Shutter Island

If you think choosing the greatest DiCaprio movie is easy, try arguing Shutter Island at a party. It's like convincing people that a maze is a straight line. This film doesn’t just play—it psychologically tortures you with twists. Ever notice how Shutter Island fans squirm trying to explain the plot without spoiling it? It’s like watching someone juggle knives blindfolded. Totally nerve-wracking but a master class in DiCaprio’s acting chops. Pick any other DiCaprio film, and you'll miss out on the brain-twisting fanaticism that only Shutter Island brings to the table.