Throughout time, there are many reasons that romantic movies stand out to us. When we feel really touched, we may be reduced to tears due to laughter or due to tragedy. Read on to find the romantic movies that are really the funniest, leaving us with a smile at the end of a busy day, and those that are the saddest, leaving us with a good cry.
Saddest: The Last Five Years
The Last Five Years is a movie based on the popular musical of the same name. It chronicles the highs and lows of Jamie and Cathy (Jeremy Jordan and Anna Kendrick). The film juxtaposes the happy songs like Cathy’s exuberant, Goodbye Until Tomorrow, (which happened at the start of their relationship) to Jamie’s heavy, I Could Never Rescue You (when Jamie writes a good-bye note, ending the relationship).
We root for the couple all the while knowing that they won’t be together. Particularly sad and painful is Cathy’s song Still Hurting that she sings in the dark empty apartment. She sings, “Jamie is over, and Jamie is gone. Jamie’s decided it’s time to move on. Jamie has new dreams he’s building upon, and I’m still hurting.” It’s a beautiful and sad song to a beautiful and sad romantic movie, and yes, we’re still hurting.
Funniest: The Princess Bride
While this cult classic is from the 1980s, it still stands out to viewers today. We have Princess Buttercup (Robyn Wright) and her true love, Westley (Cary Elwes) at the core of the story. Their love story is sweet and funny. On top of this, we have great supporting characters like Billy Crystal’s Miracle Max.
This movie is fun and quotable. While we are caught in its adventure, we are also charmed by its humor. If that sounds inconceivable, we will only say, “You keep using that word. I do not think it means what you think it means.”
Saddest: The Fault in Our Stars
Take two terminally ill adolescents, make them fall in love with each other, and get ready to brace for the tragedy that is bound to come. In the film, our point-of-view is mainly focused on Hazel, the character who seems the most likely not to live to the end of the movie. We don’t want to spoil the movie, but expect tears and embarrassing sobs. Still, it is a lovely (but sad) romantic movie.
Funniest: Bridget Jones Diary
This modern-day adaptation of Pride and Prejudice is as funny and charming as the heroine herself. Torn between her affections for two men, the tension proves funny as well.
At one point, Mr. Darcy (Colin Firth) comes to her apartment where he finds Bridget (Renee Zellweger) in the midst of creating a fancy dinner for her friends. Bridget may be a sweet person and loyal friend, but she is a lousy cook. She makes a blue soup because she accidentally boiled blue string in with the vegetables. It’s humorous seeing her friends and romantic interest feign delight at the hideous food.
Saddest: Atonement
Atonement is a beautiful and very tragic love story. It’s so tragic, in fact, that we find it hard to watch in one sitting. The story is told from a unique perspective of a younger sister (Briony) who witnesses a romantic interaction between her older sister (Cecilia) and the housekeeper’s son (Robbie). Since she is so young, she doesn’t understand the interaction and reports him. She also misunderstands other things that happen. This causes Robbie to go to jail, and later serve in the military.
All throughout the movie, we keep hoping that Cecilia and Robbie end up together. However, knowing that the title of the movie is atonement, should have had us prepared for the ending.
Funniest: Big Sick
Inspired by comedian Kumail Nanjiani and writer Emily V. Gordon’s own romance, the movie is funny, a little sad, but ultimately, heartwarming. We see the beginning of the relationship, the cultural clash (Kumail’s family tries to arrange him a marriage to a Pakistani woman), the heartbreak, and the drama–Emily falls into a coma. A bulk of the film features Kumail at the hospital with Emily’s parents.
While the situation is hard, the comedy is great. There is a reason why this film received so much acclaim: it feels truthful, and like the best comedies–finds laughter in different circumstances, making life and love a little sweeter.
Saddest: P.S. I Love You
The premise of this film is painful: Gerry dies, and Holly (his young wife) is in intense grief. She feels broken without him, and we see memories of how much they loved each other, even when they were fighting. Since Gerry knew that he was dying, he set up a system. He wrote several letters to her that would be delivered in intervals after he died.
In some ways, this is a beautiful good-bye. In other ways, it stings. What happens when Holly gets the last letter? Will it be enough for her to move on? And how can you move on from a love so great (and so sadly interrupted)?
Funniest: Forgetting Sarah Marshall
Similar to Swingers, in Forgetting Sarah Marshall we watch our main character, Peter (Jason Segel) recover from a break-up and get his groove back. When Sarah (Kristen Bell) breaks up with him, Peter cries, bent over and nude. Truly vulnerable, this moment is played for laughs. Later, he decides to go to Hawaii to get over his ex, only to run into her and her current beau there. Hilarity ensues.
Luckily, Peter comes to his senses, and he finds a new love interest. In addition, the film boasts multiple comic talents, such as Bill Hader as his friend. This movie provides a steady course of laughter.
Saddest: Love Story
This film is one of saddest love stories. It probably informed other tragic romantic films that discuss illness/death like The Fault in Our Stars and A Walk to Remember. Even the soundtrack is iconic and sad, it stays with us long after the film is over.
Oliver and Jenny are from different backgrounds. He is from a wealthy family, and she is from a working class family. They are college students, and they marry young. His family threatened him that they would cut off his financial resources if he married Jenny. This proves problematic later on when it’s revealed that Jenny has cancer, and he needs their money to pay for her treatments. A sad tale of love, it’s hard not to shed a tear with this one. The soundtrack, alone, would do it.
Funniest: When Harry Met Sally
If Love Story is an iconic sad romantic film, then When Harry Met Sally is an iconic romantic comedy. Two people met yet initially don’t like each other, then become friends, and later fall in love. Billy Crystal as Harry and Meg Ryan as Sally have great chemistry, and they are able to play off each other well.
There are plenty of iconic funny scenes like when Sally fakes an orgasm in a crowded restaurant to prove to Harry that women fake orgasms. At the end of the scene, a woman near them tells the waitress, “I’ll have what she’s having.” This is remembered as only one of the iconic lines from this funny film.
