Countless jokes later, Leonardo DiCaprio finally did it: he won an Academy Award. It only took six nominations in 23 years. DiCaprio won best actor for his movie The Revenant. In light of his newest win, it’s only necessary to go back and relive the DiCaprio days. All of the tear-jerking, ridiculously funny, and straight-up silly movies that made DiCaprio a man that millions pined over and made jokes of since that first nomination have all lead up to this moment.
27 years ago the world was introduced to Leonardo DiCaprio on a show called The New Lassie. He played a young boy named Glen who starred in only four episodes of the show. The New Lassie preceded other shows like The Outsiders, Roseanne, Santa Barbara, and Parenthood in which DiCaprio played only minor roles, his biggest one being 12 episodes in Parenthood.
Come 1993 DiCaprio starred in a film titled This Boy’s Life, where he acted opposite Robert De Niro. This was not his first actual film (his first was Creepers 3) but it was his first well-known film and definitely provided for DiCaprio’s future career.
Between 1993 and 1996 DiCaprio starred in six films. but in 1996, he scored a role as Romeo in – you guessed it – Romeo + Juliet. This was a wild, modern interpretation of Shakespeare’s play of the same name that emphasized violence within gangs and racism. This was far more popular than This Boy’s Life and was an instrumental point that helped him land his next film.
1997 was possibly a bigger year for Leonardo DiCaprio than 1996 was. It was this year approximately 17 years ago that DiCaprio got cast as Jack Dawson in the tragedy of Titanic. Titanic was by far the most popular movie Leonardo DiCaprio had starred in throughout the entirety of the 90s. Titanic explored the new love between Jack Dawson and Rose Bukater (Kate Winslet) aboard the RMS Titanic. Titanic received a 69% audience must-see rating according to Rotten Tomatoes.
Although DiCaprio emerged in the 90s, the 2000s began a legacy of movies that are remembered to this day that starred and co-starred DiCaprio. He has been credited for a total of 16 productions between the years 2000 and 2012, some of which including Gangs of New York and Catch Me If You Can in 2002, The Aviator in 2004, and Django Unchained in 2012. It was by this time that DiCaprio had been nominated for three out of six of his Academy Award nominations, all of which he lost. One of the awards he was nominated for was best supporting actor in What’s Eating Gilbert Grape in 1993, while the other two award nominations were for best actor in The Aviator in 2005 and Blood Diamond in 2007.
In 2013, Leonardo DiCaprio starred in two more hit movies that both won 5+ awards; The Wolf of Wall Street and The Great Gatsby. Both of these movies were a turning point for DiCaprio’s career, being two of the most awarded movies of his career. That was until 2015.
DiCaprio won best actor for the first time thanks to his 2015 movie, The Revenant. This is the first Oscar he has won in his entire career for any of the films he has done.
Leonardo DiCaprio has been destined for greatness from playing little Glen on The New Lassie, Jack Dawson on the tragic Titanic, to Hugh Glass on The Revenant, and here’s to the many more films he will do in the future. Here’s to you, Leonardo DiCaprio, and to many more Oscars (hopefully you won’t have to wait too long!).
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