The anti-rom-com is a somewhat niche genre. It entices you by making you think the film is going to be one thing, but then at a certain point in the movie, it pulls a Lucy with the football and changes course completely. Every week at SiftPop.com, we challenge our writers to choose what they think is the best movie under a certain topic related to a new release. So this week, with the release of Monday, we counted down our favorite anti-rom-coms. Let us know @SiftPop what your ranking is!

Have you ever had that relationship where you and your significant other hear that song and you know it will be yours forever? Then jump forward to six weeks after the breakup, and that same song comes on, and you rage/sob/sink into depression? When that moment hits in 500 Days of Summer, I knew it was going to be an amazing film. Specifically, it would be the best anti-rom-com ever! What sets Summer apart from the other movies in this category is the earnest performances from Joseph Gordon-Levitt and Zooey Deschanel. Working from a wonderfully believable script, the film jumps about non-sequentially, letting us see various stages of the relationship between JGL and ZD at different times. It gives you a feeling of being one of their friends observing the relationship at a distance, which, of course, we are! The film is shot beautifully with a very intimate feel, which should not be a surprise coming from director Marc Webb’s successful music video background. 500 Days of Summer perfectly portrays the giddiness, infatuation, hurt, confusion, and acceptance that anyone who has been in a relationship can relate to, and manages to do it without stooping to cliches or pointing fingers at or favoring one party over the other. What more could you possibly want from an anti-rom-com? (Donald Skidmore)

I have always been a fan of teen movies, especially those directed by John Hughes. 10 Things I Hate About You captures that spirit of John Hughes Films and couples it with its rendition of William Shakespeare’s, The Taming of the Shrew. A movie such as this doesn’t work on story alone, even when backed by arguably the greatest playwright of all time — it takes two dynamic leads with synergy. Heath Ledger and Julia Stiles have this in spades for this film. Every time I view it, I love to see Patrick (Ledger) slowly fall in love with Kat (Stiles) and vice versa. You get to see them show vulnerability every once in a while, despite them both having very strong personalities. Another key component of this film’s success is the writing, especially all of the comedic elements. You would be hard-pressed to find a joke landing flat in this film — the timing and accuracy of the delivery of the given material is excellent. I still laugh out loud when watching, despite seeing this film countless times. I don’t hate this film, not even close, not even a little bit, not even at all. (Joe Vargas)

“Did you really see a future with this girl?” “Like… with jet packs?” Let’s talk for a second about Michael Cera’s best movie. If you haven’t seen it, Scott Pilgrim vs the World is about a bassist who, while dating a girl, meets the girl of his dreams. But in order to be with her, he has to defeat her seven evil exes in various battles. While this film is ultimately about two people falling in love, it’s more of an action comedy than it is anything else. Rather than spend time focusing on sappy time between the wannabe couple, we spend time with them as individuals while Scott works to defeat her exes. Sure, there’s flirting and romance as primary elements of this movie, but really it’s about the fights, the friendships, and the oh-so-many laughs. Everything about this movie works so well and if you haven’t seen it, you’re really missing out. (Aaron Schweitzer)

What types of characters does George Clooney play best? They are most likely a career-oriented man who is so dedicated to his profession that love is an afterthought. They probably have a career in a field that is not a positive one where people respect the work that they do. They are also bewitched by a woman who is their equal in every way and seems so far out of reach. We could be talking about Intolerable Cruelty or Up in the Air… but let’s focus on Up in the Air. Clooney fires people for a living, but loves every moment he influences the future of others. But then a young woman, played by Anna Kendrick, shakes up his work life which turns him towards the strong and confident Vera Farmiga, who changes everything for him. Does he change his outlook on life and get the perfect woman of his dreams? This one is a little more complicated than that. But do yourself a favor… check out Up in the Air. (Shane Conto)

How about a classic? If these past couple months have taught me nothing else, it’s how much fun it is to watch Cary Grant do his thing. Here, he’s playing a newspaper editor shocked by the return of his ace reporter — and ex-wife — Hildy (Rosalind Russell) and the news that she is engaged. He attempts to keep her at the paper and from marrying her fiancé the next day by having her write one last story — interviewing a man set to be executed. Actively working to break up a relationship for your own selfish gains isn’t exactly a hallmark of the rom-com playbook. However, you can certainly sense the chemistry between the two leads. The film is driven by its rapid-fire dialogue and never-ending barrage of sarcastic barbs. With the jokes flying a mile a minute, Grant and Russell don’t miss a beat. If you’re looking to brush up on some classics, this is an easy one to find and well worth the relatively limited time commitment. (Jake Bourgeois)

Most of the time if you’re in la la land, it usually means you’re in your own dream world, much like how it feels while watching La La Land, where I find myself this week for the BEC: set in the city of stars where a musical number can break out at a moments notice. You see Mia Dolan (Emma Stone), a barista with dreams of stardom, cross paths with Seb Wilder (Ryan Gosling), a musician aspiring to run his own club, in a tale of star-crossed lovers seeking their dreams in Los Angeles, much like how I tried to find fame with my short lived grunge-polka fusion band (we were never the same when our accordion player Al quit). However, much like a blue hypergiant star, it burns hot and bright, but not long as both of our leads soon learn that sometimes our paths and dreams in life do not allow for us to bring those we want along with us. This film of lovers realizing that their dreams cannot include each other might be the one I’m kicking myself over the most for not seeing sooner. The story is phenomenal, with the cast knocking each and every performance clean out of the park, making you want our leads to be together, even though you know it’s not meant to be. Not only that, but with musical numbers calling back to a golden age of cinema combined with stunning cinematography and camera work that feels like fine art, the film is a true masterpiece where every moment feels perfect and at times poignant. This combination blends into a perfect harmony with a sorrowful undertone of what could be that puts it above almost any film, and makes it worthy of the Best Picture nomination it earned. (Joseph Davis)

The ‘60s was a tremendous decade for cinema, and one reason why that was possible was because of director Mike Nichols’ timeless film, The Graduate. The story follows Benjamin Braddock (Dustin Hoffman), a young man who graduates from college, but feels an emptiness in his existence. When he begins a relationship with the married Mrs. Robinson (Anne Bancroft), Benjamin’s confused life will become even more when he soon begins dating her daughter, Elaine (Katherine Ross). The perfection of this casting can’t be overstated, as Hoffman, Bancroft, and Ross all turn in iconic performances that click so well together. With this being a comedy-drama, Nichols masters the transitions between laugh-out-loud moments and quiet heartbreak, taking us on a turbulent journey as the trio of main characters tries to make sense of their situation that is becoming more and more awkward. What makes this movie so relatable is how everyone has experienced a moment at some point in their lives when they weren’t sure where their life was headed, just like Benjamin. He’s a character whose universal appeal engages you in the issues that he faces, making this a movie one that has an abundance of truth in every frame. (Vincent Abbatecola)

I think romantic comedies (and romance overall) are often scoffed at or shrugged off because they can be depicted in a completely unrealistic way. It’s something that maybe only a fraction of the population could ever actually experience. Her, however, presents a very different approach. Somehow, a movie set in the not too distant future about a man who falls in love with his “female” operating system is one of the most complex and accurate portrayals of what romance actually looks like for a lot of people. Theodore, masterfully played by Joaquin Phoenix, is a completely average person who is living a somewhat mundane life and who has somewhat recently been through a hard break-up. After making a choice to purchase a new operating system, he meets Samantha (voiced by Scarlett Johansson in a career-defining role) and becomes attached to her. But it’s never really presented as weird. These are two characters who have legitimate chemistry who are working to get to know each other. It is one of the most stunningly accurate depictions of what it feels like to meet someone, fall in love, and eventually realize they may not be the one for you. It would have been easy for this movie to be melodramatic or insincere, but instead it fully leaned into its premise and it gave us one of the most complex love stories in recent cinema. (Nashua Doll)

When I think of the “anti-rom-com,” Before Sunrise is one of the first movies that comes to mind. I first watched it about a year ago with my wife — I’d heard the Before trilogy endlessly praised and we were looking for a romantic movie to watch one evening. But we were blown away by what the movie ended up being. It’s not so much a movie about two people (Ethan Hawke and Julie Delpy) meeting, falling in love, and living happily ever after as it is about how two people of different genders and from different cultures think about the world around them. Jesse and Céline spend the entire night together just walking around and talking in Vienna after they met on a train earlier that day. It’s a movie about people, time, philosophy, and definitely about being a certain age. Before Sunrise is probably quite unlike any movie you’ve seen before, but that just makes it even more worth a watch. (Robert Bouffard)

Ah yes, Eternal Sunshine, my favorite film of all time, believe it or not. What more can be said about this 17-year-old film? Its melancholic direction by Michel Gondry, the experimental and often whimsical score by Jon Brion, the genius script by Charlie Kaufman, and how about the career-defying performances by both Jim Carrey and Kate Winslet. There is so much to this film that easily stands out amongst the rest of the films in this subgenre. However, the reason why I love this film so much is its core themes and ideas. The themes of letting go of past relationships and accepting change can scary for many. It teaches the audience lessons on the importance of memory and the process of grief and loss (while also starting at a smaller level like a break up). This film strikes so many chords with me; it’s one of the most personal pieces of media that I hold so dearly because I saw myself in most of the film. The confusion of change and maturing over the course of time is very reminiscent of myself learning to accept that change is coming if I like it or not. And what makes me laugh the most is how this film was marketed! It is the perfect breakup movie, date movie, comfort movie, and really entrancing drama about how far human emotion can be taken before being destroyed. I will forever love Eternal Sunshine of the Spotless Mind. Even after seven rewatches, I still find new things that I missed on previous viewings and it still plays wonders here. (John Bizub)

Honorable Mentions

Silver Linings Playbook

This is a perfect romantic comedy — don’t @ me. It is also a classic example of what happens when a director gets widely lauded for a project they work on and then tries in vain to replicate it with their followups, while never quite hitting those same heights (I’m looking at you Joy and American Hustle). The way Silver Linings Playbook truly succeeds is in its casting. Its ability to make the audience buy into the actual craziness of these characters needed some top-tier actors that had great chemistry, and boy did they find some. J-Law and B-Coop play off each other so well that it has a magnetizing effect. You don’t want to look away and risk missing any expression or quip they might throw at each other. Add to that a supporting cast with the likes of Robert De Niro and Jackie Weaver behind them and you’ve got yourself a grade-A film. It’s silly, insane, and oh-so-much fun — be sure to check it out if you haven’t already! (Alice Micheli)

About Time

When somebody mentions a Richard Curtis movie, it’s extremely likely that they’re talking about Love Actually, one of the mainstays in the rom-com genre. His movie About Time, on the other hand, is decidedly more than that. There’s a fair amount of rom-com DNA present, but it’s mostly used as the way the movie sets up the actual point of its time travel narrative. Once Domhnall Gleeson’s Tim and Rachel McAdams’ Mary well and truly get together, it’s not the cap on the plot like you’d come to expect from a romantic comedy. Things progress into a story about the family unit as a whole, and Tim’s relationship with his father, played wonderfully by Bill Nighy, in particular. There’s some wonderful messaging about things that are meant to happen or meant not to happen, no matter how hard you try to force things one way or the other, and the eventual acceptance that time goes on even if you literally had the power to rewind it. It’s delivered in a very “show, don’t tell” type of way. Despite the things it does mean to say about life, it’s also just packed with so much heart that it feels like the movie equivalent of a very firm hug. (Chris Bakker)

Forgetting Sarah Marshall

When I think about Forgetting Sarah Marshall, I can’t help but think how easily memorable it is. Not just that it takes the general sex comedy/romantic comedy and then goes its own way, but that so many of the characters are people I would want to hang out with. Jason Segel plays Peter, a TV composer who feels unfulfilled and is then dumped by his far more successful girlfriend who stars in the show he works for. In an attempt to get away and reset, he goes off to Hawaii, where he finds himself stuck on the island with not only her but her new boyfriend and world music sensation (Russel Brand). The film plays with some obvious romantic comedy tropes, but does well at making the story more about him, and finding happiness with or without a relationship to fill the void he had. I think that this film has a lot of heart and plays in the realm of relatability while giving us a lot of laughs and amazing characters to hang out with along the way. (Evan Lucken)

True Romance

You didn’t expect a romance movie helmed by Tony Scott and penned by Quentin Tarantino to conform to genre norms, did you? Good. This whirlwind romance between a pop culture geek and a call girl being hounded by the Sicilian Mafia after eloping with a briefcase of their cocaine certainly doesn’t conform. This is the script that helped finance Reservoir Dogs and Tarantino’s fingerprints are all over the dialogue. The interrogation scene is certainly the highlight (and one of Tarantino’s all-time personal favorites). The cast is stacked with familiar faces: Christian Slater, Patricia Arquette, Dennis Hopper, Christopher Walken, James Gandolfini, Samuel L. Jackson, Tom Sizemore, Michael Rapaport, stoner Brad Pitt, imaginary Elvis Val Kilmer, and whatever Gary Oldman is doing. It’s a crazy, stylish ride and one that’s sure to leave you entertained. (Jake Bourgeois)

Chasing Amy

Frank here to give it to you straight about Chasing Amy. This film is Kevin Smith’s junior film where he returns to make a movie on a smaller budget scale and tells a tale as old as time of boy meet girl, boy finds out the girl is a lesbian, and boy thinks a “good night of lovin’” is all that is required to “turn her back” in this somewhat anti-romantic comedy. With amazing performances by Ben Affleck and the unbelievable Joey Lauren Adams, this movie needs to be seen by more people. As a writer, this movie has very much helped shape me to be the writer I am today with the kind of stories I want to tell. When Smith made this movie, I don’t know if he ever intended to instill in me some very hard and important life lessons, but he did. Then many years later, there’s a followup scene in Jay and Silent Bob Reboot that did the same to me again. If you’ve been following my writing on this site over the past couple of years, you’ll know I always find ways to sneak in jokes. But this film firmly holds a special place in my heart to where I cannot help but be a bit more serious. (Frank Kemp)