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(29) Days of Break-Up Movies

All the Real Girls
by Collin Souter

This is an updated version of an article I wrote five years ago called “Love Stinks! Yeah, Yeah! A Guide to the Best Break-Up Movies.” In the time since that article was published, there have been many wonderful and truthful films that clearly belong on that list, which at the time, consisted of 14 movies. The list has now been doubled with old and new titles. So, here you are—again, just in time for Valentine’s Day—29 films to help get you through the worst month of your life (29 in case it’s a leap year when you read this):

So, you’re at the video store, Valentine’s Day looms darkly on the horizon and you’ve just been dumped. Your world has taken a turn for the absolute worst. Going for walks doesn’t help, because eventually you have to come back home, and then what? Every single song on the radio is about you, your broken heart and every heated argument between you and your ex. You’ve lost 20 pounds because all food tastes like sandpaper. Your friends give you the same advice: “You’re not alone…It gets better…Surround yourself with friends…There’s plenty other fish in the sea…Get out, exorcise, meet new people, change your scene…Don’t call her…We’ll go out drinking, I promise.” It’s all bullshit, I know, but guess what?

You’re not alone.
It gets better.
Surround yourself with friends.
There’s plenty other fish in the sea.
Get out, exorcise, meet new people, and change your scene.
Don’t call him/her.

It’s all true. You just don’t see it yet. But like you, I look for movies, books, music or any other artform that offers comfort and truth. If you’re like me, you’re sick to death of Hollywood trivializing break-ups with their shrill Romantic Comedies starring perpetually beautiful people. Pain doesn’t solve itself with a Sheryl Crow montage, does it? Christ, if only! The following 28 films know exactly what you’re going through. They’re made by people who have been there, who have survived and who are still trying to figure it out.

(In alphabetical order, although #1 just so happens to be the best)

1. All the Real Girls… To me, the finest film ever made about falling in love and breaking up. David Gordon Green’s masterpiece about a love between a small town lothario and the 18-year-old sister of his best friend captures the boundless, poetic joy of first love as well as the tremendous ache of separation. Green caught some flack for inserting what many believed to be a mis-placed ode to Koyaanisquatsi (time-lapse photography of nature scenes and steel mills) that follows the initial break-up scene, but those critics have missed the point. Because that break-up exchange between Paul Schneider and Zooey Deschanel has so much realism that it almost hurts to watch, the montage that follows it simply conveys what the world turns into once that moment happens: A monotonous, joyless landscape where nature carries on even though you’d rather it didn’t. I have so much to say about this film, I could do my own DVD commentary track and still miss a lot. Most heartbreakingly truthful moment: The entire second half, but really, the break-up scene where suddenly Deschanel’s voice cuts out and Schneider says, “The words I hear, it’s like their not coming from you. It’s like they’re coming from the mouth of a stranger. Why don’t you put your fucking hair back on and come back?”

2. Annie Hall Somehow, Woody Allen’s 1977 romantic comedy hasn’t aged a day. In spite of the fashions, the background music and the attitudes, this movie can still hit you where it hurts and remains one of the most quotable movies of all time when it comes to relationships. “I could never belong to a club that would have someone like me for a member.” “We need the eggs.” “I think what we have on our hands is a dead shark.” Diane Keaton is still that treasure of a girlfriend we all hope to have (again) someday and the kind of girl we’d be scared shitless to lose. But of course, we do, otherwise it wouldn’t be on the list. Most heartbreakingly truthful moment: Trying your old material out on new girlfriends who just don’t get it (ie, the lobsters).

3. Blue Valentine Like (500) Days of Summer and Annie Hall, this bounces back and forth through time, though this one has more of a logic to it. For every bad time or argument this couple has in the course of 24 hours, we get a flashback that lies at the root of the matter(s). This is also not a comedy, although there are many humorous moments. Michelle Williams and Ryan Gosling play a couple who got married too young, raised a daughter and are now at the threshold of divorce. She wants one desperately (and has for some time). He is an eternal child who wants everything about his life to stay frozen in time and cannot understand how she can’t stand him anymore. Raw and honest, Blue Valentine is not exactly comfort food, but it just might put things in perspective. Most heartbreakingly truthful moment: “You said ‘for better or for worse’… well, this is me at my worst. But I’m gonna get better.”

4. Break-Up Date You are now free to shamelessly self-promote yourself and your work in any capacity you see fit. You’ve earned it.

5. Casablanca So, how tempting is it right now to pack up all your belongings and move to a distant land far from your ex to open a bar where you know no one will find you? Hey, you can do whatever you want now. No one’s stopping you. Just don’t be too surprised if your past catches up to you the way it did with Rick. No need to indicate in parentheses who plays one of the coolest, most sympathetic movie heroes of all time. No longer is this just required viewing for film fanatics (and, let’s face it, citizens of the world). Now, it’s a part of you. Rick’s pain is your pain. But guess what? Eventually, this will pass and you’ll be strong enough to put her on a plane at the end of your movie. She doesn’t have to break your heart twice. You can beat her to the punch next time. Not only that, but now you’re Bogart and the doofus she’s with now is Paul Henreid. Who’s cooler? That’s right. Most heartbreakingly truthful moment: (tie) “Of all the gin joints in all the towns in all the world…she walks into mine.” And certain songs being off limits.

6. Eternal Sunshine of the Spotless Mind I hate to tell you this, but I’m afraid you’re stuck in this situation and there’s no erasing it from your memory. There’s no erasing the fights you had, no erasing those moments when your ex made you feel three inches tall and certainly no erasing the memory of when they told you they were seeing someone else. But no one understands the desire to erase those painful moments like Charlie Kaufman, screenwriter of one of the most original films of the decade. In it, Jim Carrey and Kate Winslet play a couple who break up and decide they want to permanently erase each other from their memories. They do so at a clinic that specializes in such treatment, but Carrey realizes half-way through that some memories are worth keeping. I know how he feels. Have you tried throwing away every shred of evidence of your ex’s existence yet? Not as easy as it sounds. Most heartbreakingly truthful moment: Perhaps the very end, when they realize the pain, heartbreak and humility of the previous relationship will likely follow them into the next one. But we need the eggs, right?

7. (500) Days of Summer This is Annie Hall for a new generation. The narrator tells us from the outset that this is no love story of boy meets girl. Instead, it is a fractured dissection of a relationship that is clearly doomed from the start, but the male half (Joseph Gordon-Levitt) is too blind and lovestruck to see it. The movie plays with the events much in the same way we play them back in our head, shifting without logic from the good times to the bad and everything in between in no particular order. Yet it all tells the same story clearly and with the same inevitable conclusion: It didn’t work, because it wasn’t supposed to. That’s a maddening and unsatisfying conclusion, but get used to hearing it. Most heartbreakingly truthful moment: Why won’t she laugh along with the bad Ringo Starr album cover the way she used to?

8. Flannel Pajamas A wonderful, low-key drama about a couple who go through the usual motions of a relationships, from first blind date to inevitable heartbreak. The break-up material in this film hit pretty close to home for me in a way that made me feel rather uncomfortable. That’s what these movies do best. The dissolving of this relationship is one of the most realistic in any case. It happens over time. As writer/director Jeff Lipsky states so eloquently in the documentary Break-Up Date, “I really did pluck lines from movies and TV shows to use in my wedding vows instead of coming up with something that was more personal and from the heart… and little cruelties like that mount up, they fester.” Flannel Pajamas is all about those little cruelties that slowly pile up until it’s too late to do anything about them. After a while, it gets too exhausting to keep score. But everyone does. Most heartbreakingly truthful moment: “Now that she’s gone, I really wanna have a baby.”

9. Forgetting Sarah Marshall Chances are, you’re not in Hollywood and your ex isn’t famous. I don’t know how they get over these things out there. Remember when Katie Holmes broke up with Chris Klein? In no time flat, she was cavorting around with Tom Cruise who it seemed had her cast under his spell and still does to this day. I felt for Mr. Klein. Our break-ups happened at around the same time and I understood completely how and why he got into an accident while drunk driving. I had it bad, but he had it far, far worse. Anyway, the Judd Apatow-produced Forgetting Sarah Marshall is about a young musician (Jason Segel, who also wrote the movie) whose big-time actress girlfriend (Kristen Bell) breaks up with him and immediately ends up with a dopey, hunky, English rock star (Russell Brand). Segel takes a trip out to Hawaii to try and forget about her, but she happens to also be vacationing on the exact same island and in the same hotel. Who Segel ends up with in the movie is really irrelevant. It’s the fact that he ends up feeding his creativity until he mounts a wonderfully funny and sweet stage show that has nothing to do with his break-up, but probably would never have happened if the break-up never occurred. Remember that. Most heartbreakingly truthful moment: No matter how far you run away, your break-up will eventually come back to haunt you. Sorry.

10. High Fidelity Nobody knows us selfish, childlike, pop-culture obsessed, miserable bastards like Nick Hornby does. Unlike most Hollywood films about relationships and break-ups, John Cusack’s Rob Gordon character doesn’t have a snide, witty “best friend” character to give him all sorts of advice. Nope, record store owner Rob has to face the music alone. By backtracking and examining his past relationship failures, Rob takes his mind off his current failure, Laura (Iben Hjejle), but can’t ignore her much longer once he finds out about this new “fucking Ian guy!!!” The film does double duty by providing one of the best break-up soundtracks of all time. Most heartbreakingly truthful moment: One could easily put together a Top 5 list of truthful moments from this film, but the one that sticks out for me is not being able to sleep at night, because you’re obsessing over the idea that “Nobody is having better sex than Laura is having with Ian right now…in my mind!

11. Kramer vs. Kramer—I consider myself pretty blessed that I’ve never had to go through a divorce and that I never had to fight for custody of a child. That’s what Dustin Hoffman has to go through with his ex-wife (Meryl Streep) after she splits from the family unit. More than that, though, is that he has to confront his own selfishness and aloofness in the marriage that led to their divorce, itself a product of the changing times as feminism was now on the rise. Though slightly dated (the sequence in which Hoffman tries desperately and succeeds in landing a job in 24 hours is a bit painful to watch today), this 1979 Best Picture winner still retains the emotional power it held 27 years ago. Most heartbreakingly truthful moment: I’m guessing if you have a kid, it’s convincing them it’s not their fault the other person left the household.

12. Living Out Loud Almost an anti-break-up film, simply because we never see Holly Hunter burst out crying over the loss of her cheating husband. Yet, it almost makes the movie more genuine. Richard Lagravenese’s subtle comedy finds Hunter as a divorced nurse who tries to accept and control her newfound independence. Her nights consist of hanging out in lounges to hear Queen Latifah sing (before she became annoying), eating gourmet hamburgers alone in her apartment and going out to dinner with Danny DiVito, a divorcee whose daughter lies in a coma. The final moment in the film (to the tune of “Hot Fun in the Summertime”) is the sort of moment in a break-up that all dumpees strive for, a moment of pure contentment. Most heartbreakingly truthful moment: Hunter lies in bed and recounts the discussion with her ex-husband that led to the divorce, a discussion that keeps nagging…and nagging…and nagging…to the point where she contemplates jumping out the window.

13. Manhattan You may be alone, but you always have your city. Or at least, a place you love to live, I hope. Woody Allen’s gorgeous black-and-white relationship comedy is an artful valentine to the beloved city, of course, but everyone in it is either a mess or fast on their way to becoming one. This is more about working up the courage to break-up and be on one’s own. Is it actually easier to stay in a relationship that has either gone a bit stale or has no possibility of a future? This movie is historically interesting, of course, in the way it foreshadowed Allen’s own personal life 12 years later and even though it’s hard to shake that off when seeing him making out with a 17-year-old character (played ever so perfectly by Academy Award nominee Mariel Hemingway), their break-up is still sad to watch and the movie’s final moment couldn’t be more perfect. You’ll most likely have the Gershwin music going through your own head for a few days after watching this one. Most heartbreakingly truthful moment: The need to stay in a doomed situation, simply because it was one of your favorite things.

14. Modern Romance “One, two, three, I don’t even miss her, two, three…one, two, three, I don’t even miss her, two, three…” So chants Robert Cole (Albert Brooks) as he tries to “exorcise” his break-up away. Fat chance. After this neurotic film editor runs 1/10 of a lap, he dashes into a phone booth and calls his ex. Curse those damn telephones for making it too easy for us to obsess over calling her and calling her and calling her. Brooks’ uncomfortably hilarious comedy about a couple with an on-again-off-again relationship is also a smartly observed study of how one can lose themselves in their work one minute and lose themselves in a painful break-up the next. Oh, and pay no attention to the hideous DVD cover art from Sony. This is really a great film. Most heartbreakingly truthful moment: The unexplainable need to tell EVERYONE—from your best friend to the cashier at SportMart—that you just broke up with your girlfriend.

15. Nights and Weekends Did you try the long distance thing? Didn’t work out? This one’s for you. Joe Swanberg and Greta Gerwig collaborated on this Mumblecore project, which features them as a couple in Chicago trying to maintain their wonderful relationship whilst living far away from each other. With each visit that occurs every few months, the relationship grows seemingly more desperate and with both parties fighting to retain some kind of magic that is obviously no longer there. The final moments hurt to watch because, unlike the trappings and safety nets of Hollywood rom-com storytelling traditions, Nights and Weekends is firmly rooted in reality and, thus, their last night in a hotel room is as hard to watch as anything in Blue Valentine, though for different reasons. Most heartbreakingly truthful moment: Going through the motions of lovemaking with someone who may as well be a stranger to you.

16. Once Yes, it’s about two musicians who find each other, make incredible music and… well, maybe they fall in love, but they are both wearing fresh wounds from a previous break-up. It’s those wounds that are keeping them from taking the next step, but they still create some amazing tunes. Singers Glen Hansard and Marketa Irglova have basically preserved their then-burgeoning friendship and courtship for the screen and the result is a love story for the ages, but it lands on this list, mainly because the music provides the throughline for their aching hearts, delivered with stunning intensity in the opening scene with Hansard’s typical primal scream delivery. “Say It To Me Now” is the song and you’ll want to adopt it as your own, at least until “Falling Slowly” becomes your wedding song. Most heartbreakingly truthful moment: Declaring your cynicism for all-things-relationship.

17. One From the Heart Francis Ford Coppola’s fascinating experimental mess from 1982 is worth looking at as an interesting historical footnote to his career. This tells the story of a Las Vegas couple (Frederick Forest and Teri Garr) whose relationship crumbles on the night of their 5th anniversary. They both leave the house and try to find a lover who will meet their desires. She gets a dashing waiter (Raul Julia), he gets a hot starlet (Nastassia Kinski). So, they both win, right? Well…not exactly. This is more of a series of stage vignettes and semi-musical interludes than a straightforward narrative and it’s not hard to see why the movie bombed when it opened. It has since grown in stature with the passing of time and is widely considered Coppola’s most woefully misunderstood film. Not all of it works. The forced slapstick in the last act is painful to watch and Tom Waits’ score is slightly overbearing, but the rest is an hypnotic daydream shot entirely on the soundstages of Zoetrope Studios. Most heartbreakingly truthful moment: Forrest’s lonely “Let’s hear it for Miller Time!” followed by the hollow sound of a ticking clock.

18. Play It Again, Sam So, who’s cooler? You or Paul Henried? That’s right, you! You just don’t see it yet. In this comedy, Woody Allen plays Allan Felix, a film enthusiast who receives advice from an imaginary Humphrey Bogart. Felix has just been dumped by his girlfriend who seeks adventure and a life away from watching movies. His friends Dick and Linda (Tony Roberts and Diane Keaton) try to set him up on dates, but to no avail. Eventually, Felix falls for Linda, and why not? She’s the only woman who doesn’t make him panic. Not quite as profound or observant as Annie Hall, but still fun to watch. Its happy ending doesn’t depend on false romantic closure, but from a liberating feeling that you’re going to be just fine, with or without Bogart. Just don’t dive in too soon into that treacherous dating world. It’s truly awful out there. Most heartbreakingly truthful moment: That very first post-break-up date where you do and say everything completely wrong, while under the delusion that you’re doing everything right.

19. The Puffy Chair A realistic disintegration of two twentysomethings in a long-term relationship who need to decide whether or not they really have a future together. It starts with a roadtrip, for which Josh (co-writer/producer Mark Duplass) must drive cross country to pick up an easy chair he bought for his father on eBay. He reluctantly invites his girlfriend Emily (Kathryn Aselton), who constantly corners him into answering her questions as to where their relationship might be headed. There just might be a good reason she keeps asking (and probably more than just the fact that he keeps calling her “dude”). Writer-directors Mark and Jay Duplass' perception of how relationships function clearly comes from experience as there doesn’t seem to be a single phony moment in the film. Most heartbreakingly truthful moment: The final scene. ‘nuff said.

20. Revolutionary Road You have to wonder whatever possessed director Sam Mendes to cast his wife, Kate Winslet, as one half of a couple who are about to combust in a repressed 1950s suburban household. Leonardo DiCaprio plays the other half. He works in advertising. She stays home, but wants to be an actress. They talk of leaving the suburban landscape and jetting off to Paris where he will become a writer, just as he always dreamed. Instead, they have children, lose the dream and resent the hell out of each other until they both become completely different people. Sometimes hard to watch and unsettling, but Mendes has us on both sides of the couple’s fight. The film hard to shake off, especially with Thomas Newman’s lovely and haunting score. Most heartbreakingly truthful moment: The morning after the biggest fight of your life and things are calm. Too calm.

21. Shoot the Moon Albert Finney and Diane Keaton play a couple with four kids who decide it’s time to split up, as career interests and a mistress enter their near-perfect family unit. Jealousy and bitterness ensue as Finney is slowly but surely replaced by a new love interest. The film received some criticism for its devastating ending, in which the violent tendencies of jealousy reach their peak, but I understood completely where Finney was coming from. The lesson: Never, ever, EVER assume that your ex is completely happy with your new life. Besides, tennis is lame. Most heartbreakingly truthful moment: Separating the stuff.

22. The Social Network Whether it’s true or not (and I never did read the book The Accidental Billionaires), this movie posits that Facebook is the multi-billion dollar industry it is today because its founder, Mark Zuckerberg (Jesse Eisenberg), is a socially clueless jerk who has no idea how to maintain a real friendship. Thus, it’s no surprise that the movie opens with the one girl who was nice to him finally dumping him. Rather than feeling remorse, Zuckerberg takes his anger out on her by blogging untrue and spiteful things about her and creating a mean-spirited website. In the end, though, he is sorry. He wants to talk to her and make things right. When she refuses his attempt at starting a friendship, he figures the only way to get her attention is by creating a website that is so ubiquitous, she would have no choice by to join his social networking monster that made him the youngest billionaire in the country. So you see? Sometimes, there’s nothing wrong with losing yourself in your work. Most heartbreakingly truthful moment: To “friend” or not to “friend”…

23. Sideways In an ideal world, after a break-up you would start to re-examine your life and take stock of all your faults and do everything you can to rectify them, so as not to mess up the next prospective relationship. Miles (Paul Giamatti) does not live in that ideal world. He and his friend Jack (Thomas Hayden Church) are forever moving sideways: Not moving up in the world, not caught in a downward spiral, just stuck. Miles has been divorced for two years, but to him it feels like two weeks. Like many of us, he can’t see himself starting a new relationship with anyone, not even someone like Maya (Virginia Madsen), who shares his deep passion for fine wine. It doesn’t help matters when Jack gives unwanted updates on the whereabouts and marital status of Miles’ ex wife. I cannot reiterate this enough: The LAST thing in the world you want is an update on your ex’s love life. Most heartbreakingly truthful moment: “I’m pregnant.”

24. Splendor in the Grass Bud Stamper’s father raised him to play the field. Deanie Loomis’s mother raised her to be pure and virginal. Can Bud and Deanie’s love survive? In Elia Kazan’s 1961 melodrama starring Warren Beatty and Natalie Wood as the doomed pair, ideals concerning social status, pre-marital sex and generation gaps get woven within the fabric of a story about first love and first break-up. As Bud drifts away, Deanie retreats into an abyss of heartbreak and (literally) almost drowns. Yes, it’s dated and somewhat corny by today’s standards, but there’s no denying the ageless beauty of the two lead performances, particularly Wood. It’s a true heartbreaker, but if you’re down in the dumps while watching it, please take that Wordsworth poem to heart. If Deanie can, so can you (Granted, she had to spend two years in an institution to get to that point, but never you mind). Most heartbreakingly truthful moment: “I just wanna die.”

25. Streets of Fire Not the first thing that springs to mind when I think “break-up movie,” but I put it on here in the event that you actually decide to watch all 28 of these movies in a row one February. Eventually, amidst all this mopery, self-pity and sadness, you’re going to want something that kicks a little ass and has some grittiness to it (I hope so, anyway). Walter Hill’s 1984 “Rock and Roll Fable” takes place in “Another time, another place,,,” In it, loner vigilante Tom Cody (Michael Pere) is called back home to rescue a kidnapped singer (Diane Lane), who happens to be his ex. She lays tied in a bed by badass gang leader Raven Shaddock (Willem Dafoe). This movie is more about style, punches, a kick-ass soundtrack and a whole-lotta-attitude than about heartbreak, but there will likely be a part of you that hopes that in the future you’ll be over this person enough to be tough about it and walk off into the sunset alone with your pride intact. Also, I’m in no way advocating that it’d be cool to punch your ex in the face as a way to knock them out so they don’t follow you into gang battle. But… Most heartbreakingly truthful moment: Oh, please, it’s a Walter Hill movie.

26. Swingers If you’re lovesick and heartbroken like Mike (Jon Favreau) and you have a lovably obnoxious friend like Trent (Vince Vaughn)—who understands what you’re going through, but whose sole purpose in life is to take your mind off of it—then consider yourself a truly blessed individual. Favreau’s screenplay and performance hit all the right notes as we can plainly see Mike forever on the verge of emotional break-up relapse, even when he’s having a good time with his buddies. Sometimes, in those early months after a painful break-up, you have to force yourself to be social and smile, but when you actually do feel good, you truly do appreciate it. Like I said before, put down the orange juice, get out of the apartment and change your scene. Most heartbreakingly truthful moment: “Eventually, after you get over it, you miss the pain…because it was the one thing that kept you two together.”

27. Three Colors Trilogy: Blue, White, Red They exist as one film to me. In Blue, Juliette Binoche tries to keep a hardened façade as she deals with the death of her husband and child by trying to start a new life where nobody knows her. In Red, we witness the deterioration of two relationships, one between Irene Jacob and her distant boyfriend (whom we never see) and the other between two judges. But the key film here is White, as Karol (Zbigniew Zamachowski) must start anew after his angry and bitter ex-wife (Julie Delpy) files for divorce, mainly because of his impotence. A series of unfortunate and comic events leads Karol to a real estate scheme that could set things right as the possibility of revenge crosses his mind. Krzysztof Kieslowski’s multidimensional trilogy doesn’t address break-ups in quite the same fashion as the other films on this list, but it belongs here nonetheless. At one point in Red, Valentine (Jacob) says that she feels something important and unexplainable is happening all around her. I feel the same way when I watch these three films. Most heartbreakingly truthful moment: In White, the immediate feeling of having little to live for, so much so that you’ll gladly accept a stranger’s job offer that entails going to Poland to murder someone.

28. 2 Days in Paris There is often a sort of language barrier that exists in a relationship. You can both speak English (or whatever your native tongue may be) perfectly, but one of you may be speaking a different language entirely. That is one of the problems with the relationship between Marion (Julie Delpy) and Jack (Adam Goldberg). As they travel back to Marion’s home just outside Paris, Jack feels left out of every conversation as the language shifts to French. He asks what’s going on and she gives him an edited, watered down version of almost every conversation and confrontation. Soon, he can only rely on physical clues to help him see what is really happening between his girlfriend and all the exes they keep running into. Goldberg and Delpy (who also wrote and directed the film) have played these parts before, but their chemistry is real and their last moments together clearly come from something personal and heartfelt. Most heartbreakingly truthful moment: If we were the same people now that we were when we first got here, we could really enjoy this silly parade.

29. War of the Roses They were doomed from the start, Danny DeVito tells us. Sure, they met great, had great sex, got married and had a great life. For a little while anyway. It wasn’t long before materialism set in, ambitions changed and bedroom habits went from cute to repulsive. Oh, we can laugh at these people, but how do you know it won’t happen to you someday? We’ve all had fights and disagreement with our significant others, but have you ever just been so fed up with them that you wanted to drop a chandelier on their head? You have? Great, this flick’s for you. The Roses—Michael Douglas and Kathleen Turner—are sort of like the Middle East. Your mind does a ping-pong ball routine as you try to take sides, but eventually you just give up, sit back and helplessly watch as they destroy themselves completely. Most heartbreakingly truthful moment: “How do you hold onto someone who won’t stay? And how do you get rid of someone who won’t go?”

Five more worth mentioning…

Beautiful Girls—Not entirely about break-ups, but it has its share of insight into relationships and why they do or don’t work. Most heartbreaking moment has to be when Timothy Hutton tells Natalie Portman that she has a whole world ahead of her.

Better Off Dead—On here mainly because of its massive cult following, though it’s not as funny to me as it was 20 years ago. Still, have you noticed that every single song on every single station is now about YOU? Feel free to chuck that radio out the window at any time.

In Good Company—Again, not really a break-up movie, but the way Topher Grace’s character latches onto Dennis Quaid and his family is dead-on accurate. The last place you want to go after a break-up is to an empty house, especially when the alternative is hanging out with someone as alluring as Scarlett Johansson.

In Memory of My Father Not a break-up movie, really, but features one of the funniest battle of wills between two exes I’ve ever seen (more on that in a moment). Also worth noting is Jeremy Sisto’s paranoia about his wife crossing over to the other side.

Say Anything…--Geez, who’s been dumped more, Woody Allen or John Cusack? Again, not quite a break-up movie (its ending is way too romantic for this list), but there’s that whole middle part where he and Ione Skye have parted ways. Crowe nails that harsh reality perfectly, especially when Cusack just drives around alone, aimlessly.

Top 5 Funniest Dumpees:

1. David (Paul Rudd) in The 40 Year-Old Virgin. They were only together a few months and that was two years ago. Still, David can’t let it go. In fact, he unexpectedly confronts his ex at one of those tacky one-minute-dating services and walks out of the room with one of the funniest displays of male posturing you’ll ever see.

2. Paul Kirkwood (Michael Rapaport) in Beautiful Girls. Rather than try to win back his girlfriend (Martha Plimpton), Paul gets revenge on her by plowing all the snow in her driveway onto her garage door to keep it from opening.

3. Pat (Pat Healy) in In Memory of My Father. Pat constantly wants to start an argument with his ex at her father’s wake, but eventually he gets frustrated to the point of just wanting to start a random fist fight with anyone he can find.

4. Robbie Hart (Adam Sandler) in The Wedding Singer. Not a great movie, but what a great song!

You…don’t…know…how…much…I…need you
When…you’re…near…me…I…don’t…feel blue
When…we…kiss…I…know…you…need…me too
I can’t…believe…I found…a love…quite…so pure…and true

(Now scream)

I…hope…you’re glad…with…what…you’ve done…to me
I live…in bed…all…day long…feeling melan…choly
You’ve left…me here…all alone…tears running constantly

(Now scream)

Also noteworthy is his rendition of Love Stinks!

5. Corey Flood (Lili Taylor) in Say Anything… She has 63 songs about her ex boyfriend, Joe. One in particular, I’d like all you dumpees to take to heart. Close your eyes. Think of your ex. Think of all the things that drove you nuts about them, the really negative stuff. Now, picture your ex with the new person (the Paul Henreid to your Bogart). Now, it’s his/her turn to deal with all of that. Not you. You’re free! Now, sing to yourself, with pride…

That’ll never be me
That’ll never be me
That’ll never be, never be me, no

No, never, ever!
Don’t you even think it!

This was by no means a thoroughly researched article. Lord knows break-ups have been the inspiration for countless movies, so if I missed any, please drop me an email and I’ll continue to update the list on a yearly basis. No Dirty Love! Take care. collin@efilmcritic.com

link directly to this feature at https://www.hollywoodbitchslap.com/feature.php?feature=3151
originally posted: 01/28/11 22:29:53
last updated: 02/06/14 23:11:16
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