Top 5 Of The Most Romantic Leonardo Dicaprio Movies To Watch

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.

Photo: 20th Century Fox/Paramount Pictures

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.

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.

Photo: 20th Century Fox

The Man in the Iron Mask (1998)

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.


Photo: United Artists

Inception (2010)

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).


Photo: Warner Bros

The Great Gatsby (2013)

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.


Photo Credit: Warner Bros

Romeo + Juliet (1996)

Leonardo Dicaprio and Claire Danes portray the famous star-crossed lovers in this unique and original adaptation of Shakespeare’s play.


Photo: 20th Century Fox

Titanic (1997)

This epic star-crossed romance catapulted Leonardo Dicaprio and Kate Winslet into superstar status and they haven’t come down since.


Photo: 20th Century Fox/Paramount Pictures


Photo: Paramount Vantage/Dreamworks