The Top Ten Movie Couples of the Last 25 Years

By Lauren DuBois,

Each year, the movie industry releases at least 100 movies with some sort of a romantic theme or element, whether it’s an outright love story, a drama, a comedy, or even an action movie. More often than not, there’s at least a small romance sub-plot buried somewhere in almost every movie. Because of the abundance of these movies, the actors portraying the couples are key—just the slightest lack of chemistry can throw off not only the whole love story, but the entire movie as well.

With that in mind, here’s a Top 10 list of the best movie couples of the last 25 years:

10. Emma (Anne Hathaway) and Dexter (Jim Sturgess), One Day; Romantic Drama, 2011

One Day, based on the David Nicholls novel of the same name, tells the story of Emma and Dexter on the same date that marks the night they first spent together after their college graduation, throughout the years, and checks in on where they are with their lives now—their love lives, their careers, and the status of their friendship with each other. What makes them a great couple if that theirs is a love that blossomed over time, and was rooted in a deep friendship, making it the kind that was also made to last a lifetime (once they realized they were perfect for each other that is).

Quote that best captured their romance: “If you muck me about, Dexter, lead me on, or let me down, or go behind my back, I will murder you,” said Emma.

9. Landon Carter (Shane West) and Jamie Sullivan (Mandy Moore), A Walk to Remember; Romantic Drama, 2002

One of the earlier Nicholas Sparks novel adaptations brought to the big screen, about the love between two North Carolina teenagers from opposite sides of the social circle, who are thrown together after Landon gets in trouble and is forced to do community service. The beauty of their relationship was that it was something so incredibly deep and meaningful and true, the kind of love one rarely expects from high-schoolers. Though they were resistant to each other at first, they began being everything for each other. He was willing to give up everything his life had been to be with her, and then devoted his life to taking care of her after he learns she is dying from leukemia. She, meanwhile, made him into a better person. There was never a selfish moment in their entire relationship—they each gave to the other, but never took for themselves.

Quote that best captured their romance: “Jamie saved my life. She taught me everything. About life, hope, and the long journey ahead. I’ll always miss her. But our love is like the wind. I can’t see it…but I can feel it,” said Landon.

8. Claire (Vanessa Redgrave) and Lorenzo Bartolini (Franco Nero), Letters to Juliet; Romantic Dramedy, 2010

The beauty of a second chance at love is explored in this movie, where a young writer named Sophie (Amanda Seyfried), tries to help an older woman (Redgrave) find the man she once loved as a girl, after she stumbles across a 50-year-old letter she wrote to Juliet Capulet. Second chances and life-time love ooze from every pore of this movie, especially in the story of Claire and Lorenzo, who met as teens, fell in love, but went their separate ways. Now, Claire’s long-forgotten letter to Juliet, and Sophie’s response, prompts her to try and find Lorenzo again, and rekindle their love. Of course the characters had both since married and raised families, but it doesn’t stop them from rekindling the love of their youth. The beauty of casting Redgrave and Nero as the long-separated lovers, is that their real-life story is nearly the same. The two met and fell in love when they were both cast in Camelot, and even had a son together, but separated for 44 years before rekindling their romance, and marrying in 2006.

Quote that best captures their romance: “Dear Claire, ‘What’ and ‘if’ are two words as non-threatening as words can be. But put them together side-by-side and they have the power to haunt you for the rest of your life: What if? What if? What if? I don’t know how your story ended but if what you felt then was true love, then it’s never too late…” said Claire, reading from the letter Sophie wrote her in response.

7. Patrick Verona (Heath Ledger) and Kat Strafford (Julia Stiles), 10 Things I Hate About You; Romantic Comedy, 1999

Inspired by the classic Shakespeare play “The Taming of the Shrew,” set in a modern-day high school, Kat is the undateable girl at school, whose refusal to date prevents her younger sister, the more popular and pretty Bianca, from doing so as well. Bianca schemes to get her way with the help of good guy Cameron and bad guy Joey, both of whom are courting her, in an effort to find Kat a suitable boyfriend. Enter Patrick Verona, the resident bad boy that everyone is convinced has done things as crazy as go to prison and sell his kidneys on the black market, but who really has a heart of gold underneath his gruff exterior. He and Kat initially do not get along at all, but in his efforts to court her, they manage to take their two very untrusting and screwed-up personalities and mesh them together to create an actually adorable relationship that is just a perfect match.

Quotes that best capture their romance: “It’s not every day you find a girl who’ll flash someone to get you out of detention,” said Patrick.“ I hate the way you talk to me, and the way you cut your hair. I hate the way you drive my car, I hate it when you stare. I hate your big dumb combat boots, and the way you read my mind. I hate you so much it makes me sick; it even makes me rhyme. I hate the way you’re always right, I hate it when you lie. I hate it when you make me laugh, even worse when you make me cry. I hate it when you’re not around, and the fact that you didn’t call. But mostly I hate the way I don’t hate you. Not even close, not even a little bit, not even at all,” said Kat.

6. Edward Lewis (Richard Gere) and Vivian Ward (Julia Roberts), Pretty Woman; Romantic Comedy, 1990

A 90’s Cinderella story about a nice, but ruthless, businessman who needs an escort for some social events, and hires a beautiful prostitute with whom he eventually falls in love. A true, opposite-side-of-the-tracks romance, which also features two people who manage to bring out the best in each other. She makes him see that not everything is about making money, and he in turn teaches her that she’s worth more than she’s given herself in life.

Quote that best captures their romance: “When I was a little girl, my mama used to lock me in the attic when I was bad, which was pretty often. And I would—I would pretend I was a princess…trapped in a tower by a wicked queen. And then suddenly this knight…on a white horse with these colors flying would come charging up and draw his sword. And I would wave. And he would climb up the tower and rescue me…” said Vivian.

5. Summer (Zooey Deschanel) and Tom (Joseph Gordon-Levitt), (500) Days of Summer; Romantic Dramedy, 2009
Though this story does not necessarily have the picture-perfect happy ending, Summer and Tom are still a perfect couple. Even though this is the story of unrequited love between a girl who doesn’t believe love exists at all, and the man who falls in love with her, Summer and Tom, for the brief time they have a relationship, are clearly perfect for each other in so many ways, which makes the fact that they don’t end up together more heartbreaking. They’re both incredibly quirky, and these quirks are the very thing that make them work so well together for the time they date.

Quote that best captures their romance: “I just…woke up one day and I knew…What I was never sure of with you,” said Summer.

4. Harry Burns (Billy Crystal) and Sally Wright (Meg Ryan), When Harry Met Sally; Romantic Dramedy, 1989

The iconic story of two friends who should be together because they are perfect for one another, but who take entirely too long to finally get together because of their mutual fear that sex would ruin their friendship. Ideal for its famous scene at a deli where Sally very loudly fakes an orgasm to prove to Harry that men don’t know the difference between real and fake ones, as well as just watching two best friends finally give in to the feelings they have for each other, and ultimately, falling in love.

Quote that best captures their romance: “I love that you get cold when it’s 71 degrees out. I love that it takes you an hour and a half to order a sandwich. I love that you get a little crinkle above your nose when you’re looking at me like I’m nuts. I love that after I spend the day with you, I can still smell your perfume on my clothes. And I love that you are the last person I want to talk to before I go to sleep at night. And it’s not because I’m lonely, and it’s not because it’s New Year’s Eve. I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible,” said Harry.

3. Noah Calhoun (Ryan Gosling) and Allie Hamilton (Rachel McAdams), The Notebook; Romantic Drama, 2004

One of the most popular romance movies of this generation, this Nicholas Sparks adaptation is about a poor and passionate man who falls in love with a rich young woman, and their story as they are separated by their differences, and their later rekindled romance that lasts a lifetime. This was quite possibly the best Nicholas Sparks adaptation to date, and catapulted Gosling and McAdams' careers. The movie still serves as the example for young romances to live up to, and probably will stand in such a position for a long time to come.

Quote that best captures their romance: “So it’s not gonna be easy. It’s gonna be really hard. We’re gonna have to work at this every day, but I want to do that because I want you. I want all of you, forever, you and me, every day,” said Noah.

2. Holly (Hilary Swank) and Gerry Kennedy (Gerard Butler), P.S. I Love You; Romantic Drama, 2007

Another epic love story about a widow and the letters her dead husband left her to help her move on after his death. A beautiful story about young love at first sight, a love that fate played a big role in keeping together, and a love that was so deep, that it went beyond the grave. What woman wouldn’t want to be loved so much by her husband that he set up some of the things Gerry set up for Holly, to help her carry on after she lost him? It’s one of Butler’s best roles outside of action movies as well.

Quote that best captures their romance: “P.S. I Love You,” said Gerry.

1. Westley (Cary Ewles) and Buttercup (Robin Wright), The Princess Bride; Adventure Comedy, 1987

By a technicality, this film actually is from 26 years ago (released in September of 1987), but there isn’t a single couple that can beat this one from a classic fairytale with swordplay, giants, an evil prince, a beautiful princess, kissing, and en elderly grandfather who reads the story to his sick grandson. The ultimate story of two people from different stations in life, and real love that survives pirates, kidnapping, murder plots, and even “almost death.” Buttercup, after hearing her “poor but perfect love” is suspected dead, she vows to never love again—and it’s easy to believe her. And it’s easy to believe that Westley wants nothing more from life than to serve his love and keep her satisfied.

Quotes that best capture their romance: “As you wish,” and “This is true love—you think this happens every day?” said Westley.

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