The 5 Most Inspiring Leonardo DiCaprio Movies of All Time

Since dropping onto the scene over thirty years ago in the 80’s sitcom Growing Pains, Leonardo DiCaprio has had a wild and incredibly diverse acting career.

Since then, he’s built up quite the resume, from Romeo in the cult hit Romeo+Juliet, Howard Hughes in The Aviator, Calvin Candie in Django Unchained, and Jay Gatsby in The Great Gatsby to name a few.

Sometimes, DiCaprio’s work is vicious and unforgiving, such as when he played Hugh Glass in The Revenant or Billy in The Departed (the latter of which probably has one of the best endings in cinematic history).

But other times, it’s inspiring and eye-opening. Sometimes, it’s the kind of film and a role that reminds you of the power of some aspect of humanity. Other times, it opens your eyes to the possibilities, however fictional, that make you believe in a weird way that more is possible in your own life.

If you can do what you do best and be happy, you're further along in life than most people.

– Leonardo DiCaprio

These are five of the most inspiring Leonardo DiCaprio movies of all times.

Titanic (1997)

James Cameron’sTitanic was DiCaprio’s first mega-hit. It was the movie that made him a household name and what essentially launched him to the A-list in Hollywood– where he’s since stayed.

It was also where he first met Kate Winslet, whose chemistry in Titanic helped make the movie what it was. It’s their love story, Leo as Jack and Winslet as Rose, that makes the film so memorable.

The film serves as one of the most powerful love stories ever told. It’s a reminder of how love pierces through all facades and breaks through barriers to the heart of things.

The Aviator (2004)

The first of two Martin Scorsese films on this list (they like each other, clearly– see: The Departed), The Aviator tells the life of the eccentric tycoon Howard Hughes.

The film has glamour, conflict, tension, and about everything you’d expect from a Hollywood magnate. However, it also tells the painfully personal story of Hughes’ wrestle with OCD and legal troubles.

It’s not your classic “happy ending”, however, the film has more than its fair share of motivating themes that leave you both energized and reflective.

Inception (2010)

Christopher Nolan’s Inception was a big budget film that had huge expectations placed on it from the very beginning.

Somehow, amidst the incredibly layered plot and mind-bending special effects, Leo stood out as a memorable part of Inception’s complex story.

It’s not the kind of film that’s generally considered inspiring in the typical way. However, Inception makes you rethink the possibilities inherent in reality itself.

The things that are capable in the movie make you believe that anything might be possible through the mind in this life. And, in an odd way, every time I’ve watched the film that thought has left me feeling excited and inspired to do my own work.

The Wolf of Wall Street (2013)

Martin Scorcese’s The Wolf of Wall Street isn’t all good and inspiring.

I was careful to include it on the list because it involves a story about crime and ultimately losing control of one’s power.

However, the story also tells of someone– Jordan Belfort (DiCaprio)– coming up from nothing and building an empire in an incredible fashion, even if things eventually go awry.

Ultimately, it’s a cautionary tale but also a damn inspiring one that everyone should watch.

The Basketball Diaries (1995)

Probably the most purely inspirational movie on this list (and the one you’re most likely to never have heard of), The Basketball Diaries was one of several movies DiCaprio starred in before his break in Titanic.

It tells the story of a young Jim Carroll (DiCaprio) who goes from neighborhood basketball star to heroin drug addict. After hitting rock bottom he finds help– and redemption– through friends and strangers alike.