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Favorites: Five Favorite Movies To Watch During A Break-Up

Here at 25YLSite, we handle a lot of heavy lifting. Analysis, interpretation, deep discussion, introspective interviews…you name it, we’ve got it. “Favorites” takes a lighter approach to the material we normally cover. Each week, we will take you through a list of favorites—whether it’s moments, scenes, episodes, characters, lines of dialogue, whatever!—in bite-sized articles perfect for your lunch break, a dull commute, or anywhere you need to take a Moment of Zen. So, sit back and enjoy this week’s offering: Jason Sheppard picks his five favorite films to watch while going through a break-up—not that he’s currently going through a break-up, thank goodness. Trust him—those things are not fun.


Bright Lights, Big City (1988)

Michael J. Fox searches for a distraction from heartache in Bright Lights, Big City
Michael J. Fox searches for a distraction from heartache in Bright Lights, Big City

You might be the type of person who goes straight for the Nora Ephron/Nancy Shyer catalog on Netflix while going through a bad break-up. Me, personally, I like to watch movies where the main character is going through the same level of confusion, pain, uncertainty and despair as I am. The kind of pain that you feel in your bones. Yes, I know—I’m very weird that way.

In Bright Lights, Big City, we’re introduced to such a character right away. Jamie Conway (Michael J. Fox in an outstanding and far overlooked performance) is a struggling New York writer whose existence is shattered when his girlfriend, Amanda (an adorable Phoebe Cates) leaves their tiny, stuffy apartment (and lives) to pursue a life of glitz, glamour and fabulous parties among the world of high fashion modeling.

Jamie buries his grief by prowling around the New York club scene every night until 6 a.m. With the help of some sniffs of cocaine, he manages to make it into work—until he loses that as well. Grief and heartache are Jamie’s only emotions and there’s nobody around for him to pour himself out to. When his good friend (Swoozie Kurtz) offers a sympathetic shoulder, he even ruins that by trying to seduce her. Jamie attempts to win back Amanda but when she sees what a mess he’s become without her, she retreats back to her world of fashion parties while Jamie spirals farther into his own pity.

However, as the story ends, Jamie has met a bookstore clerk (Tracy Pollan) and realized the coked-up nightlife, and the vampires who inhabit it, might not be for him; there’s the glimmer of a chance that maybe, just maybe, he might wind up with a bit of happiness in his life. Lord knows, he’s earned it.

Manhattan (1979)

Woody Allen, Diane Keaton and early morning New York City in Manhattan (1978)
Woody Allen, Diane Keaton and early morning New York City

A lot of people will reach for Woody Allen’s Annie Hall while going through a break-up and quite understandably, considering that Annie Hall is a movie about a couple who breaks-up. Personally, I like to turn the lights off, lie across my couch and let Manhattan play before me. Once Gordon Willis’s amazing black and white cinematography practically paints my living room walls, surrounding me, for some reason I feel less shattered. Sure, Willis’s Godfather glow can feel like a warm candle to the viewer, but his black and white Manhattan work represents the deep uncertainty within us.

Manhattan isn’t as funny as Annie Hall. It’s a much quieter and introspective movie. There are no fantasy sequences or animation scenes. While Annie Hall (Diane Keaton) was an era-defining character, you won’t find one of those in Manhattan. Annie Hall was about a couple who drift apart when one of them decides their world is too small and wants more from life. Manhattan is about a group of aimless individuals who don’t know what they want out of life at all—or who they even want to share their life with. The characters here want to try on different people as if they’re a pair of winter gloves—curious to see what the fit might be which they may like for a while, before they realize the previous pair fit best. Unlike gloves however, people move on and they may not be there when you realize how much you need them.

Despite this, Manhattan attempts to ends on an upbeat beat note as Tracy (Mariel Hemingway, portraying the movie’s symbol of innocence and goodness) tells Isaac (Allen) that sometimes in life you have to have a “little faith” in people. Isaac doesn’t have to say anything—the look on his face which says, ‘Having faith in people will only break your heart’ is response enough. It’s also a look the viewer will not forget.

Raging Bull (1980)

Robert De Niro and Cathy Moriarty enjoy a rare moment of civility in Raging Bull
Robert De Niro and Cathy Moriarty enjoy a rare moment of civility in Raging Bull

And now you must be saying to yourself, ‘What!? The Robert De Niro boxing movie where he beats up his wife and brother? You watch that while going through a break-up?

Yes. I do.

Every time.

Raging Bull, like all if the movies on this list, is about pain, but it’s about more; rage, jealousy, self-loathing and above all else, anger. These are things I go through during a break-up (and as you can imagine, it is not fun). However, like most normal people (I hope), we find ways to get them out of our system without actually harming anyone or anything (although, I have subjected a few poor CDs to sever scratches by my hand in the past. My apologies to Sarah McLachlan and Trisha Yearwood for ruining several compact discs of your songs. It wasn’t anything personal).

Raging Bull is about a man who is loved but doesn’t know how to properly love back. The only way he can express any emotion is through physical force. His fists say the things his heart and mind are unable to (and it’s usually to someone’s face or into walls—or that poor kitchen table).

Raging Bull’s Jake is a man who could have had it all, but still manages to chase it away by his actions. Maybe that’s why this is a movie I turn to during break-ups—that feeling of having it all and then losing it—and of course, somehow trying to make sense of it.

500 Days of Summer (2009)

Joseph Gordon-Levitt envisions winning back the affections of Zooey Deschanel in 500 Days of Summer
Joseph Gordon-Levitt envisions winning back the affections of Zooey Deschanel in 500 Days of Summer

Of the movies on this list, the characters in 500 Days of Summer are not paralyzed with grief, despair, self-loathing or crippling insecurities or uncertainty. These people are, for the most part, happy. However, that just means that when it all comes crashing down for our hero, Tom (Joseph Gordon-Levitt) after his blissful one year-long romance with doe-eyed cutie Summer (Zooey Deschanel), it is then all the more painful.

Tom then goes through his existence as if a jumbo jet has landed on him during a flight touchdown. His happiness with Summer has become a memory. The year he spent with Summer has now became a miserable winter. As one often does during a break-up with someone special, we replay the events of what pushed our light, our life, our loves away. Was it a single one thing or a number of things over time that caused the person we wanted to be with decide they would rather be by themselves than with us?

Much like how Tom tries to understand what went wrong with Summer, there is no simple answer, and when Tom meets Summer one last time, she doesn’t provide one to him. Summer just had to put Tom behind her and over time, we assume Tom understands he had to put Summer behind him as well. We see this in the movie’s final moments as Tom meets Autumn (Minka Kelly). I hope things worked out between these two because if not, I’ll assume Tom’s next two girlfriend’s were named January and April (which I know aren’t really seasons, but it’s unlikely anybody names their daughter Winter or Spring).

Like Jamie at the end of Bright Lights, Big City, Tom’s story ends on a whisper of a hopeful note – which is a whole lot more than I can say about the final movie in this list.

Closer (2004)

Natalie Portman and Clive Owen in Closer (2004)
Natalie Portman and Clive Owen get Closer

I mentioned pain before, and pain is what you’ll find no shortage of within the characters of Mike Nichols’ stinging expose of fractured relationships which redefine “toxic.”

Closer is an ironic name for this movie as each character’s true instinct is to push their partner away as far as they possibly can. Then the cruel realization sets in that being alone is actually worse than being with someone who makes you feel like crap. The problem is, the other person has already found themselves another person that they can crap over. And on it goes.

Closer is a movie about four people who crap all over each other just because they can’t help themselves. A normal person watching this movie may of course ask themselves, ‘why would anyone want anything to do with these monsters?’

It’s because nobody else would have them. And when you look like Julia Roberts, Jude Law, Natalie Portman and a never-been-better Clive Owen, finding someone to play with and hurt is not that much of a challenge. The stinger here is that when one of these individuals is hurt themselves, they realize they are the only four who understand each other in that regard. Yup. These folks are messed up.

While Raging Bull’s Jake used his anger and fists to alienate those close to him, the characters in Closer use their minds to deceive each other and their mouths to shoot words that cut deeper than any blade possibly ever could. These characters are walking wounds, ready to break down to anyone, anywhere at anytime. The scene where Owen drunkenly propositions Portman (while she’s stripping for him) is one of the cinema’s finest ever examinations of weakness and anger.

Bob Dylan once said that when people approached him to express admiration for his blistering break-up album Blood On the Tracks, he would take a step back from them because he couldn’t fathom why anyone would enjoy that level of pain.

Closer is the movie version of Dylan’s ode to raging, angry hearts and lord help me, I enjoy it each and every time I watch it. Closer will leave a mark on you—whether you’re ready for it or not.


These are my my top five movies to watch during a break-up. What are some favorite movies you turn to while trying to piece that broken heart back together?


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Written by Jason Sheppard

Entertainment reporter living at the end of very cold Canada. Proud owner of a diploma in journalism and just about every CD by John Williams ever released. Favorite directors are Spielberg, Scorsese, Kubrick, Tarantino, Fellini, Lynch and Fincher. Twin Peaks, Sopranos and Six Feet Under are the greatest TV dramas ever crafted and I love 90s sitcoms such as Spin City, Sports Night, Newsradio, Seinfeld and even that one with Deadpool working in the pizza place. Click linkies below to follow me.

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