
The 1997 career crossroads that left Leonardo DiCaprio “convinced he’d made a terrible mistake”
Leonardo DiCaprio is undoubtedly the most successful movie star of his generation, and not necessarily because his films have raked in the most profit, but even he was unable to anticipate his greatest success.
An actor who is associated with prestige, DiCaprio has worked with nearly every great living director and starred in three films that have won the Academy Award for ‘Best Picture’. Every single DiCaprio film is considered an ‘event’, and even his less successful endeavours are worthy of discussion. While Daniel Day-Lewis might have the more perfect track record, DiCaprio’s films have been consistent box office successes, which is all the more impressive given that he’s never been involved in a franchise or done a superhero role.
DiCaprio may have had a family that was involved in the entertainment industry, but they didn’t have enough success for him to be considered a ‘nepo baby’. In fact, his brother Adam was the first to be interested in acting, and said that this attracted a young DiCaprio’s attention: “Leo saw what I was doing and that’s what got him interested in acting,” his brother said, “He hated school and when he saw I was making good money and you could be schooled on set, he asked if he could do it too.”
According to Adam, DiCaprio’s interest in acting only intensified when he began growing up, as he added, “Leo started acting when he was about nine or ten, starting with a Matchbox toy car commercial, which led to other jobs. Though he wasn’t an overnight success, he stuck with it because the alternative was homework. As a child actor, he only had to study a couple of hours a day on set.”
DiCaprio had the benefit of getting his work seen by the right people; his breakout performance in Growing Pains attracted the interest of Robert De Niro, who selected him to play his son in the social drama A Boy’s Life. It was shortly after that that his performance in the drama What’s Eating Gilbert Grape earned him an Academy Award nomination for ‘Best Supporting Actor’.
While Titanic is now known as one of the biggest successes in the history of cinema, there were many who doubted James Cameron’s vision because of the famously tumultuous production, and Adam said that this caused doubts to seep into his brother’s mind.
“Leo was actually convinced he’d made a terrible mistake with Titanic,” he recalled, “He was convinced it was going to be a flop. Then he became the biggest star in the world”.
The success of Titanic almost can’t be quantified in comparison to any modern film; not only was it a number one box office hit for months on end, but it encapsulated the cultural moment and became the most dominant thing in the world. In the days before prestige television had taken off, a hit film felt like a monocultural event. DiCaprio turned into an instant star and was offered a number of opportunities, and was placed in the spotlight in a way that he had never anticipated before.
The irony is that Titanic was never one of DiCaprio’s greatest performances, as praise for the film tended to gravitate towards Cameron and Kate Winslet. It was arguably once he began collaborating with Martin Scorsese that he developed the reputation for being a ‘serious actor’.


