Despite the fact that Leonardo DiCaprio has been one of the biggest movie stars for two decades and has grown up in front of the cameras, he still has an unknown quality.

DiCaprio, like many other actors before him, has spent much of his career attempting to upend our expectations of him — from matinee idol to grim poet to tortured soul and back again — before settling into his comfort zone as perhaps the most interesting, ambitious A-lister currently working in the last decade.

He’s collaborated with Martin Scorsese five times, as well as Steven Spielberg, Quentin Tarantino, Christopher Nolan, Baz Luhrmann, Clint Eastwood, Danny Boyle, and Woody Allen.

DiCaprio’s portrayal is, in many ways, the essence of Quentin Tarantino’s bold, ambitious, and often somewhat tragic homage to a vanished period of Los Angeles. In many ways, DiCaprio’s performance is the soul of Quentin Tarantino’s audacious, ambitious film.

Brad Pitt (justifiably) won the Oscar for Once Upon a Time in Hollywood, but in many ways, it’s DiCaprio’s performance that is the soul of Quentin Tarantino’s audacious, ambitious film, and also quite sad ode to Four of Leo’s top five films are Martin Scorsese productions, as you may have observed.

These are four very different performances, but they’re all fantastic in their own right, and they’re all the clearest representation of DiCaprio’s tremendous skill set as the Wolf of Wall Street. Inception is Leonardo DiCaprio’s biggest smash since Titanic, and it’s the first true event film he’s been a part of since James Cameron’s blockbuster. “Good lord, look how young Leo and Kate are,” you would think if you’ve lately seen Titanic.