Leonardo DiCaprio’s 1990s films present a remarkable evolution of a young actor rising from modest beginnings to major stardom. Throughout the decade, DiCaprio took part in 11 movies, ranging from little-known projects to acclaimed masterpieces, demonstrating his growing craft amid roles that varied widely in success and recognition. His performances in these movies remain a defining factor in his enduring reputation as a leading actor of his generation.
A Rough Start: DiCaprio’s Debut in “Critters 3”
In 1991, DiCaprio appeared in “Critters 3,” a direct-to-video sequel featuring terrifying creatures invading a family’s home and car. The film’s premise is straightforward, with DiCaprio’s character Josh and his friends racing against time to stop the menace. Despite its classification as a sci-fi comedy horror, the movie struggled critically, earning a 0% rating on Rotten Tomatoes and little acclaim. However, it provided DiCaprio with an early platform as he embarked on his cinematic journey.
Exploring Complex Relationships in “Total Eclipse”
1995’s “Total Eclipse” depicted the intense and turbulent relationship between French poets Arthur Rimbaud and Paul Verlaine, with DiCaprio playing the youthful and passionate Rimbaud. Set in 19th-century France, the film intertwined themes of art, sexuality, and desire against a backdrop of political upheaval. While its historical accuracy was debatable, the portrayal emphasized the emotional conflict of two gifted artists navigating personal and societal struggles, highlighting DiCaprio’s ability to embody complex roles early in his career.

Wild West Rivalries in “The Quick and the Dead”
Also released in 1995, “The Quick and the Dead” delivered a classic western narrative centered around a deadly quick-draw competition in the town of Redemption. Sharon Stone’s character, Gunslinger Ellen, and DiCaprio’s character, known as The Kid, both seek vengeance on the corrupt town mayor. The movie combined elements of morality, justice, and retribution in a richly atmospheric setting. Recently seeing renewed interest on Netflix, the film’s intriguing plot and stark western themes continue to captivate new audiences.
Portraying Turmoil in “This Boy’s Life”
“This Boy’s Life” (1993) told the harrowing story of Tobias Wolff’s youth, focusing on the struggles between young Tobias, played by DiCaprio, and his abusive stepfather Dwight Hansen, portrayed by Robert De Niro. Set in 1950s Washington State, the drama explored the domestic tensions and societal expectations that shape family dynamics. DiCaprio’s performance stood out as he depicted a boy torn between loyalty and fear, marking his first feature film lead and beginning his on-screen collaboration with De Niro.
Dual Roles in “The Man in the Iron Mask”
In 1998, following the success of “Titanic,” DiCaprio took on the challenge of playing dual characters in
“The Man in the Iron Mask,”
a historical drama involving four musketeers loyal to King Louis XIV. The film highlighted DiCaprio’s range by having him portray both the imprisoned twin and the king himself. Despite mixed reviews, the film succeeded commercially, bolstered by its star-studded cast and lavish production values, confirming DiCaprio’s ability to carry large-scale historical dramas.
A Minor Role in Woody Allen’s “Celebrity”
Also in 1998, DiCaprio appeared in “Celebrity,” directed by Woody Allen, who explored the pitfalls of fame through the experiences of writer Lee Simon, played by Kenneth Branagh. Though DiCaprio’s part was relatively limited, sharing the screen with notable actors like Judy Davis contributed to his growing portfolio. The film itself underperformed at the box office, receiving little attention, but it reflected DiCaprio’s appeal to a wide variety of cinematic styles early in his career.
Facing Addiction in “The Basketball Diaries”
In 1995, DiCaprio portrayed Jim Carroll, a high school basketball star grappling with drug addiction in “The Basketball Diaries.” The film focused less on sports and more on the personal and societal struggles of youth, addiction, and despair. As Jim’s life spiraled due to mounting pressures, DiCaprio’s gripping depiction of vulnerability and eventual hope cemented the film as a serious drama addressing the challenges of adolescence.
Family Challenges in “Marvin’s Room”
“Marvin’s Room” (1996) centered on two estranged sisters, Bessie and Lee, played by Diane Keaton and Meryl Streep respectively, who reunite after Bessie’s cancer diagnosis. DiCaprio appeared as Hank, Bessie’s troubled son, caught in the midst of family estrangement and reconciliation. The emotionally charged narrative explored themes of forgiveness, illness, and the complexity of family bonds. Robert De Niro’s role as Bessie’s doctor added further depth to this intense familial drama.
Modernizing a Classic: “Romeo + Juliet” in a Contemporary Setting
Director Baz Luhrmann’s 1996 reinvention of Shakespeare’s “Romeo and Juliet” placed the iconic love story in a fictional 1990s California city called Verona Beach. DiCaprio’s Romeo and Claire Danes’ Juliet spoke Shakespearean dialogue amid a setting defined by crime and corruption between rival mafia families. This fresh and imaginative retelling stood out for its bold visual style and youthful energy, underscoring DiCaprio’s growing ability to carry iconic, dramatic roles imbued with romantic intensity.
DiCaprio’s Breakthrough in “What’s Eating Gilbert Grape”
In 1993, DiCaprio earned his first Oscar nomination for his role as Arnie, a mentally disabled brother cared for by his older sibling Gilbert, played by Johnny Depp. The film delicately addressed themes of family responsibility, medical challenges, and perseverance within a small town environment. Despite not winning the Academy Award, this role launched DiCaprio’s reputation as a serious actor capable of empathizing with complex characters. Over two decades later, his Oscar win for “The Revenant” in 2016 finally garnered the recognition many believed he deserved.
Leonardo DiCaprio’s 1990s filmography exemplifies a journey marked by persistence and artistic growth, beginning with low-profile projects and culminating in iconic, award-nominated performances. These movies collectively reveal his willingness to embrace diverse and demanding roles, shaping him into one of Hollywood’s most respected actors. As his career moved beyond the decade, the foundation built by these films continued to influence his choice of parts and dedication to challenging storytelling.