WARNING! Potential spoilers on this list.
We’ve all been conditioned by Hollywood to expect a certain formula in romantic movies: the guy always gets the girl in the end. They overcome their differences, face huge obstacles, and defy all odds to stay together and live happily ever after. That’s the typical ending for great romantic films, right? Well, not always.
This list is not about movies where relationships end because of a tragic death, like Love Story. Instead, it celebrates the best movies and romantic comedies that challenge Hollywood conventions and break genre codes, even if it means sacrificing audience delight. In these films, the guy doesn’t end up with the girl, there’s no happy ending, and we can’t picture a future with kids and Disney vacations.
Sometimes, romantic comedies and other relationship films reflect real life. And in real life, most relationships simply don’t work out. Not every couple is meant to overcome their differences like in The Way We Were, not every couple can defy unbeatable odds and stay together like in Casablanca, and not every couple is destined for a long-lasting relationship like in 500 Days of Summer.
Sure, we might shed a tear every time we watch Casablanca and see Bogey watch Bergman board that plane. But let’s face it, the bittersweet ending is what makes Casablanca one of the greatest films ever made. Life isn’t solely about happy endings anyway. Our entertainment should reflect some truth. So, let’s appreciate the movies where the guy doesn’t get the girl and hope that our own quest for true love is more successful.”
1. Captain America: The First Avenger
Being a superhero is no walk in the park, just ask Captain America. He knows firsthand the sacrifices heroes have to make, like giving up true love to save the day. In the midst of fighting Nazis, Captain America, played by Chris Evans, finds himself falling for Peggy, portrayed by Hayley Atwell. Their connection is undeniable, but in the end, Captain America is faced with a difficult choice: save the world from Red Skull or pursue his love with Peggy. It’s a heart-wrenching decision that highlights the loneliness that comes with being a hero.
2. Casablanca
Here’s looking at you, kid.” That’s the iconic line spoken by Rick (played by Humphrey Bogart) as he bids farewell to Ilsa (played by Ingrid Bergman), leaving audiences in tears. They might always have Paris, but why, Rick? Why did you have to send her away? The agony lingers on.
3. Cast Away
No, this isn’t about Chuck (Tom Hanks) losing dear Wilson, although that is maybe one of the saddest parts of the movie. Chuck’s girlfriend Kelly (Helen Hunt) believed he had died, and despite searching for him when he disappeared, she eventually decided to move on and marry someone else after four years.
4. Gone with the Wind
In this epic tale set during the American Civil War, we witness a captivating romance between a Southern belle and an outsider. Both characters are deeply smitten with each other, but things take a complicated turn when Scarlett, portrayed by Vivien Leigh, initially rejects Rhett, played by Clark Gable. However, as the story unfolds, she soon realizes her mistake and desperately pleads for him to return to her side.
Unfortunately, in the end, the guy doesn’t win the girl. It becomes evident that he simply doesn’t care about her tearful pleas, despite her unwavering love for him. His indifference ultimately prevents their reunion, leaving Scarlett heartbroken and longing for what could have been.
5. Big
She had the option to go with him. In the comedy classic, at the end, when Josh’s (played by Tom Hanks) wish comes true and he becomes a kid again, he asks Susan (played by Elizabeth Perkins) if she wants to join him in going back to their youth. Despite feeling tempted, the serious businesswoman decides that one childhood experience was sufficient for her.
6. Star Wars: Episode IV – A New Hope
Thankfully, in Star Wars, the guy didn’t end up with the girl. Luke and Leia had an undeniable chemistry, and they seemed like a perfect match. However, their true identities were revealed in Return of the Jedi, preventing any awkward situations from unfolding.
7. (500) Days of Summer
In Marc Webb’s postmodern, non-linear love story, “500 Days of Summer,” we’re given a clear indication right from the start that Tom and Summer won’t end up together, much like in the film “Annie Hall.” The narrator straightforwardly states, “This is not a love story. It’s a story of boy meets girl,” setting the tone for what’s to come.
Sometimes, life has a way of showing us that even the most mismatched pair, like the cynic and the dreamer, are not meant to be together. It’s truly heart-wrenching to witness Tom’s despair as he struggles to accept this reality. However, fate takes an unexpected turn when Tom crosses paths with Autumn (Minka Kelly) during a job interview. Suddenly, the tides of love appear to shift with the changing season.
8. Batman Begins
Sometimes, you know, love has to take a backseat for the greater good. Rachel, played by Katie Holmes, understands that the city of Gotham requires Batman’s presence, even if it means sacrificing their own love story. After all, what good is a superhero if he can’t win over the girl?
9. The Bodyguard
And I’ll always love you.” This heartfelt line may ring true for Rachel (Whitney Houston) and Frank (Kevin Costner), but unfortunately, the diva and the bodyguard who once saved her life weren’t exactly destined for a fairy tale ending
10. The Phantom of the Opera
The famous Andrew Lloyd Weber musical made its way to the big screen in 2004. However, even in the movies, the deformed Phantom, played by Gerard Butler, doesn’t end up with the girl of his dreams. It’s quite disheartening to see that despite all the voice lessons the Phantom gave to Christine, portrayed by Emmy Rossum, he still can’t seal the deal.
11. My Best Friend’s Wedding
Alright, let’s talk about this movie where things don’t quite go the way you expect. So, there’s this girl named Julianne, played by Julia Roberts, and she’s head over heels for her best friend Michael, who’s played by Dermot Mulroney. But here’s the catch: Michael is about to tie the knot with a gal named Kimmy, played by Cameron Diaz.
Julianne gives it a shot at wrecking their wedding plans by admitting her love for Michael. However, as the story unfolds, she comes to the realization that Michael and Kimmy are actually a match made in heaven.