Even Leonardo DiCaprio has regrets. Yes, DiCaprio has spent his career choosing projects that turned him into one of Hollywood’s most bankable stars. He has rarely missed a step. But even DiCaprio has a “one that got away.”
Back in the 1990s, at the very moment his career was about to explode, he said no to a role that later became legendary. And while that decision cleared the path for his biggest break yet, ‘Titanic‘, it’s also the choice he now calls his greatest regret.
Leonardo DiCaprio’s Biggest Regret: The Role He Let Slip Away
By the mid-1990s, Leonardo DiCaprio was on fire. His breakout in ‘What’s Eating Gilbert Grape‘ earned him an Oscar nomination at 19. Then came ‘Romeo + Juliet‘, which made him a pin-up for millions of teens worldwide. In the eyes of Hollywood, he was the next big thing.
Related: 15 Best Leonardo DiCaprio Movies, Ranked
That’s when a young director named Paul Thomas Anderson came calling. Anderson had just made his first film, ‘Hard Eight,’ and was developing a bold, risky drama set in the world of the 1970s adult film industry. The movie was ‘Boogie Nights‘, and Anderson wanted DiCaprio to play its lead, Dirk Diggler. For DiCaprio, it would have been a chance to shake off the teen-idol label, but he said no.
The timing wasn’t on his side. James Cameron was simultaneously casting for ‘Titanic‘, a massive production already infamous for its ballooning budget. So, he had to make a choice. Talking to Esquire, he confessed, “My biggest regret is not doing Boogie Nights. When I finally got to see that movie, I just thought it was a masterpiece.” But confessions don’t wash the sting of regret, right?
The ‘Titanic’ Gamble
Choosing Titanic was one of the riskiest bets Leonardo DiCaprio took back then. Its budget was spiralling toward a (then-unheard-of) $200 million, production delays were making headlines, and insiders were whispering about the possibility of a box office disaster. Even though he hesitated to play “yet another romantic lead”, the chance of working with Cameron finally won.
The rest, of course, is cinematic history where DiCaprio’s biggest regret turned into his biggest success. ‘Titanic‘ shattered box office records, grossing more than $2 billion worldwide, and made DiCaprio and Winslet international icons. Jack and Rose became one of Hollywood’s most memorable on-screen couples, and DiCaprio’s name became synonymous with global stardom.
In case you missed it: Top 25 Romantic Comedy Movies
It’s hard not to play the “what if” game and choose safety nets. Had DiCaprio chosen ‘Boogie Nights‘, the film might have been even more iconic, but it could also have delayed or even derailed his rise to global superstardom. Without ‘Titanic‘, would he have become the “Leo,” whose name alone could sell out theatres worldwide?
