Top 5 Breakup Movies of All Time

By: Russell J. Frank, Esq.
Last Update: October 29, 2016

As New Year's quickly approaches, some may be feeling down about their loves lost over the years. It’s essential to your overall wellbeing that you continue to laugh and entertain yourself. As the great Charlie Chaplin once said, “To truly laugh, you must be able to take your pain and play with it.” And as Charlie Chaplin would know, one of the best ways to bring laughter into your life is to escape into the world of the movies. To that end, I bring you a lighthearted review of what I believe to be the best five breakup movies of all time.

1. Better Off Dead

I lead with the classic 1980s movie Better Off Dead, which is just as enjoyable now as it was when I was a kid. Better Off Dead is a story about high school senior Lane (played by John Cusack), who has been dumped by his girlfriend Beth (Amanda Weiss) just as the best year of his life should be getting started. The movie revolves around Lane becoming obsessed with trying to win Beth back by conquering the highly dangerous K-12 snow ski slope.

Better Off Dead is classic 80s Cusack, and introduces a host of memorable characters throughout, including his best friend Charles de Mar, played by Curtis Armstrong (who famously played the character “Booger” in the Revenge of the Nerds movies), two Japanese drag racers, one of whom learned to speak English only by listening to hall-of-fame sports announcer Howard Cosell, and an unrelenting paperboy demanding back his two dollars. While Lane never wins back Beth in the end, he does end up finding new love and happiness from an unexpected source.

Best Quote:

"I really think it's in my best interest if I went out with someone more popular." – Beth on breaking up with Lane.

2. The Break-Up

The Break-Up came out in 2006 and stars two of my favorite comedic actors, Vince Vaughn and Jennifer Aniston, as they navigate their way through a very messy, and often hilarious, breakup. Having wooed Aniston’s character, Brooke, away from her boyfriend at the beginning of the movie while sitting a few seats away at a Chicago Cubs baseball game, initially the movie portrays a fun-loving, caring couple. However, as Vaughn’s character, Gary, becomes more comfortable within the relationship, more of the household and relationship responsibilities fall on Brooke, which as you might imagine, leads to some fairly serious, and many times funny, conflicts. 

What I like most about The Break-Up, aside from the dry and sarcastic humor from Vaughn, is that many of the issues this couple deals with are very real. From arguing over who buys the lemons, to who does the dishes, to determining how they will divide and/or sell their downtown Chicago condo, The Break-Up, while exaggerated for comedic purposes, is one of the more realistic examples of the issues that regular couples must navigate to have a successful relationship.  While Gary and Brooke end up going their separate ways, the journey they’ve taken and the self-reflection they’ve had to endure actually leaves the viewer optimistic for each character’s future.

Best Quote:

Gary: “Fine, I’ll help you with the dishes.”
Brooke: “Oh, come on. You know what? No. See? That’s not what I want.”
Gary: “You just said that you want me to help you do the dishes.”
Brooke: “I want you to want to do the dishes.”
Gary: “Why would I want to do the dishes? Why?”


3. Forgetting Sarah Marshall

Forgetting Sarah Marshall is one of those movies that I watch and then immediately want to watch again to memorize the best quotes. The movie is armed with an amazingly talented cast, led by Jason Segel as Peter Bretter, a music composer in the television industry who creates background music for cheesy television shows. Peter ends up meeting and dating Sarah Marshall (Kristen Bell) who is the star of a CSI-type television show that Peter works on. Early on we learn that Sarah is leaving Peter for rock star Aldous Snow (brilliantly played by Russell Brand). When Peter decides to travel to Hawaii to take his mind off being dumped, things take a turn for the funny when Sarah and Aldous end up in the villa directly adjoining Peter’s.

With smaller roles filled by Johah Hill, Paul Rudd, Mila Kunis, and Bill Hader, Forgetting Sarah Marshall hits all the comedic high notes, and while the underlying pain that Peter is going through comes across as extremely real, the levity in which the movie portrays his pain creates an enjoyable movie experience.    

Best Quote:

Sarah Marshall: “Do you want to put some clothes on?”
Peter Bretter: “Oh, would you like to pick out the outfit that you break up with me in!”


4. High Fidelity

You may notice that this is the second John Cusack movie that has made my list, so I just wanted to clarify, it’s not about John Cusack per se—he’s just made some darn fine breakup movies. High Fidelity was released in 2000 and follows the life of an independent record store owner Rob Gordon (Cusack) who recounts and then tracks down the women involved in his five worst breakups in an effort to discover why he can’t remain in stable relationships. With an amazing soundtrack and a talented cast of actors, including Jack Black, Tim Robbins, Catherine Zeta-Jones, Lisa Bonet, and Joan Cusack, High Fidelity is an underrated movie that humorously tackles the ups and downs of being in relationships that end unexpectedly and without mutual agreement. 

Best Quote:

Rob: “What came first, the music or the misery? People worry about kids playing with guns, or watching violent videos, that some sort of culture of violence will take them over. Nobody worries about kids listening to thousands, literally thousands of songs about heartbreak, rejection, pain, misery and loss. Did I listen to pop music because I was miserable? Or was I miserable because I listed to pop music?”

5. Swingers

By now, it’s possible you’ve realized that I’m a big Vince Vaughn fan. From Old School to Wedding Crashers, he’s just incredibly funny with impeccable timing, but it was really the movie Swingers that propelled Vaughn to super-stardom. Released in 1996, Swingers tells the story of Mike, played by Jon Favreau, who has moved to Los Angeles in an attempt to distance himself from a breakup with his long-time girlfriend in New York. A comedian by trade, Mike tries working the L.A. social scene with his group of struggling actor friends, including Trent, played by Vaughn, who steals the movie with his smooth wit and likability, as Mike tries to rediscover love in an unloving, new city. There are many memorable scenes throughout the movie, including an iconic trip to Las Vegas where Trent famously claims, “You always double down on 11s, baby!” and a swing dancing scene towards the end of the movie where it appears Mike is winning the heart of a new love interest, played by Heather Graham. Swingers is a delightfully funny and thoughtful movie that will make you laugh while also helping you realize the best way to deal with a hard breakup is to surround yourself with good friends and get back right back out there again.

Best Quote:

Trent: “You’re so money baby and you don’t even know it!”

Attorney Russell J. Frank is a partner at CPLS. P.A., focuses his practice areas on family and marital law, and is an avid movie-goer.

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