Here’s To Lookin’ At Some Of The Most Swoon-Worthy Romance Films In History

From epic “Here’s to lookin’ at you kid” one-liners to a legendary boom box serenade, silver screen romances have evolved through the years. Even if modern-day romances aren’t considered as swoon-worthy as they were during the Golden Age of Hollywood, they still play their part in the evolution of the romance genre.

No matter if it’s Humphrey Bogart, Leonardo Dicaprio, or John Cusack, once the end credits start to roll, people are left smitten, glowing, and on a mission to find an epic love of their own. Get ready, because here’s to lookin’ at some of the most swoon-worthy romance films in cinematic history.

Gone With The Wind

Gone With The Wind
Warner Bros.
Warner Bros.

Set in the antebellum south of 1936, Gone With the Wind is a sweeping historical romance epic that has people swooning over the relationship of Scarlett O’Hara and Rhett Butler. While the tale starts off with O’Hara secretly in love with another man, she soon realizes her attraction to the cynical and charming Rhett.

Of course, that chemistry isn’t lost on the audience, as the two lead actors have undeniable chemistry on screen. With the will-they-won’t-they relationship between the two main characters, the Academy Award-winning movie proves that romance is a Golden Age of Hollywood specialty.

It Happened One Night

It Happened One Night
Columbia Pictures
Columbia Pictures

When the 1934 rom-com It Happened One Night wrapped up filming, star Claudette Colbert told her friend that she had just finished the worst picture ever. Ironically, the film wound up winning all five major categories at the Academy Awards, one of three films to ever do so.

The film is credited for being the blueprint for all romantic comedies, with the snappy dialogue, electric chemistry, and familiar tropes. There’s Ellie, a headstrong heiress who’s trying to get out of her father’s influence. And then there’s Peter, a street-smart reporter who couldn’t be more opposite than the rich girl. Of course, they fall in love and balance each other out.

Casablanca

Casablanca
Warner Bros.
Warner Bros.

You really can’t get any more romantic than Humphrey Bogart’s Rick and Ingrid Bergman’s Ilsa. A wartime love story, Casablanca goes where many films of the romance genre are scared to venture — into the realm of an unhappy ending. The thing is, it makes this movie that much more swoon-worthy.

Sorry, but if you didn’t cry when Ilsa tries to stay behind with Rick and he doesn’t allow her, you need to reevaluate your emotions. Especially considering he tells her that she’d regret staying, “Maybe not today, maybe not tomorrow but soon and for the rest of your life.”

Moulin Rouge!

Moulin Rouge!
20th Century Fox
20th Century Fox

Lights, camera, swoon! Moulin Rouge! isn’t just a masterful romance film, it’s the movie that showcased Ewan McGregor’s musical talents. And, to be honest, it’s hard not to fall in love with the poet obsessed with love when he opens his mouth to sing.

Obviously, Nicole Kidman’s courtesan character Satine agrees with us because it doesn’t take long to fall for Christian. Their romance story is one of passion and heartbreak, leaving the audience yelling at the unfairness that occurs at the end of the film. If you don’t know what we’re talking about, you’re going to have to watch their tragic romance for yourself.

Love Affair

Love Affair
RKO Radio Pictures
RKO Radio Pictures

Weirdly enough, there was a time before Meg Ryan and Tom Hanks made plans to meet on top of the Empire State Building. And that time was in the 1939 film Love Affair. When Michel Marnet falls for singer Terry McKay on a cruise, sparks immediately fly. Unfortunately, they’re both engaged to someone else.

So, what do they o? They make plans to go back to their partners and then meet in six months on the observation deck on the Empire State Building. What makes this swoon-worthy is the fact that Terry is in an accident that might leave her paralyzed, and Michel says they’ll work through it together.

Brief Encounter

Brief Encounter
Eagle-Lion Distributors
Eagle-Lion Distributors

From the beginning of their chance encounter, the romance between Laura and Alec is raw and yet doomed. In the 1945 film Brief Encounter, viewers watch as bored housewife Laura meets general practitioner Alec at a railway station, who also so happens to be married with children.

Things start to get heated when the two keep accidentally running into one another, and, quickly, the two begin to fall for one another. Using a fellow doctor’s apartment as a meeting place, it seems like Alec will do anything for Laura. But, like Casablanca, there is no happy ending for these two, no matter how much the audience wishes it.

Romeo + Juliet

Romeo + Juliet
Twentieth Century Fox
Twentieth Century Fox

While it’s not the original Shakespearean play, the 1996 modern adaptation of Romeo + Juliet starring a young Leonardo DiCaprio and Claire Danes still brings tears to our eyes. The story is timeless, with two teenagers of feuding families falling in love despite their parents’ protests.

Of course, it’s a tragic ending, with the two teens believing the other dead. There’s just something about their forbidden romance that makes the tale one of the most epic romance stories around. The main theme of love is an overpowering force that has Romeo and Juliet deserting their loyalties in favor of one another.

His Girl Friday

His Girl Friday
Columbia Pictures
Columbia Pictures

In one of the best gender-swap romance stories, Howard Hawks’ rom-com His Girl Friday proves that sometimes a second chance is all a person needs. Starring Cary Grant and Rosalind Russell, the film follows the story of editor Walter Burns as he tries to keep his best reporter/ex-wife, Hildy Johnson, from leaving the newspaper and marrying another man.

Getting her to agree to take on one more case with him is his last shot at redemption. Only, the story is about murderer Earl Williams, and more than one surprise awaits the ex-couple. Honestly, with everything they go through, you can’t help but root for the mess of a couple.

Pride & Prejudice

Pride & Prejudice
Universal Studios
Universal Studios

One of the most epic love stories to date is that of Mr. Darcy and Elizabeth Bennet in Pride & Prejudice. Not only is the dialogue in Joe Wright’s film enough to bring the strongest person to their knees, but it’s the chemistry between Keira Knightly and Matthew MacFadyen that has sparks flying off the screen.

Of course, love is anything but simple when it comes to a Jane Austin narrative, and Mr. Darcy is hesitant to fall for Elizabeth even though there is undeniable chemistry between the two. Alas, Mr. Darcy will always represent the age of the romantic gentleman.

When Harry Met Sally

When Harry Met Sally
Columbia Pictures
Columbia Pictures

The 1989 romance film When Harry Met Sally raises a very serious question, “can men and women be platonic friends?” The answer is, of course, but not when it comes to this film! Meeting in a car going from Chicago to New York, Harry and Sally argue about that exact question, parting ways with no definite answer.

During a 12-year-long on-and-off-again friendship, Harry and Sally finally realize that their friendship never worked out because they’re meant to be together. The rom-com is the perfect example of viewers wanting nothing more than to yell and push two characters together because they’re perfect for one another. Thankfully, they figure it out!

The Princess Bride

The Princess Bride
20th Century Fox
20th Century Fox

Arguably one of the best and most swoon-worthy romance films of all time is the 1987 movie The Princess Bride. After watching the movie, people everywhere were trying to find a partner that would say those three magic words to them, “as you wish,” while fighting off ROUS’.

The love between Westley and Buttercup isn’t only strong enough to defeat death, but it is so true they conquer a deranged prince in their effort to be together. Their love is so true that the phrase “true love” is probably said more time than actual adventures had by the main characters.

Roman Holiday

roman-holiday_YDP3hu
Paramount Pictures
Paramount Pictures

Not only did he make one of the best rom-coms in cinema, but director William Wyler also made driving a Vespa throughout Rome one of the cooler things to do while in the city. Starring Audrey Hepburn and Gregory Peck, Roman Holiday is one of those films where you want to be the main character.

When Princess Ann finds herself being “rescued” by an American reporter, she had no idea that romance was going to come into the picture. The story is the textbook definition of finding love in the most unlikely of places, and it is perfect.

Vertigo

Vertigo
Paramount Pictures
Paramount Pictures

In 1958, Alfred Hitchcock released what is considered to be one of his finest films, Vertigo. While the movie isn’t technically classified as a romance, it is very much ground in an unlikely relationship between a retired police detective and a woman contemplating jumping off a bridge.

Of course, it’s a Hitchcock film, so no one is as they seem, and the “relationship” is very unconventional. Even so, it’s emotional to see what the detective goes through in order to save the woman he loves. Even Martin Scorcese has listed Vertigo as one of his all-time favorite films.

Pretty Woman

Pretty Woman
Touchstone Pictures
Touchstone Pictures

Arguably one of the best rom-coms to come out of the 90s is Pretty Woman. Nothing makes people root for a relationship more than when the two people involved couldn’t be further from the same universe. On one end, we have Vivian, an escort, and on the other, we have Edward, a businessman.

Even so, opposites attract. And by the end of the film, the two fall for one another. Of course, their romance isn’t without its hardships, such as Vivian not accepting Edward’s help. But everything works out in the end, as it should!

Dirty Dancing

Dirty Dancing
Vestron Pictures
Vestron Pictures

Is there anyone who has seen the 1987 dance movie Dirty Dancing and not tried the epic lift Jennifer Grey and Patrick Swayze do at the end? If not, let us tell you, it is harder and less romantic than it looks simply because you’ll most likely fall on your partner.

Anyhow, the epic romance between Baby and Johnny Castle is one for the storybooks, as it is a bit forbidden since Baby’s dad doesn’t necessarily care for the working-class guy. But when it comes to two teenagers in love, nothing’s going to stop them from “having the time of their lives.”

Moonstruck

Moonstruck
Metro-Goldwyn-Mayer
Metro-Goldwyn-Mayer

Nothing says swoon-worthy rom-com drama quite like Cher falling in love with Nicholas Cage in Moonstruck. In another case of “don’t say ‘yes’ unless you’re 100 percent sure,” Cher’s character Loretta accepts a proposal from Johnny, only to find herself slowly but surely falling in love with his younger brother, Ronny, played by Cage.

And while Loretta tries to deny her feelings, Ronny has no issue going after his brother’s gal because Johnny was the reason for the accident that left the younger brother one-handed. Yea, plot twist. But Cher’s performance as the love-sick Loretta did snag her an Academy Award for Best Actress.

Up

Up
Pixar Animation
Pixar Animation

Not to make anyone cry, but the first few minutes of Up is one of the greatest love stories ever. Carl and Ellie meet when they’re kids, playing together, and making plans to visit Paradise Falls. Then they grow up, become husband and wife, and build a life together.

The tears begin to fall when Ellie passes away, leaving Carl to their large and empty house. And while Ellie is gone from the story too soon, audience members feel her presence throughout the heartwarming tale because Carl’s love for her is so strong. It’s the most feeling we’ve ever felt from a romance film, and words were never spoken.

Eternal Sunshine Of The Spotless Mind

Eternal Sunshine Of The Spotless Mind
Focus Features
Focus Features

The love between Joel and Clementine in Eternal Sunshine of the Spotless Mind was so deep that they had to go get their minds scrubbed of the other person when they broke up. But when Joel starts to have weird flashes of memories, he has to decide if their love is more important than the pain of a failed relationship.

In the end, they decide it’s worth to give their love another try. The film isn’t exactly swoon-worthy, but it shows the intricacies of relationships and what two people will do when they find one another again.

Say Anything

Say Anything
20th Century Fox
20th Century Fox

Sorry, but there are few things less romantic than John Cusack’s character Lloyd standing outside of Ione Skye’s character Diane’s house with a boom box blasting 80s music. In a tale about first love, Say Anything takes the viewer on a wild ride when overly-optimistic Lloyd goes after the unobtainable straight-A beauty queen of high school, Diane.

Things get even crazier when he realizes that she’s kind of into him as well. But it’s high school, and Diane’s father isn’t about to let some boy come in and romance his daughter. The film is a good reminder that love conquers all, even crabby fathers.

The Before Trilogy

The Before Trilogy
Columbia Pictures
Columbia Pictures

Ethan Hawke and Julie Delpy take viewers on a three-movie romance ride in the Before trilogy. With Jesse and Celine, we venture from Vienna to Paris to Greece, watching as the two embark on a long-term commitment that is rooted in lust and love.

With each film dedicated to three different times in their life, viewers see the character’s romance blossom into something that can only be described as one of the best-detailed romances in cinematic history, even if each film takes place over the course of a few hours, with nine-year intervals between each film.

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