How different would Leonardo DiCaprio’s career have been if he made ‘Boogie Nights’ and ‘American Psycho’ instead of ‘Titanic’?

In 1997, Leonardo DiCaprio‘s transformation from teen heartthrob into, well, an even bigger teen heartthrob was completed by the release of James Cameron’s era-defining Titanic.

Before Cameron cast him in the biggest goddamn movie of all time, DiCaprio was already plastered on the walls of teen girls everywhere, thanks to his raw performance in Baz Luhrmann’s excellent 1996 version of Romeo + Juliet, which transported Shakespeare’s play to modern-day Verona Beach, California, out of all the fucking places to choose from. However, Titanic made the handsome, floppy-haired, youthful star go supernova, and within months, he was being offered $20million to star in the adaptation of a controversial 1991 novel by Bret Easton Ellis: American Psycho.

To say Hollywood was shocked that DiCaprio, with his cherubic looks and hordes of female fans, was considering playing a yuppie serial killer in a 1980s satire would be a gargantuan understatement. In May 1998, though, it was announced: DiCaprio was in, much to the chagrin of director Mary Harron, who was adamant his boyish good looks were wrong for the film, and that his teen fanbase wasn’t the right crowd for this material anyway. She also had an actor she was desperate to cast, but when the studio nixed the idea of the then-unknown Christian Bale, she walked off the project.

Following Harron’s departure, DiCaprio developed the project with Oliver Stone for a while. However, he eventually heeded the warnings of women’s liberation icon Gloria Steinem, who had always been an outspoken critic of Ellis’ novel. She believed starring in the film would send the wrong message to his fanbase, and she was probably fucking right, all things considered. In the end, Harron and Bale, who had simply bided their time and waited for DiCaprio to come to his senses, swooped in and made the modern classic satire we all know and love.

In truth, this awkward point in his career is one of the few times in which DiCaprio didn’t seem fully in control of who and what he wanted to be. A few years earlier, Paul Thomas Anderson had sent him the script for Boogie Nights, having been impressed with his performance in 1995’s The Basketball Diaries. DiCaprio read the script and loved it, but was then presented with a Sophie’s Choice situation: he could do Boogie Nights or Titanic, but not both.

Of course, he chose to become the king of the world, and recommended his Basketball Diaries co-star Mark Wahlberg to Anderson for the role of Eddie Adams/Dirk Diggler. In later years, though, he called turning down Boogie Nights his greatest career regret, despite it being extremely hard to imagine DiCaprio, who looked about 16 years old at that time, playing the well-endowed porn star at the centre of Anderson’s Scorsese-esque rags-to-riches tale.

Unfortunately for DiCaprio, having let two future classics slip through his fingers (which, admittedly, mightn’t have been suitable for him anyway), the movies he chose to make instead account for a few of the only misfires on his CV. The Man in the Iron Mask, Woody Allen’s Celebrity, and Danny Boyle’s The Beach aren’t exactly a trifecta anyone would want to celebrate, and after The Beach‘s disappointing reception, the confused young star disappeared from the spotlight for a couple of years to reassess his burgeoning career.

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