape (Johnny Depp) and his experience living with and taking care of his family members. Gilbert’s mother cannot leave home due to her medical obesity. Meanwhile, his brother Arnie (DiCaprio) was born with a mental disability that leaves him unable to care for himself. Despite this, Gilbert attempts to maintain a relatively everyday life by working at the local grocery store and having a girlfriend.
It’s a running joke that DiCaprio has never won an Oscar, despite receiving numerous nominations in the Best Actor category over the years. This sentiment began as early as 1993 with What’s Eating Gilbert Grape, where he was nominated for Best Supporting Actor but ultimately lost. Thankfully, DiCaprio finally received his accreditation for The Revenant in 2016.
