‘Growing Pains’: The Career Evolution of Leonardo DiCaprio

In recent years, Leonardo DiCaprio‘s career has taken on a life of it’s own. Fans are obsessed with Leo’s Academy Award chances (probably even more than the actor himself). Dame Maggie Smith has endorsed Leo and one group of fans even created an arcade style video game based on his career. In anticipation of yet another possible Oscar loss, we thought we’d look back at Leo’s best and worst moments.


Early Career (1989 - 1992)
Leonardo DiCaprio, Growing Pains
DiCaprio's now famous career got off to an inauspicious start. When he was just five years old, Leo was kicked off the set of a show called Romper Room for being disruptive. DiCaprio went on to star in Critters 3, Roseanne, Growing Pains, and a Matchbox commercial. However, it wasn't all smooth sailing for the future teen heartthrob. "He was kind of a dork," recalled one classmate, "like a little wimpy guy."
Notable Roles: Critters 3, Growing Pains
Breaking In (1993 - 1995)
Leonardo DiCaprio, What's Eating Gilbert Grape
No single film epitomizes Leo's career more than What's Eating Gilbert Grape. In 1993, DiCaprio appeared alongside Johnny Depp which earned him the first of his many Oscar snubs. Director Lasse Hallström was originally looking for a less attractive star, but was blown away by Leo's audition claiming he was the "most observant" actor.
Notable Roles: What's Eating Gilbert Grape, The Basketball Diaries
Teen Heartthrob (1996 - 2001)
Leonardo DiCaprio, Titanic
In the late '90s, Leonardo DiCaprio's fame approached Beatle-esque heights. DiCaprio's Romeo + Juliet costar Claire Danes described him as "very aesthetically pleasing," which honestly sounds like something a robot posing as a human being would say. During Titanic's premiere at the Tokyo Film Festival, a police force was needed to maintain order. Thousands of hysterical DiCaprio fans surrounded the theater with one girl even claiming "Leo, I'm ready to die for you!"
Notable Roles: Titanic, Romeo + Juliet, The Man in the Iron Mask, The Beach
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Oscar Contender (2002 - 2007)
Leonardo DiCaprio, Gangs Of New York
This period is the most critically acclaimed era of DiCaprio's career, earning Oscar nominations for his roles in The Aviator and Blood Diamond. Leo also formed a close partnership with director Martin Scorsese, starring in films like The AviatorThe Departed, and Gangs of New York
Notable Roles: Blood Diamond, The Departed, The Aviator, Catch Me If You Can, Gangs of New York
Blockbuster Success (2008 - 2011)
Leonardo DiCaprio, Revolutionary Road
In 2010, Leo starred in Inception, a movie that was so well loved, it makes you wonder whether or not someone implanted the idea that it was a good movie into everyone's mind. The film grossed over $825 million, the second-highest total of DiCaprio's career. For his role in the movie, Leo was paid a percentage of ticket sales. This paid off (literally) and DiCaprio earned the highest payday of his career: $50 million.
Notable Roles: Inception, Shutter Island, Revolutionary Road, Body of LiesJ. Edgar
Renaissance (2012 - Present)
Leonardo DiCaprio, Django Unchained
Dan Jackman via WENN
In 2013, DiCaprio teamed up with Scorsese for the fifth time in The Wolf of Wall Street. Leo's performance as Jordan Belfort earned him his fourth and fifth Academy Award nominations and his fourth and fifth Academy Award losses. In 2016, DiCaprio was nominated for his sixth Oscar for his role in Alejandro González Iñárritu's The Revenant. In an effort to finally win an Oscar, Leo acted the shit out of the movie; he learned to shoot a musket and speak two languages and ate raw bison liver.
Notable Roles: The Revenant, The Wolf of Wall Street, The Great Gatsby, Django Unchained