Cinema Smack’s Top 10 Doomed Romances

It’s Valentine’s Day! Love is in the air, candy and flower shops are raking in piles of cash, and all of the single people are scoffing at the very idea of the holiday. Yes, Valentine’s Day certainly isn’t for everyone and neither is romance in cinema. Of course, cinematic relationships are unavoidable. There’s always some kind of love interest thrown into a story even if the plot doesn’t necessarily call for one. Though, for every A Walk to Remember or The Notebook, there are just as many more dark and sinister partnerships in film. Therefore, instead of celebrating the best movie pairings, we’re going to do something a little different. This is Cinema Smack’s Top 10 Doomed Romances!

*Disclaimer: Before delving into the list, some of the usual suspects, i.e. Bonnie and Clyde and Romeo and Juliet (whichever version you’d like) didn’t make the cut. Obviously, there will be some classics left off the list as it was unbelievably difficult to whittle every movie relationship down to just ten. After all, this is Cinema Smack’s Top 10 and not a Top 10 of all time. Also, there will be some minor spoilers ahead as we have to address why these couples are doomed.*


10. Sebastian and Mia in La La Land (2016)

Alright, alright. Just one more time we have to talk La La Land. There are probably a number of you tired of hearing about this movie on this site but it can’t be helped. The film stars Ryan Gosling as Sebastian, a jazz pianist, and Emma Stone as Mia, an aspiring actress. The two keep bumping into one another before finally falling in love while also following their respective dreams. Of course, this leads to some eventual turmoil for the couple.

This one lands at #10 due to it being more lighthearted than the majority of entries on our list. There’s a lot of fun to be had in La La Land but there’s one pivotal moment where the tide changes for our characters. Following a surprise dinner from Sebastian, the harsh reality sets in that their lives are currently on separate paths with Sebastian joining a touring band. At this point, they have an all too real argument that many can relate to. After some back and forth and a slight from Sebastian, Mia gives an offended chuckle which seemingly marks the beginning of the end. Both characters seem apologetic following their inevitable separation but there’s always the question of what could’ve been had they made different decisions. This is something everyone can relate to.

9. Jack and Rose in Titanic (1997)

OK. Guilty pleasure. How could this not be on the list though? This is the second highest grossing movie of all time and it cleaned up eleven Academy Awards in 1998. Titanic also jumpstarted the careers of Leonardo DiCaprio and Kate Winslet. Most of you probably know the story by now but, for those living under a rock, it goes like this. Jack Dawson (DiCaprio) wins a third class ticket aboard the RMS Titanic in a game of poker. There, he meets Rose Dewitt Bukater (Winslet), a 17 year old first class passenger, as she contemplates jumping from the stern of the ship. Despite their difference in class and Rose’s engagement to her fiance, Cal (Billy Zane), Jack and Rose become romantically involved as the ship is set on a literal collision course with an iceberg in the middle of the Atlantic Ocean.

While Titanic is now over 20 years old and has been debated, parodied, and spoofed to death, it still holds up. It’s a little cheesy at times but it’s an intriguing film overall and a lot of work went into making it happen. The romance between Jack and Rose nears Romeo and Juliet territory with the couples unable to be together. In Titanic, this is due to difference in class as opposed to a family rivalry in Romeo and Juliet. Either way, the audience wants to see Jack and Rose together but class, an angry lover, and a sinking ship never allow the characters to realize their full potential as a couple. As one could assume from the history of the Titanic alone, this is one romance that will not end well.

8. Seth and Veronica in The Fly (1986)

Now we’re getting into the good stuff. There may not be a horror film that’s more gruesome, depressing, and tragic than David Cronenberg’s The Fly. Eccentric scientist, Seth Brundle (Jeff Goldblum), meets journalist, Veronica Quaife (Geena Davis), at a press event. Seth brings Veronica back to his warehouse/laboratory/home where he shows her the teleportation device (AKA telepods) that he invented. In exchange for her silence about the telepods, Seth agrees to give her exclusive rights to his story. The two begin a relationship but it’s thrown off the tracks following Seth testing the telepods on himself with a housefly that accidentally got into the pod with him. Seth begins to change into an insect as his mind and body deteriorate with Veronica unable to help him.

The relationship between Seth and Veronica in The Fly is absolutely heartbreaking. While it starts out strong, Seth becomes obsessed with his work following his combination with the housefly. His body begins to literally fall apart as he tries to stay away from Veronica. She constantly tries to see him and, each time she does, Seth’s evolution is more and more horrific. As he becomes more insect than man, she’s in increasingly more danger. At one point, Seth says to her, “I’m an insect who dreamt he was a man and loved it. But now the dream is over and the insect is awake. I’m saying (pause) I’ll hurt you if you stay.” The film’s final act is unforgettable and one of the most poignant endings to a horror film ever. It’s certainly more than worthy of a spot on our list of doomed romances.

7. Holden and Alyssa in Chasing Amy (1997)

Kevin Smith’s film, Chasing Amy, came out the same year as Titanic but they are not even close to the same movie. Ben Affleck stars as Holden McNeil, a comic book artist, who meets Alyssa Jones (Joey Lauren Adams), a lesbian artist in the same profession. Initially, he’s unaware of Alyssa’s sexual preference until he and his best friend, Banky Edwards (Jason Lee), bear witness to her and her girlfriend at a nightclub. Regardless, Holden and Alyssa become close friends until Holden expresses his feelings to her. They begin dating which puts a strain on Holden’s friendship with Banky. Eventually, Banky explains that Alyssa’s past may be a bit more complicated than initially thought.

Chasing Amy is definitely the most risque entry on this list as it deals with numerous sexual ideals. For some who may not be familiar with writer/director Kevin Smith’s work, it’s typically vulgar and loaded with sexual references. Though, Chasing Amy may be the most mature film he has ever made. Holden and Alyssa go through so many emotional turning points throughout the film. Discovering Alyssa is a lesbian, revealing his feelings, and not letting the past be the past are all roadblocks in Holden’s courtship of Alyssa. On top of that, there’s the rocky partnership/relationship/friendship between Holden and Banky. The three are unable to coexist together and Holden is the one throwing everything into upheaval. The final confrontation between the three is emotionally draining and a truly underrated moment in cinema.

6. Bob and Charlotte in Lost in Translation (2003)

This one’s a little bit different than all of the previous entries on our Top 10 Doomed Romances. In this case, Lost in Translation is an exclusively emotional experience instead of a physical one. Aging actor Bob Harris (Bill Murray) arrives in Tokyo to shoot a commercial for Suntory whisky. Charlotte (Scarlett Johansson), a young college graduate, stays at the same hotel as Bob with her photographer husband, John (Giovanni Ribisi). Bob and Charlotte begin to cross paths at the hotel and eventually hang out with some of Charlotte’s friends one night when they both can’t sleep. Their friendship grows as they near the end of their time in Tokyo and they leave a lasting impact on one another’s lives.

Lost in Translation boasts a relationship between its characters that simply isn’t feasible on any account. Both have issues with their spouses and obviously aren’t completely happy. However, Bob is experiencing a midlife crisis while Charlotte is essentially just beginning her life. In addition, they’re in a foreign city and their time together is limited from the get-go. As you watch the film, you feel for the two of them and, even though there’s an obvious age gap, they’re compatible. Unfortunately, it just isn’t meant to be. Before the two part ways, Bob mucks up their friendship but somehow makes up for it in the tearful goodbye between the two. If you’ve seen the film, you know what we’re talking about.

5. Tommy and Izzi in The Fountain (2006)

For The Fountain, all you have to do is listen to the soundtrack to know that it requires a space when it comes to doomed romances. The film actually is set during three different timelines but we’re going to focus mainly on the modern day one. The film follows Tommy Creo (Hugh Jackman), a neurosurgeon, whose wife, Izzi’s (Rachel Weisz), health is deteriorating due to cancer. Tommy intends to find a cure to save his wife before she ultimately succumbs to the disease. In addition, conquistador Tomás Verde is tasked to find the Tree of Life by Queen Isabella of Spain in the 16th century. The third timeline sees Tom Creo as a deep space traveler in the 26th century heading towards Xibalba with a tree in a biosphere bubble space ship.

All three timelines do relate to one another and are captivating in their own right. Though, the modern day plot is able to convey much of the story itself. Izzi appears to be accepting of death as Tommy is not. Instead of spending what little time they have left together, he puts all his time and energy into finding a cure and, quite possibly, cheating death itself. The Fountain is a film about life and death, creation and destruction. There’s also a lot up to viewer interpretation. Regardless, the relationship onscreen between Tommy and Izzi is heartbreaking. Tommy’s desire to save his wife completely overshadows the fact that her time is quickly fading. For anyone who has ever lost a loved one, The Fountain will certainly hit home. Also, the aforementioned score from Clint Mansell will chill you to the bone.

4. Theodore and Samantha in Her (2013)

Like Lost in TranslationHer is a strictly emotional relationship but not for lack of trying. This time, though, it’s between a man and his computer. Joaquin Phoenix stars as Theodore Twombly, a lonely man who works for a business that drafts personal letters for people unable to write them themselves. He purchases an artificially intelligent operating system that is equipped to learn, adapt, and evolve. The operating system, voiced by Scarlett Johansson, names herself Samantha and Theodore quickly bonds with her. As Samantha learns more about human nature and, specifically, love, the two develop an intimate relationship with one another.

At some points, Her is an unbelievably tough watch. Spike Jonze did an amazing job with the screenplay which even nabbed him an Academy Award. As heartwarming as the film can be at times, Jonze also perfects the insecurities, paranoia, and the unknown when dealing with human emotion in a relationship. While Theodore falls in love with Samantha, they’re unable to fully show it. In addition, after an awkward interaction with a surrogate body for Samantha, their relationship splinters and uncertainties begin to trickle in. This is another one of those doomed romances that had no chance of working from the start just due to the circumstances. That being said, it’s still sad to see two beings grow apart even if one is an operating system on a computer.

3. Paul and Christina in 21 Grams (2003)

This list is seriously about to get very dark. Not only is 21 Grams one of the most depressing films ever made but it’s also unbelievably underrated. Its nonlinear style is, at first, disorienting but not very hard to follow as it continues. There are three main characters in the film. The first is Paul Rivers (Sean Penn), a near-death mathematician in need of a new heart. Christina Peck (Naomi Watts) is a grieving widow who turns to drugs and alcohol to cope with the death of her husband and two children. Jack Jordan (Benicio del Toro) is a born again ex-convict whose faith is tested following a tragic accident. Their three lives intersect throughout the course of the film and lead them down a dark and treacherous path.

From the opening shots of the film, you can easily tell that things will not end well for everyone involved. A nude Christina lies on a bed while Paul smokes a cigarette. Neither look the least bit happy and, soon after, the film cuts to a bloody Paul unconscious on a floor with Christina screaming to call an ambulance. Again, 21 Grams isn’t the least bit happy. Everything about it is ugly and perverse. That’s not to say that the characters are bad people because, for the most part, they aren’t. They’re just three very unfortunate people whose fates are interconnected in the worst way possible. Without dropping a major spoiler, the relationship between Paul and Christina is absolutely twisted but equally as tragic. Unlike some of the previous entries on this list, it’s unlikely you’ve ever had a relationship quite like this.

2. Dean and Cindy in Blue Valentine (2010)

Blue Valentine lands at #2 on our list of doomed romances not because of a sinking ship, a genetically altered man turning into a fly, or from any other utter tragedies. It’s here because of how real it feels. Like 21 Grams, the story is told in a nonlinear style throughout a young couple’s courtship and, later, their failing marriage. Dean (Ryan Gosling) is a high school dropout working for a moving company when he meets Cindy (Michelle Williams), a pre-med student. Cindy’s dating someone else at the time but, after they split, her and Dean bump into each other again and begin dating. Cindy discovers that she’s pregnant and it may not be Dean’s. Unconcerned, Dean volunteers to raise the child with Cindy anyway and the two marry. As the years go by, the two begin drifting apart.

What’s so painful about watching Blue Valentine is how there aren’t really any major issues that causes the dissolution of their marriage. Dean paints houses for a living and has a bit of a drinking problem but he’s not violent or anything towards his family. You can also tell that Cindy’s life hasn’t gone according to plan despite becoming a nurse. There are just little things that eke away at the two of them such as Cindy coming across her ex-boyfriend who may be their daughter’s real father. Anyone that has gone through this kind of split with a significant other can see the writing on the wall. Even with Dean’s idea for a romantic getaway, these are two characters that love each other but their indifference and resentment towards one another has grown to the point of no return. There’s not a lot of joy to be had in Blue Valentine as a realistic look at a crumbling relationship.

1. Joel and Clementine in Eternal Sunshine of the Spotless Mind (2004)

First of all, if you haven’t seen this movie, shame on you. While Eternal Sunshine of the Spotless Mind isn’t as joyless as something like 21 Grams, as quirky as Her, or as lighthearted as La La Land, it’s a perfect mix of all of those things. It also has a very strong message and puts the whole idea of a relationship into perspective. Joel Barish (Jim Carrey) discovers that his girlfriend, Clementine Kruczynski (Kate Winslet), undergoes a procedure to have all memories of Joel erased from her mind. Understandably devastated, Joel goes to Lacuna, Inc. and demands that they wipe his memory clean of her as well. The film works in reverse as it erases the most recent memories of her to the oldest.

This is another film told in a nonlinear style but here it makes sense with the story. As Lacuna technicians, Stan (Mark Ruffalo) and Patrick (Elijah Wood), begin the process, Joel relives his memories with Clementine as they’re slowly erased. Charlie Kaufman’s wonderful script handles this relationship perfectly as Joel says good riddance to all of the bad memories. As the film wears on, though, Joel desperately tries to hang onto the good times as they’re being ripped away from him.

Eternal Sunshine is a perfect film about couples as it focuses on everything good and bad. Most people tend to focus on the negative aspects of their failed relationships and forget why they were even together in the first place. There must’ve been something good about it to dedicate that time to another person. While many people probably wish they could erase someone from their mind, this film urges people to rethink their stance. If you were able to alter your memories, would you really give them all up just because of how the story of your relationship ends? In many ways, relationships craft us into the people that we are and, to give those up, would be giving up pieces of ourselves.


That’s it for Cinema Smack’s Top 10 Doomed Romances! After all that, everyone is probably feeling great about going out and spending time with their significant others. If it’s any consolation, most relationships probably can’t get much worse than some of the ones on this list.

Were there any films not included that you wanted to see? Let us know in the comment section down below and have a Happy Valentine’s Day!

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3 Thoughts to “Cinema Smack’s Top 10 Doomed Romances”

  1. Anonymous

    What about All Good Things?

    1. Jeremie Sabourin

      I actually haven’t seen it but it has been on my list for quite some time!

  2. […] to do something a little different here on Cinema Smack today. For those who have checked out our Top 10 Doomed Romances, you know that traditional romance isn’t necessarily our thing. Today, though, we’re […]

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