With the recent release of Leonardo Dicaprio’s new movie, Once Upon a Time in Hollywood (his first movie in four years), I thought it would be fun to revisit some of the most romantic Leonardo Dicaprio movies. While Leo’s recognized as one of the greatest actors in the world playing a variety of roles, let’s not forget his romantic leading man appeal! When he was a teen, young girls fell in love with his baby face, floppy blonde locks, and intense onscreen charisma. And he hasn’t lost his appeal since.

So, to celebrate Leo’s still-appealing leading man status, here’s a ranking of Leonardo Dicaprio’s most romantic movies based on swoony-worthy appeal.

Note: Availability of these movies may change at any time and was researched at the time of publication.

Romantic Leonardo Dicaprio Movies, Ranked (Spoilers Included)

(In Descending Order)


5. The Man in the Iron Mask (1998)

The Man in the Iron Mask promotional image
Photo: United Artists

How it’s Romantic: Leonardo Dicaprio plays twin roles in this romantic period adventure film. One, the evil King Louis, and the other his sweet and secret twin brother, Phillipe. And while the handsome evil King Louis romances a young French woman, it’s not Leo making this film romantic and swoon-worthy. Rather it’s the subtle love story of Queen Anne and D’artagnan that will steal your heart. Still, Leonardo shines in this imperfect but entertaining period drama. He should act in romantic period dramas more often.

I think that it is possible for a man to love one woman all his life and be the better for it.

D’artagnan in The Man in the iron mask

Most Swoon-Worthy Moment: Queen Anne and D’artagnan share a passionate kiss, even risking death to do it, but their star-crossed love can never be.

Where to Watch: STARZ, STARZ Amazon channel, rent/buy on digital and DVD.

4. Inception (2010)

Leonardo Dicaprio kisses Marion Cotillard's head in Inception. Top 5 of the Most Romantic Leonardo Dicaprio Movies to Watch
Photo: Warner Bros

How it’s Romantic: Leo plays Dom Cobb, a man stealing corporate secrets through dream-sharing technology. He also happens to be a haunted widower still in love with his deceased wife Mal (Marion Cotillard). They’re together in his dreams but soon everything begins to fall apart when reality replaces fantasy. While Leo as the brooding, romantic leading man is swoon-worthy, this romance is doomed from the start.

In my dreams we are together.

Dom Cobb in Inception

Most Swoon-Worthy Moment: Dom tells Mal how they grew old together.

Where to Watch: Max Go, Cinemax on Amazon Channel, rent/buy on digital and DVD.

3. The Great Gatsby (2013)

Movie: The Great Gatsby photo. Top 5 of the Most Romantic Leonardo Dicaprio Movies to Watch
The Great Gatsby. Photo Credit: Warner Bros

How it’s Romantic: Leonardo Dicaprio in a classic literary romance adaptation? YES! Leo gleams with romantic appeal in the stylized adaptation of the wealthy and enigmatic Jay Gatsby. While he woos and professes his love to the self-obsessed Daisy, tragedy beckons on the horizon. Still, while Leo excels as the romantic leading man in this film, it’s hard to root for the actual love story since it’s more one-sided and verges on the obsessive.

I knew that when I kissed this girl, I would be forever wed to her.

Jay Gatsby in The Great Gatsby

Most Swoon-Worthy Moment: Gatsby comes in out of the rain and reunites with Daisy after years of separation.

Where to Watch: Rent/buy on digital and DVD.

2. Romeo + Juliet (1996)

Romeo + Juliet promotional image. Top 5 of the Most Romantic Leonardo Dicaprio Movies to Watch
Photo: 20th Century Fox

How it’s Romantic: Leonardo Dicaprio and Claire Danes portray the famous star-crossed lovers in this unique and original adaptation of Shakespeare’s play. Leo proved he had major heartthrob status and it’s hard not to swoon as Romeo gives romantic speeches and successfully wins over the heart of Juliet. In all, this is a fabulous love story staying faithful to Shakespeare while also appealing to contemporary audiences.

I defy you, stars!

Romeo in Romeo + Juliet

Most Swoon-Worthy Moment: Romeo and Juliet see each other through the fishbowl as Des’ree’s haunting melody “Kissing You,” plays.

Where to Watch: Rent/buy on digital and DVD.

1. Titanic (1997)

Kate Winslet and Leonardo Dicaprio in Titanic. Top 5 of the Most Romantic Leonardo Dicaprio Movies to Watch
Titanic. Photo: 20th Century Fox/Paramount Pictures

How it’s Romantic: As far as romantic Leonardo Dicaprio movies go, this one is undeniably the most swoon-worthy. This epic star-crossed romance catapulted Leonardo Dicaprio and Kate Winslet into superstar status and they haven’t come down since.

James Cameron did everything right with this film. From the elements of classic romance to the famous Titanic tragedy to the humor to the hopeful ending despite the heartbreak. This is a movie that makes you feel. And yes, I admit it; I may have been a young teen when this movie first premiered but I saw it seven times in the theater. No regrets…Honestly, I wish there were more movies today epic enough to make me want to watch again and again.

All these years later, when it’s on TV or if I feel like an escape, this is still one of my top go-to choices to watch.

Most Swoon-Worthy Moment: While the kiss at the bow of the ship is iconic, the most swoon-worthy romantic moment happens after the iceberg collision. As the ship sinks, Rose and Jack hold onto each other at the stern of the ship. They know they’re probably going to die but Rose finds the positive. “Jack, this is where we first met!” He then kisses her on the forehead as they brace for impact.

Where to Watch: Rent/buy on digital and DVD.

Honorable Mentions:

Revolutionary Road photo
Revolutionary Road. Photo: Paramount Vantage/Dreamworks
  • The Aviator (The romance between Leo’s Howard Hughes and Cate Blanchett’s Katharine Hepburn is compelling.)
  • Revolutionary Road (Leonardo Dicaprio and Kate Winslet prove they still have amazing chemistry. That said, this movie is depressing and difficult to watch.)
  • Catch Me if You Can (There’s a cute romance with Amy Adams.)
  • Blood Diamond (The romantic tension between Leonardo and Jennifer Connelly is palpable.)
  • Gangs of New York (Onscreen romance with Cameron Diaz though the movie’s too violent for my taste.)

What are your favorite romantic Leonardo Dicaprio movies? Did I leave your favorite off the list? Let me know in the comments!


Featured image credit: 20th Century Fox/Paramount Pictures, Warner Bros

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Promotional image of The Man in the Iron Mask.

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