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Leonardo DiCaprio: 40 Years in the Spotlight

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Photo: Leonardo DiCaprio, Source: GettyImages
Photo: Leonardo DiCaprio, Source: GettyImages

On 11 November, one of Hollywood’s most sought-after and highest-paid actors, Leonardo DiCaprio, celebrated his 50th birthday. A recipient of awards from the Screen Actors Guild, the Oscars, BAFTA, and the Golden Globes, DiCaprio has sustained a career spanning nearly 40 years, and remains at the peak of his craft. DiCaprio was listed among "The 50 Most Beautiful People in the World" by People magazine at the end of the last century, an accolade that continues to reflect his longstanding influence.

A private celebration marking the Titanic star's milestone was held at an estate in Hollywood Hills, drawing Hollywood’s elite, including longtime collaborator Robert De Niro, director Steven Spielberg, Brad Pitt, Katy Perry, Orlando Bloom, Paris Hilton, and many others. According to tabloids, few images from the event surfaced, as the San Vicente Bungalows, the Hollywood members-only club organising the occasion, implemented extensive privacy measures to protect both DiCaprio and his guests.

DiCaprio’s acting career began in the late 1980s. Before landing his first significant roles, he appeared in commercials and had minor parts in series like The New Lassie and Santa Barbara. His film debut came with the horror comedy Critters 3, and later that year, he starred in This Boy’s Life alongside Robert De Niro and Ellen Barkin. In 1993, DiCaprio starred with Johnny Depp in Lasse Hallström’s drama What’s Eating Gilbert Grape, earning his first Oscar and Golden Globe nominations for Best Supporting Actor.

Following that, DiCaprio’s career skyrocketed with roles in The Quick and the Dead, as poet Arthur Rimbaud in Total Eclipse, and in the sports drama The Basketball Diaries. Yet it was his portrayal of Romeo Montague in Baz Luhrmann’s musical Romeo + Juliet that cemented his star status, winning him the Silver Bear at the 47th Berlin Film Festival.

Undoubtedly, the major turning point for DiCaprio came with James Cameron’s Titanic. Initially hesitant to accept the role, he was eventually persuaded by Cameron, and it proved to be a career-defining decision. Although critics failed to fully recognise his contribution (the film earned 11 Oscar nominations but not one for Best Actor), his performance secured his place in the exclusive Hollywood "Club 20" — a nickname for actors commanding salaries of $15–20 million or more per film.

A notable Hollywood bachelor, DiCaprio has also been vocal in his support of Ukraine following Russia’s full-scale invasion. In February 2023, he donated generously to the Olena Zelenska Foundation to assist Ukrainian children affected by the conflict. DiCaprio shared on Instagram: 

"It is an honour to support the Olena Zelenska Foundation, which provides food and shelter to children and families in Ukraine."

As of today, DiCaprio’s filmography includes 47 titles, with four more in the works, including the crime drama The Battle of Bacton Cross, directed by Paul Thomas Anderson and featuring a stellar cast of Sean Penn, Benicio del Toro, Regina Hall, and others. Rumour has it that DiCaprio may also play Frank Sinatra in an upcoming Martin Scorsese film.

The Gaze invites you to revisit some of DiCaprio's most compelling past roles.

The Departed, 2006


This Martin Scorsese film is a remake of the 2002 Hong Kong film Infernal Affairs, based on the real-life Boston gang, Winter Hill. Set in and around Boston, particularly South Boston, the film follows Irish mob boss Frank Costello (Nicholson), who plants Colin Sullivan (Damon) as a spy within the Massachusetts State Police, while the police assign State Trooper Billy Costigan (DiCaprio) to infiltrate Costello’s gang. Both Sullivan and Costigan race to discover each other's identities before their own covers are blown.

Django Unchained, 2012


In Quentin Tarantino’s 2012 Western inspired by the classic spaghetti western Django, DiCaprio plays the brutal yet charming slave owner Calvin Candie. Alongside DiCaprio’s stellar performance, Jamie Foxx, Christoph Waltz, Kerry Washington, and Samuel L. Jackson shine in this satirical, dialogue-rich film. Jackson’s portrayal of the scheming, malevolent slave butler adds even more intrigue to this striking narrative.

The Revenant, 2015


DiCaprio finally won his first Oscar for Best Actor in Alejandro González Iñárritu’s survival thriller based on Michael Punke’s novel. The story follows Hugh Glass, a frontiersman on a quest for survival and vengeance. After his team suffers heavy losses due to hostile Native Americans, the unforgiving wilderness, and internal strife, Glass, left for dead, endures the brutal elements to seek revenge for his son’s murder. Tom Hardy, as the ruthless and racist antagonist, makes for an unforgettable counterpart to DiCaprio’s intense performance.

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