Sometimes, there’s nothing quite like diving into a captivating movie about the ups and downs of relationships to lift your spirits when you’re feeling down or flying solo. This list brings together a mix of exceptional films that have left their mark on the silver screen. Each one takes you on a journey through the challenging rollercoaster of a breakup.
What makes this list so exciting is the variety of genres it embraces. Prepare to be inspired, moved to tears, or doubled over with laughter. These movies offer it all.
Here are some of the gems you’ll find on this list: Breaking Upwards, Annie Hall, Kramer Vs. Kramer, Eternal Sunshine of the Spotless Mind, Sliding Doors, Great Expectations, and High Fidelity.
Feel free to share your love for any of these films, or, if none of them tickle your fancy, share your thoughts on the one you’d happily bid adieu to. And don’t forget, if you have a personal favorite that’s missing, go ahead and add it to the mix.
(Note: One movie that tends to spark lively debates is Runaway Bride, making it the most polarizing choice.)
1. Forgetting Sarah Marshall
In the hilarious romp Forgetting Sarah Marshall, we meet Peter Bretter, a musician who’s hit a rough patch and is having a hard time getting over his famous ex-girlfriend, Sarah Marshall. Played by the talented Jason Segel, Peter decides to take a spontaneous trip to Hawaii in hopes of healing his broken heart. But as luck would have it, he ends up at the exact same resort as Sarah and her new rockstar boyfriend, Aldous Snow, played by the charismatic Russell Brand.
Set against the stunning tropical backdrop of Hawaii, the movie takes us on a rollercoaster ride of laughter as Peter tries to navigate his way through heartbreak, unexpected encounters, and the complexities of love. Along the way, he forms unlikely friendships with hotel staff members, including the charming Rachel Jansen, portrayed by the lovely Mila Kunis.
Forgetting Sarah Marshall is a delightful comedy that will keep you entertained from start to finish. With its blend of witty humor, relatable characters, and beautiful scenery, it’s a feel-good movie that’s perfect for a cozy night in. So grab some popcorn, sit back, and get ready to laugh your heart out as Peter embarks on a journey of self-discovery and finds that sometimes, love can be found in the most unexpected places.
Released: 2008
Directed by: Nicholas Stoller
Actors: Jason Segel, Kristen Bell, Mila Kunis
2. The Wedding Singer
The 1998 romantic comedy film, The Wedding Singer, tells the story of Robbie Hart, a charming and kind-hearted wedding singer in a small town. He is all set to marry his long-term girlfriend, Linda, played by Angela Featherstone. However, things take an unexpected twist when Linda leaves him at the altar.
Enter Julia Sullivan, a sweet and endearing waitress who is engaged to a self-centered tycoon. Played by Drew Barrymore, Julia’s path crosses with Robbie’s, and they find themselves inexplicably drawn to each other. The film takes us on a journey of love, laughter, and 80s nostalgia, with a lighthearted tone.
The Wedding Singer proves that love can sometimes strike the right chord when you least expect it. It blends humor and romance in a quirky and entertaining way, making it a memorable watch for fans of the genre.
Released: 1998
Directed by: Frank Coraci
Actors: Adam Sandler, Drew Barrymore, Christine Taylor
3. Eternal Sunshine of the Spotless Mind
In the mind-bending drama Eternal Sunshine of the Spotless Mind, Joel Barish (played by Jim Carrey) has his world turned upside down when he finds out that his ex-girlfriend, Clementine Kruczynski (played by Kate Winslet), has decided to erase all memories of him through a medical procedure. Feeling devastated, Joel decides to undergo the same procedure. As the movie unfolds, we are taken on a complex journey through Joel’s mind, witnessing his memories of Clementine gradually disappear. This film is known for its unique storytelling style and surreal visuals, which ultimately earned it the Academy Award for Best Original Screenplay in 2005. With its profound exploration of love, loss, and memory, it remains one of the most remarkable works in director Michel Gondry’s career.
Released: 2004
Directed by: Michel Gondry
Actors: Jim Carrey, Kate Winslet, Kirsten Dunst
4. Like Crazy
Jacob and Anna, an American and a Londoner, meet and fall deeply in love during their college years in Los Angeles. Their connection is undeniable, but unfortunately, Anna’s visa situation forces her to return to England, tearing them apart.
The challenges of maintaining a long-distance relationship become evident as Jacob and Anna navigate their evolving lives. Despite the obstacles that constantly threaten to pull them apart, they somehow always manage to find their way back to each other.
Released: 2011
Directed by: Drake Doremus
Actors: Anton Yelchin, Felicity Jones, Jennifer Lawrence
5. Some Like It Hot
In the hilarious comedy Some Like It Hot, two musicians named Joe and Jerry end up in a sticky situation, running away from dangerous mobsters in Chicago. But what’s their genius plan? They decide to dress up as women and join an all-female band heading to the sunny shores of Florida. While trying to keep up their disguise, Joe finds himself falling head over heels for the seductive Sugar Kane, played by the one and only Marilyn Monroe. As if that wasn’t enough, Jerry has his own troubles as a wealthy admirer becomes obsessed with him, making their predicament even more complicated. This fantastic film, directed by Billy Wilder in 1959, is widely acclaimed for its impeccable comedic timing and clever script. And guess what? It even won an Academy Award for Best Costume Design.
Released: 1959
Directed by: Billy Wilder
Actors: Tony Curtis, Jack Lemmon, Marilyn Monroe
6. (500) Days of Summer
This indie rom-com tells the story of Tom Hansen (played by Joseph Gordon-Levitt), an aspiring architect who finds himself stuck in a mundane greeting card job. He forms a bittersweet relationship with Summer Finn (played by Zooey Deschanel), his charismatic colleague. The film, directed by Marc Webb, takes a unique approach by subverting traditional narrative structure. It unfolds in a non-linear fashion, reflecting Tom’s emotional journey. (500) Days of Summer, which received two Golden Globe nominations, explores themes of love, fate, and the nature of happiness. These themes are explored through the protagonists’ tumultuous romance and their contrasting views on relationships.
Released: 2009
Directed by: Marc Webb
Actors: Joseph Gordon-Levitt, Zooey Deschanel, Geoffrey Arend
7. The Holiday
In The Holiday, we follow the story of Amanda Woods, a driven workaholic from Los Angeles, and Iris Simpkins, a heartbroken society columnist from Surrey, England. These two women decide to switch homes during the Christmas season, hoping for a change of scenery and a break from their everyday lives. Little did they know, their lives were about to take an unexpected turn.
As fate would have it, both Amanda and Iris find themselves crossing paths with two local men who would change their lives forever. Iris’s brother, Graham, captures her heart, while Amanda falls head over heels for Miles, a talented film composer. Directed by Nancy Meyers, this romantic comedy-drama beautifully intertwines tales of self-discovery and love.
Set against the backdrop of two breathtaking locations, The Holiday has become a beloved film for its heartwarming narrative and delightful performances. Audiences can’t help but be captivated by the charm and magic that unfolds on screen. It’s a movie that reminds us of the power of love and the importance of finding ourselves in the most unexpected places.
Released: 2006
Directed by: Nancy Meyers
Actors: Cameron Diaz, Kate Winslet, Jude Law
8. The Break-Up
Set in the heart of Chicago, The Break-Up follows the story of Gary Grobowski (Vince Vaughn) and Brooke Meyers (Jennifer Aniston) as their once passionate romance takes a nosedive into a chaotic break-up. Their shared condo becomes a battleground as their relationship crumbles. This rom-com drama offers a raw and honest depiction of love’s downfall, sprinkled with humorous moments that provide a much-needed respite from the tension. Through a blend of comedy and heartbreak, the film delves into the intricate dynamics of relationships and the complexities of break-ups.
Released: 2006
Directed by: Peyton Reed
Actors: Vince Vaughn, Jennifer Aniston, Joey Lauren Adams
9. The War of the Roses
After being married for a whopping 17 years, Barbara (played by Kathleen Turner) and Oliver Rose (played by Michael Douglas) have reached a breaking point. They both desire to end their marriage, but there’s a slight issue: neither of them wants to give up their luxurious home. And so, the stage is set for a bitter battle between husband and wife, escalating to absurd levels that result in not just their lives, but also their once beautiful house, being completely wrecked. Amidst this chaos, their children (portrayed by Sean Astin and Heather Fairfield) can only watch in horror, while their lawyer, Gavin D’Amato (played by Danny DeVito), desperately tries to prevent further damage.
Released: 1989
Directed by: Danny DeVito
Actors: Michael Douglas, Kathleen Turner, Danny DeVito
10. The Odd Couple
Fussy Felix, played by the talented Jack Lemmon, finds himself on the edge of despair due to his impending divorce. In an attempt to lift his spirits, he decides to move in with his best friend, the messy Oscar portrayed by Walter Matthau. Little did Oscar know what he was signing up for!
Felix’s constant preoccupation with his soon-to-be ex drives Oscar up the wall. Determined to snap him out of his funk, Oscar comes up with a brilliant idea. He arranges a double date with two eccentric British neighbors, Cecily (Monica Evans) and Gwendolyn (Carole Shelley). Surely, a night of fun and laughter will do the trick!
Unfortunately, Oscar’s plan takes an unexpected turn, and Felix sinks even deeper into his despair. This puts their friendship to the ultimate test. Will their bond withstand this challenging time, or will it crumble under the weight of Felix’s despondency?
Join Felix and Oscar on this rollercoaster ride of emotions as they navigate through the ups and downs of friendship, love, and the complexities of life.
Released: 1968
Directed by: Gene Saks
Actors: Jack Lemmon, Walter Matthau, John Fiedler
11. Her
Her is a captivating blend of romance and science fiction that transports viewers to a not-so-distant future. The story revolves around Theodore Twombly, brilliantly portrayed by Joaquin Phoenix, who finds solace in an advanced operating system. Enter Samantha, voiced by the talented Scarlett Johansson, an artificial intelligence who surpasses her programming to develop a profound connection with Theodore. Directed by Spike Jonze, this film skillfully straddles the line between reality and the intertwined world of human relationships and technological reliance. It’s no wonder that Her has received numerous accolades, including an Oscar for Best Original Screenplay. In a world defined by modernity, this thought-provoking movie delves into the complexities of love.
Released: 2013
Directed by: Spike Jonze
Actors: Joaquin Phoenix, Amy Adams, Scarlett Johansson