The Top 5 Break-Up Films of All Time

by Brett Parker

Good break-up movies are hard to find in Hollywood. If Hollywood usually favors silly and attractive romantic comedies, then break-up movies by contrast appear just as goofy and shallow. There are usually two persistent reasons for this: (1) filmmakers usually favor durable clichés and formulas over real life emotions or (2) they create situations so close to their own real life experiences that they end up lacking the outsider’s perspective the audience needs. It’s because of this that most break-up movies usually come across as too silly (The Break-Up), too sappy (For Love of the Game), or too clueless (The Hottest State).

Yet as specific films have wonderfully demonstrated, there are certainly ways to make a wonderful break-up movie. One key is to make the film’s emotions as realistic as possible. Breaking-up is a subject that has universal appeal because almost everyone from any race, color, or walk-of-life has experienced a serious heartbreak at one point in their life. It’s a part of life that everyone has dealt with and knows about. To make a break-up movie that lacks authenticity and depth would turn off way too many people and make your film more transparent then you had hoped for. Why watch a phony and clueless break-up situation when the real life version feels so much more dramatic and meaningful?

It’s also not enough to just make a realistic film, but a hopeful one as well. A good break-up movie should not only be represented with honesty, but should also offer a wise and helpful observation on the subject as well. Breaking-up may be hard, but it’s not the end of the world. Even if you have a romantic relationship that falls apart, you still have family, friends, a career, and a whole lot of living to fall back on. There’s more to life than romantic heartbreaks and the best films are the ones that understand this and try to convey it into the plot.

So since these great films are so hard to find, I’ve decided to pay tribute to the top five best films that deal with romantic break-ups. Some of these choices may seem strange, yet if you dig deep into the movie’s ideology, you will find a movie that presents heartbreak and shines light on how to deal with it:

1) Casablanca (1942)
There’s a reason why this film has held-up over the years to become one of America’s most beloved classics, one more so than the war-time drama. Casablanca finds two of classic Hollywood’s most beloved stars, Humphrey Bogart and Ingrid Bergman, dealing with the heartbreaking aftermath of a loving relationship gone terribly wrong. As war-torn lovers reuniting in Casablanca, Bogart and Bergman are sensational as heartbroken souls struggling to work out their bruised emotions. They dig so deep into their characters’ complexities that even by today’s standards their acting seems modern and authentic.

There are other films on this list that deal more directly with the subject of breaking-up, yet I place Casablanca at the top because it not only nails the roller-coaster emotions of breaking-up, but it shows our romantic hero realizing that there’s more to life than his own relationship and that things would work out better if they went their separate ways. How deep it is for Bogart to realize that his relationship “don’t amount to a hill of beans in this crazy world” and that his lover is better off with her freedom fighter husband, Victor Lazlo (Paul Henreid). Even though Casablanca owes more to classic Hollywood than modern romance, the characters have a depth and wisdom about their relationship that allows audiences of today to identify more strongly with this film than most contemporary romances.

2) High Fidelity (2000)
It’s always hard to watch a movie about a pathetic slacker who cries over losing his girlfriend. What’s great about High Fidelity, is that Rob Gordon (John Cusack) realizes he’s a pathetic slacker and wants to truly understand why his girlfriend left him and how he can improve that. As Rob embarks on a quest to examine his romantic skills by revisiting all of his former girlfriends, he begins to learn huge revelations as to why his past relationships failed and the audience begins to realize their watching one of the most insightful movies about relationships ever made. From high school hook-ups to high maintenance hotties, High Fidelity wonderfully paints a portrait of the murky romantic waters most men have to endure in this modern age.

What makes the film so refreshing is not just the insight the audience gains, but the insight Rob gains as well. By the end of the film, he has learned to grow up and be more of a man. He wins back his ex-girlfriend (Iben Hjeje) not with money or an elaborate scheme, but because he has shown maturity and tenderness. The scene in which Rob tells her why she’s the one is among the best-written scenes in modern romance (credit is also due to the wonderful British author Nick Hornby, who wrote the novel on which the film is based).

3) Swingers (1996)
Mike (Jon Favreau) left behind a loving girlfriend in New York to pursue an acting career in Los Angeles. He struggles to find work in L.A. and grows very love sick over his girl, who appears to be moving on from their relationship. What’s a guy to do? Why hang out with his buddies of course! One phone call to best pal Trent (Vince Vaughn) and Mike is out on the town hanging out at the coolest bars and meeting all sorts of new people. Who needs a girlfriend when you got great friends, swing music, and a whole ocean of attractive girls!

Swingers may be mostly about being a struggling actor in L.A. and partying on the west coast, but I call it a great break-up film because it offers wonderful alternatives from wrestling with heartbreak. As Mike has wacky social adventures with Trent and his army of swingers, we realize that spending time with friends and searching for good times just might be more fulfilling than hanging out with a girlfriend. It certainly is authentic in its convictions. Favreau also wrote the screenplay for the film and the story is largely based on his own experiences while moving out to L.A. Throw in then-indie director Doug Liman and you have an honest and hilarious look at living it up that triumphantly avoids commercial phoniness.

4) Boomerang (1992)
If most break-up movies follow pathetic whiners, then the nice thing about Boomerang is how it shows that even smooth operators get it wrong sometimes. That’s exactly what Marcus Graham (Eddie Murphy) is. He’s a cocky yet likeable advertising executive who goes through women like candy. That is until he meets Jacqueline (Robin Givens) a gorgeous business woman who has Marcus convinced that he’s found his match. Yet as Marcus tries to get serious with Jacqueline, she treats him as carelessly as he treated other women. Rejected and embarrassed, Marcus feels depressed and has no idea how to deal with heartbreak. With the help of some loyal buddies (Martin Lawrence & David Alan Grier) and a sweet new love (Halle Berry), Marcus learns some important matters of the heart and realizes what’s truly important when it comes to relationships.

Of course things are more complicated than this. Tensions flare, friendships get tested, and Marcus doesn’t have the easiest time abandoning his old ways. It is those very complications that make Boomerang so unique. On the surface, it has the appearance of your typical Eddie Murphy or office-romance comedy. While the film is very funny, it digs unexpectedly deep into the characters and we get the feeling that we’re watching real people with real life relationships. There are certain sections that seem formulaic, but there is a genuine heart beating beneath this insightful comedy.

5) Ocean’s Eleven (2001)
Not a break-up film you say? Ocean’s Eleven is nothing but a slick heist film? That may be the popular opinion, yet if you were to peel away the heist conventions, the Hollywood glamour, and the old school coolness, you would find that this movie tells the story of a heartbroken guy who plots to win back his ex-wife the best way he knows how!

As Danny Ocean (George Clooney) assembles an eleven-man crew to rob three Las Vegas casinos, he also plans to win back ex-wife Tess (Julia Roberts) who also happens to be dating the owner of those very three casinos (Andy Garcia). It proves to be a difficult task, for Tess is furious with Danny, but all goes according to plan and Tess realizes that any man who would go to such great lengths for her must be worth another try.

I realize this sounds like a bit of a stretch. But when all is said and done, you realize that the film teaches a very important lesson in breaking-up: if you truly care about someone and you sincerely put forth your all your intelligence and confidence, you just might be able to make the romantic impossible become possible! That's honestly more wisdom than can be found in a more straight-forward romantic film nowadays. If nothing else, who better to take break-up counseling from than George Clooney?