As one of the biggest stars in the business, Leonardo DiCaprio has earned the right to pick and choose his projects carefully. He’s developed an impressive habit of not only being selective but lending his immense talents to projects almost guaranteed to succeed.

To illuminate that point, consider that his last five features have been The Wolf of Wall Street, The Revenant, Once Upon a Time in Hollywood, Don’t Look Up, and Killers of the Flower Moon. Of those five, he was nominated three times for ‘Best Actor’ at the Academy Awards and finally took home the big one in the process.

The quintet also netted him two Golden Globes after he was shortlisted for all five performances, and in total, his most recent big-screen outings were in the running for a combined total of 41 Oscars – an average of over eight per film – even if they only won five all told. Still, that shows just how carefully DiCaprio curates his next career move, even if everybody has one movie that will be deemed the worst of the worst.

It would be far too easy to point the finger of blame in that regard at 1991’s straight-to-video horror sequel Critters 3, but that wouldn’t really be fair when it was his first-ever role, and he was only a teenager at the time. Instead, the burden deserves to be placed upon Danny Boyle’s turgid adaptation of The Beach because, apart from some stunning cinematography, it’s an exhausting bore that aims for the melancholic but flirts with the pretentious instead.

Boyle reuniting with Trainspotting scribe John Hodges for another literary adaptation was enough to generate plenty of anticipation, never mind the fact DiCaprio’s star was still riding the momentum from James Cameron’s Titanic when production began in 1999. All of the pieces were there for a riveting adventure with lashings of existentialism, but in the end, there was only tedium to be found.

The leading man’s intrepid backpacker, Richard, pitches up in Thailand dreaming of a life-changing experience, where he becomes entranced by the mere mention of a near-mythical beach. Joining an isolated community upon their arrival, where tensions of a physical, psychological, and sexual nature soon arise to turn his ideas of paradise into an increasing nightmare.

For the first – and still only – time in his career, DiCaprio received the unwanted distinction of being in the running for the Golden Raspberry Awards’ ‘Worst Actor’ trophy. While he wasn’t objectively terrible performance-wise, even his radiant star power is dimmed significantly by an overindulgent pontification of what paradise really means. It was Boyle’s maiden attempt at a mass-produced Hollywood movie with a decent budget, and it shows because any identifiable style or urgency is swept up in a sea of blandness.

What should have been a riveting dramatic thriller that existed somewhere between The Lord of the Flies and Apocalypse Now instead became bogged down in philosophical mundanity, heavy-handed metaphors, narrative inertia, and grandiose self-importance. There’s a great story in there, as Alex Garland’s source novel displayed. Unfortunately, Boyle never comes close to capturing the essence of The Beach, with DiCaprio left to flounder as little more than eye candy without the platform to sink his teeth into a memorable or even multi-dimensional character.

It still made almost $150million at the box office, though, which may have had a lot to do with the DiCaprio-obsessed Titanic demographic being suitably won over by the trailers that relied on him parading around shirtless. Again, it’s not an atrocious work of cinema, but for somebody with a filmography as esteemed as Leo’s, it’s the lowest point yet.