If I’m completely honest, romantic dramas and comedies aren’t exactly my area of expertise. This is due, in part, to my opinion that the romantic comedy genre has all but disappeared, only to be replaced by lazy, underwhelming, and often insulting rom-com look alikes. My disdain for where the genre stands has had its perks; I was promptly asked to write for Audiences Everywhere after publicly proclaiming Nicholas Sparks has been shitting all over the film industry for nearly two decades. (This either makes me the best person to write this Valentine’s Day list or the worst. I’ll leave that one up to you.) But despite my being terribly underwhelmed by much of the genre, there are some pretty incredible exceptions worth top ranking in not only the romance genre but also the top of any all-time bests list. Here are my picks for the seven best movies to watch this Valentine’s Day:

 

Harold and Maude
(Paramount Pictures, 1971)
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If I were forced to pick just one all-time favorite film, Harold and Maude would be it. Unquestionably, this isn’t a film for everyone. But for lovers of witty, peculiar, sometimes outrageous dark comedies, Harold and Maude is cinematic gold. Harold (Bud Cort), young, withdrawn, depressed, and terribly obsessed with his own mortality, stages a series of mock suicides, none of which fazes his intended audience: his mother. He meets (in surely the best meet-cute of all time) 79-year-old Maude (Ruth Gordon) whose passion for life is only matched by his fixation with death. As eyebrow raising as their friendship and subsequent May-December romance may be to most, there’s a certain rare, undeniable ease to the pairing. This is one of those rare love stories which stands unrivaled. The film, punctuated by Cat Steven’s oh-so-perfect soundtrack, is a powerful, poignant classic, woven with anti-establishment sentiments and anarchic wit. And the ending has me holding my breath every single time.

Annie Hall
(United Artists, 1977)
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My first inclination in writing this list was to choose modern day romantic comedies because 1) it would be challenging and 2) it just seemed like a cool idea. But then I remembered what a mess this genre is anymore and subsequently included no film younger than a decade old. This list initially included Casablanca and Breakfast at Tiffany’s – truly great films – that were cut because—while I love the films, the characters, the iconic shots—I don’t love the love stories. Gasp. Which brings me to the surviving “classic” pick. Admittedly, I didn’t get Annie Hall when I first saw it. (My father’s a big fan of Woody Allen films and was perhaps, at the time, a bit overzealous in sharing the film with his pre-teen daughter. Don’t worry. I promptly got my shit together.)
Touted as the first romantic comedy, Allen’s landmark film tells the disintegrating love story of Alvy Singer (Allen, essentially playing himself) and Annie Hall (Diane Keaton) in a non-linear, stream of consciousness narrative, punctuated with split screens and instances of breaking the fourth wall. Cynical, neurotic, and fiercely intelligent, Alvy is drawn to the vibrant, ditsy Annie as their incompatibilities set the stage for a sharply humorous but ultimately bittersweet story. Annie Hall, quite appropriately subtitled “a nervous romance,” serves as not only a brilliantly funny examination of romantic love, but also as a wise, candid observation of the complexities of human relationships.

The Princess Bride
(20th Century Fox, 1987)
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The Princess Bride is not only one of the best films of its genre, it’s one of the best films of all time. If you haven’t seen this movie, you’ve been undoubtedly chastised for your grave misstep time and again. I’ll spare you any further shaming if you just promise to finally get your act together and find out what you’ve been missing. The Princess Bride is a story within a story (a point that’s easy to forget while watching – you become that immersed in their world) which serves as an important narrative structure to keep audiences on board for the subsequent fantasy adventure. The Wesley-Princess Buttercup love story (played by devastatingly stunning Cary Elwes and Robin Wright) is alone every bit worthy of this list, but The Princess Bride, endlessly quotable with an impeccable cast, reaches far beyond sweet, romantic fairytale, appealing to audiences of all ages. Who could ever tire of a story about princesses, pirates, giants, poison, torture, revenge, sword fights, eels, fire swamps, and R.O.U.S.? (Disclaimer: There will be kissing. But someday you might not mind it so much.)

When Harry Met Sally
(Columbia Pictures, 1989)
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It wouldn’t be a Valentine’s Day list without a Nora Ephron classic. Founded on the age old question, “Can women and men just be friends?” When Harry Met Sally is a perfect illustration of what romantic comedies should be (and ought to be again). When Harry (Billy Crystal) meets Sally (Meg Ryan), the two are embarking on a cross country trip, both relocating to New York City after graduating from college. It’s a tale of boy meets girl, boy pisses girl off, boy meets girl again…and again…until they finally master the art of timing…ten years later, of course. Nora Ephron’s quick, witty dialogue paired with director Rob Reiner’s humanity and sincerity propels When Harry Met Sally into a league of its own. Between Sally’s iconic diner orgasm scene (“I’ll have what she’s having”) and Harry’s New Year’s Eve speech, the film expertly blends humor with romance. And the true love stories (retold by actors) at the beginning of each scene serve as an added bonus to this, one of the best romantic comedies of all time.

High Fidelity
(Buena Vista Pictures, 2000)
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Okay, so I chose High Fidelity because it’s one of my favorites, and I readily agree, it’s not one of the first flicks you’d name for a Valentine’s Day must-watch list. But it certainly earns its spot. High Fidelity, based upon Nick Hornby’s novel by the same name, keeps much of what made the novel great while still departing just enough from the work to create its own distinct audience. In the throes of their split, Rob (John Cusack) tells Laura (Iben Hjejle) that she doesn’t even rank in his top five breakups. He recounts his top five loves, and shortly thereafter, in true regretful Rob fashion, he’s naming the top five reasons he misses Laura. In his ensuing existential crisis, he seeks out his top five ex-girlfriends to figure out where it all went wrong. It’s pretty clear this is a guy whose interest in his love grows greater once she’s gone. The film and its incredible supporting cast of characters (especially Rob’s record store employees) are witty, neurotic, intelligent, charming, and surprisingly relatable. Pop culture preferences serve as the ultimate ranking and anyone and everyone is reduced to their taste in records. This isn’t a story about a great love; this is a story about relationships, the fleeting, inconsequential trysts that often liter young adulthood. Cusack is perfect, as is his supporting cast, and the will he or won’t he reclaim his girl from “what-fucking-Ian-guy” is secondary to all the rest. Fair warning: it’s impossible to watch this film without reflecting upon your own top five.

Big Fish
(Columbia Pictures, 2003)
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Since I’ve never believed Valentine’s Day should be exclusively reserved for the celebration of romantic love, Big Fish makes this list. Sure, Edward and Sandra have a pretty incredible little love story (that popcorn circus scene will always be one of my absolute favorites), but Big Fish’s true reluctant love story centers around father and son. Tired of his old man’s elaborate, fact-bending tales, Edward’s son, Will (Billy Crudup) is on a desperate quest to separate fairytale from reality before his father dies. Through Edward’s (Ewan McGregor, Albert Finney) recollections, audiences are transported from the present to his version of the past and back again, existing simultaneously in the world we know to be true and the world we hope to be true. Director Tim Burton is surprisingly restrained in this exquisite film about the complexities of relationships, the story we desire versus the story we live, and the sobering journey that is accepting our parents’ mortality.

Eternal Sunshine of the Spotless Mind
(Focus Features, 2004)
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How happy is the blameless vestal’s lot!
The world forgetting, by the world forgot.
Eternal sunshine of the spotless mind!
Each pray’r accepted, and each wish resign’d.

Eternal Sunshine of the Spotless Mind has proven to be the most challenging for me to write about simply because I firmly believe the best way to view this movie is to know little to nothing about it going in. I’ll do my best to keep it to a minimum. Joel (Jim Carrey who is appropriately understated) immediately falls in love with the magnetic Clementine (Kate Winslet) after uncharacteristically and impulsively breaking his rigid morning routine to jump on a train. They fall in love and out of love, and when Joel discovers Clementine has undergone a procedure to obliterate every memory she has of him and their relationship, he seeks the same freedom from his heartbreak. Lifting from Memento, Eternal Sunshine recounts the relationship from end to beginning (among other things) as Joel is dragged back through each memory while it vanishes from his mind, forced to relive every moment he was once so certain he couldn’t stand to keep. Eternal Sunshine of the Spotless Mind is a fascinating, heartbreaking examination of memory and its hold on our very happiness.

Honorable Mention: (500) Days of Summer, Casablanca, Breakfast at Tiffany’s, Before Sunrise, Before Sunset, Before Midnight, Brokeback Mountain, 10 Things I Hate About You, Silver Lining’s Playbook, Say Anything.

What will you be watching this Valentine’s Day?