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Top 5 of the Most Romantic Leonardo DiCaprio Movies to Watch

We've ranked five of the best Leonardo DiCaprio romance movies and where to stream them.

With the upcoming release of Leonardo DiCaprio’s new movie, Killers of the Flower Moon (his latest since Don’t Look Up), I thought it would be fun to revisit some of the best Leonardo DiCaprio romance movies.

leonardo dicaprio romance movies collage including Titanic

While Leo is 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 – mostly due to his undeniable talent.

So, to celebrate Leonardo’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 Leonardo DiCaprio romance movies may change at any time. This article was last updated in August 2023 to celebrate the upcoming release of his new Martin Scorcese film.


Leonardo DiCaprio and Carey Mulligan in The Great Gatsby
The Great Gatsby is one of the best Leonardo DiCaprio love movies. Credit: Warner Bros.

5. The Man in the Iron Mask (1998)

The Man in the Iron Mask promotional image
The Man in The Iron Mask is a fun Leonardo DiCaprio drama. 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 The Man in the Iron Mask, an 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 their lives to do it, but their star-crossed love can never be.

Where to Watch: Paramount+, Showtime, MGM+, and Shout TV. You can also rent/buy it 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: 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 by director Baz Luhrmann.

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, Romeo + Juliet 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 “I’m 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 Titanic. 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…

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Honestly, I wish there were more movies today epic enough to make me want to watch them 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: Stream on Netflix or rent/buy on digital and DVD.

Honorable Mentions of Leonardo DiCaprio Romantic Movies:

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.)

Coming Soon: Killers of the Flower Moon

The movie will be released in select theaters on October 6, 2023, and will receive wide release on October 20, 2023. The film will also stream soon after on Apple TV+.

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

Top 5 of the Most Romantic Leonardo DiCaprio Movies To Watch Pinterest image


By on July 29th, 2019

About Amber Topping

Amber works as a writer and digital publisher full-time and fell in love with stories and imagination at an early age. She has a Humanities and Film Degree from BYU, co-created The Silver Petticoat Review, contributed as a writer to various magazines, and has an MS in Publishing from Pace University, where she received the Publishing Award of Excellence and wrote her thesis on transmedia, Jane Austen, and the romance genre. Her ultimate dreams are publishing books, writing and producing movies, traveling around the world, and forming a creative village of talented storytellers trying to change the world through art.

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