From Teen Idol to Gatsby: Leonardo DiCaprio’s 20 Years Of Films [Flashback]

Favorite DiCaprio Quotes
10 of our favorite quotes from Mr. Dicaprio
Leonardo DiCaprio was only 19-years old when he garnered his first Academy Award nomination for the 1993 film What’s Eating Gilbert Grape. DiCaprio had only been in Hollywood a short time, but quickly proved himself to be incredibly talented and versatile with  his moving portrayal of the mentally challenged Arnie Grape. Shortly thereafter, Leo solidified his place as a dreamy teen idol with his blonde hair, blue eyes, and his convincing portrayals of the dreamy, love torn Romeo (Romeo + Juliet), and Jack Dawson (Titanic).

Now, at 38-years-old, DiCaprio continues to prove himself as a talented, good-looking, and bankable Hollywood entity with movies such as Blood DiamondInception, Django Unchained, and, most recently, The Great Gatsby

While promoting his newest film, an adaptation of F. Scott Fitzgerald’s 1920’s, American novel, The Great Gatsby, DiCaprio sat down with Extra to talk about the risks of making ‘The Great Gatsby’, his privacy, plans for starting a family, and taking a break from Hollywood.

Read more about the interview after the jump, and launch the gallery for a look at the 20+ films DiCaprio has starred.

Of his newest film, The Great Gatsby, DiCaprio admits “it’s a risk” to take such a celebrated American novel and make it into film, “you’re almost setting yourself up for criticism in a lot of ways.” That kind of risk does not scare DiCaprio, who after twenty years has adapted to the pressures and challenges of being an actor.

Even the prying eyes of the media do not seem to phase him. Having spent the last 2 decades as an A-lister in Hollywood, DiCaprio’s private life (with Gisele BundchenBar Refaeli, and Blake Lively) has been well documented in tabloids. In his interview, DiCaprio recognizes that he has had to sacrifice privacy in this career. However, he explains that he has adapted to the circumstances of being a leading man in Hollywood and understands there is a “certain price for everything we do.” Regardless, he still considers himself a lucky person and notes, “I have absolutely nothing to complain about.”

Although he is not complaining about the chaotic life, DiCaprio did confess a desire to take a break from making films for “a few months” to pursue his other passions, particularly environmental activism.

As for whether or not he will be leaving bachelorhood for parenthood? Although DiCaprio was quoted in a 2008 interview with Parade stating “I want to get married and have children;” today, DiCaprio is not answering that question as confidently. He explained to Extra that he does not try to determine the future, but rather “takes it day by day.”

See more of Leonardo DiCaprio in the gallery, and let us know what your favorite Leonardo DiCaprio movie is.