Every Leonardo DiCaprio Movie Ranked Worst To Best

Exploring the career of one of our finest stars.

Leonardo DiCaprio Shutter Island
Warner Bros.

Leonardo DiCaprio's defining trait as an actor is also his most subtle. Since entering Hollywood at 19, his place as one of our finest stars has been underpinned by an uncanny ability to defy expectations and push himself to try new things with every role. He hides in every film, unpredictable and always fascinating to watch.

Proof of this chameleonic ability to shift between genre and challenge can be found in the fact that, over the last 30 years, DiCaprio has only appeared in 28 feature films (excluding two early and mercifully forgotten cameos in Critters 3 and Poison Ivy), a surprisingly low number given his fame and influence.

Picking his roles very carefully, DiCaprio has worked with such filmmakers as Martin Scorsese (with whom he's made six films and is working on a seventh), Steven Spielberg, James Cameron, Sam Mendes, Quentin Tarantino, and Christopher Nolan, and has been more consistent than many of his contemporaries in the process.

With that in mind, from his early work as a romantic lead to his seminal dramas and riotous comedies, here are all 28 Leonardo DiCaprio movies ranked worst to best.

28. Don's Plum (2001)

Leonardo DiCaprio Shutter Island
Polo Pictures

The hard truth of R.D. Robb's trite indie drama Don's Plum is that the backstory of its late release - that both DiCaprio and Tobey Maguire sued to keep it from being seen - would have made for a far more compelling movie than the film itself.

Concerned with a group of young friends who meet up to discuss life one night in a local diner, the film is a dismal tapestry of groan-inducing clichés and painfully thin characters, all of whom are portrayed by lifeless up-and-comers (including Ethan Suplee, Amber Benson, and Kevin Connolly) given nothing to work with.

Even here, you get the sense that DiCaprio is at least trying - futile as it may be - but between the tired script, pretentious execution and unoriginal melodrama, it's little wonder no one wanted anything to do with Don's Plum once it was filmed.

Contributor
Contributor

I get to write about what I love, so that's pretty cool. Be excellent to each other.