Photo: Valentine’s Day Movies
Love, like death, is one of life’s most basic and enduring constants that continues to perplex and evade definition–nobody is a master, and anybody who claims to be is either deluding themselves or selling you something. You can’t dissect and understand it with mathematical precision, yet it plays one of the most important roles in each of our lives, providing comfort, hope, and joy when times are tough.
As the pandemic has persisted to cast a pall on its first Valentine’s Day, it seems easier and more intuitive than ever to curl up with a loved one and watch a movie at home. This list isn’t simply a ranking of the 10 best romantic movies ever made, but a combination of timeless classics and more recent releases that all have a few things in common–great chemistry between leads, clever and engaging stories, and affirmations of love, all thankfully available to watch on various streaming services.
Valentine’s Day Movies
#10 ‘Palm Springs’ (2020)
The most recent film on the list and the only one to come out during quarantine, ‘Palm Springs’ takes the familiar premise of people being caught in a time loop (popularized by another film on the list) and accomplishes something that’s not only unique and heartfelt but raunchy and hilarious at the same time. Following Nyles (Samberg), a man stuck in a time loop on November 9, ‘Palm Springs’ begins with a hook-up gone wrong when Sarah (Milioti) gets caught alongside him in the very same loop. Together, they not only develop their relationship but also work to understand and break out of the cycle.
Combining whiffs of sci-fi with Samberg’s trademark comedy, ‘Palm Springs’ brings freshness and new ideas to an old concept, delivering one of the most entertaining movies of the COVID age.
Available to watch on Hulu–CLICK HERE TO WATCH
#9 ‘The Big Sick’ (2019)
One of the biggest hits of 2017 and a major turning point for lead Kumail Nanjiani, ‘The Big Sick’ tells a fictionalized account of his relationship with his wife and co-writer, Emily V. Gordon, at a time in their lives not only when Kumail’s Pakistani parents disapprove of their interethnic relationship, but also when Emily (portrayed by Zoe Kazan as Emily Gardner) falls into a medically induced coma while suffering from a mysterious and deadly illness.
It’s a bit of an unconventional love story in the sense that one of the leads is in a coma for a large part of the film, but it succeeds thanks to honest, heartfelt writing and a powerful, engaging performance by Nanjiani.
Available to watch on Amazon Prime Video–CLICK HERE TO WATCH
#8 ‘Harold and Maude’ (1971)
‘Harold and Maude’ is an incomparable dark comedy that chronicles the friendship and romance between Harold (Cort), a 20-year-old man obsessed with death, and Maude (Gordon), a 79-year-old woman who survived a Nazi concentration camp. Maude is the life-affirming counterpart to the gloomy Harold, who rebels against his detached mother’s (Pickles) attempts to steer his life-. When she arranges a date for him, he scares her off by lighting himself on fire. When she tries to enlist him in military school, he scares the recruiter by pretending to murder a pacifist protestor (who’s played by Maude).
The film’s macabre humor is all beautifully underplayed, and Maude is a subversive prototype of the Manic Pixie Dream Girl, decades before the term was coined. Driven by the soulful, naturalistic direction of the great Hal Ashby, ‘Harold and Maude’ manages to tell one of the oddest love stories ever put on cinema.
Available to watch on Pluto TV for free–CLICK HERE TO WATCH
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#7 ‘La La Land’ (2016)
Director: Damien Chazelle | Writer: Damien Chazelle
A dazzling, modern musical featuring Ryan Gosling, Emma Stone, and the auteristic style of Damien Chazelle, ‘La La Land’ is a bittersweet examination of the romance between Mia (Stone), an aspiring actress, and Seb (Gosling), a struggling jazz pianist.
‘La La Land’ is worth watching purely for its presentation of modern Los Angeles, with perfectly stylized cinematography that brings new life to the familiar SoCal hills and highways. However, the film’s through-thread is the romance between Mia and Seb, which suffers from the diverging paths of their burgeoning careers. For a distinctly innovative evocation of old Hollywood musicals, ‘La La Land’ is a unique masterpiece of our time.
Available to watch on Hulu with CINEMAX Add-on and on VOD–CLICK HERE TO WATCH
#6 ‘Queen & Slim’ (2017)
Characterized by some as a modern Bonnie and Clyde, ‘Queen & Slim’ takes the familiar premise of outlaw lovers and puts it in the context of blackness in modern America–an unimpressive Tinder date turns into a desperate flight from the law after Queen (Turner-Smith) and Slim (Kaluuya) are forced to kill a racist cop in self-defense. It’s tragically topical and the most heart-wrenching entry on the list, but it earns its place with the perfect pairing of its titular protagonists, whose romance is ultimately what carries the film.
‘Queen & Slim’ benefits from Matsoukas’ firm direction and engrossing performances by both Kaluuya and Turner-Smith, keeping you on your toes as the titular fugitives make their way across the American South–as much as it tells a beautiful love story, it’s bound to enrage you on the grounds of its poignant and relevant criticism of American racial relations.
Available to watch on HBO Max–CLICK HERE TO WATCH
#5 ‘The Princess Bride’ (1987)
Who doesn’t remember Inigo Montoya’s rehearsed self-introduction? Or how about, “Inconceivable!” ‘The Princess Bride’, chock-full of memorable scenes and characters, is one of those shared childhood memories that live in our collective subconscious. It’s easy to see how it could have such universal appeal–it’s funny, romantic, and engaging, ostensibly telling a story for kids that manages to speak to us all.
The film opens in the real world with a grandfather (Peter Falk) reading from a storybook to his sick grandson (Fred Savage), providing the narrative framework for the film. The story follows a beautiful woman named Buttercup (Wright) who falls in love with her farmboy, Westley (Elwes). After he is seemingly lost at sea, Buttercup is forced into marriage to the nefarious Prince Humperdinck (Chris Sarandon)–the remainder of the film follows Westley on his quest to rescue Buttercup, accompanied by some choice companions.
Part of the film’s broad appeal is the cheeky self-referential tone that Reiner conveys through his style and narrative framework, managing to tell what is ultimately a rather cheesy story in a way that continues to entertain decades after its release. For a safe pick that’s sure to leave you satisfied, ‘The Princess Bride’ is a great movie to watch.
Available to watch on Disney+–CLICK HERE TO WATCH
#4 ‘Eternal Sunshine of the Spotless Mind’ (2004)
Written by the inimitably postmodern Charlie Kaufman, ‘Eternal Sunshine of the Spotless Mind’ features Jim Carrey in the uncharacteristically serious role of Joel, a man who chooses to have his memories of his ex-girlfriend (Winslet) erased after discovering she has done the same.
The film unfolds in both the real world and within Joel’s memories as they gradually deteriorate. Its concept is sci-fi, at times discussing the ethical ramifications of the memory-erasing technology, but its focus is on the nature of love and memory–does erasing memories erase love?
It’s equal parts charming, cerebral, heart-wrenching, and bittersweet. Kaufman doesn’t pull punches when portraying the problems that plague relationships, and the emotional resolution is as contemplative and ambiguous as it often seems to be in life itself–in this way it may, not be as typically heartwarming as some of the other entries on the list. Nevertheless, it’s an engrossing movie that speaks to the power of love, which surpasses even the bounds of our own memories.
Available to watch on Peacock for free–CLICK HERE TO WATCH
#3 ‘Groundhog Day’ (1993)
Few films attain the same level of iconicism as ‘Groundhog Day’, the title of which has overtaken the folksy tradition after which it’s named to enter the common American lexicon as a synonym for “time loop.” The film follows Phil Connors (Murray), a contemptuous TV weatherman who travels to Punxsutawney with his producer Rita (Andie MacDowell) for their annual coverage of Groundhog Day, only to find himself waking up every morning on February 2nd.
Unlike ‘Palm Springs’, which focuses on its protagonistic couple trying to understand and break their time loop, ‘Groundhog Day’ follows Phil as he takes advantage of what is essentially a consequence-free immortality–he not only learns everything he can about every single inhabitant of the town, but also becomes a master sculptor, pianist, and learns to speak French, begging the question of just how long he actually spent reliving the same day.
However, at the film’s core lies a love story. Carried by Bill Murray’s distinctly dry wit, ‘Groundhog Day’ is a film about finding love and meaning in the most meaningless situation, which speaks to all of our greater human experiences.
Available to stream with AMC+–CLICK HERE TO WATCH
#2 ‘WALL-E’ (2019)
‘WALL-E’ is an astounding accomplishment in animation for any number of reasons, but it earns its place on this list by not only pulling off an “opposites attract” romance between two robots, but by doing so with almost no dialogue between them. In order to do so, the film’s crew watched the silent pictures of Keaton, Chaplin, and Lloyd every day for almost a year to learn how to convey any emotion needed without words. Ben Burtt, billed as the star of the film, also served as sound designer, recording 2,500 unique sounds to be used in place of dialogue, the absolute pinnacle of Foley sound effects.
Aside from the unexpected charm of its romance and Pixar’s trademark dedication to expert craftsmanship, ‘WALL-E’ is worth a watch for its increasingly relevant social criticism, which tackles consumption, pollution, the environment, technology, and corporations. It’s undeniably one of the best and most interesting films of all time, and a prime candidate for Valentine’s Day.
Available to watch on Disney+–CLICK HERE TO WATCH
#1 ‘When Harry Met Sally’ (1989)
Director: Rob Reiner | Writer: Nora Ephron
It feels obligatory to put ‘When Harry Met Sally’ at #1 in the same way that the greatest film of all time must be ‘Casablanca’, ‘Citizen Kane’, or ‘The Godfather’–nevertheless, it would be irresponsibly contrarian to do so otherwise.
Carried by Rob Reiner’s expert directing (who also directed ‘The Princess Bride’), Nora Ephron’s witty, insightful script, and powerhouse performances by Meg Ryan and Billy Crystal, ‘When Harry Met Sally’ revolves around one question–can a man and woman just be friends?
Interspersed throughout the movie are documentary-style interviews with fictitious older married couples, some of which are based on real stories that Ephron gathered. Sweet, sharp, and unceasingly entertaining, ‘When Harry Met Sally’ is the definitive prototype of the modern rom-com and deserves a watch.
Available to stream with Showtime–CLICK HERE TO WATCH
By Daniel Choi
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Daniel Choi is a writer who’s currently pursuing a BA in Film & Television from New York University. With a background in amateur film production, Daniel is fascinated by how artists’ cultural backgrounds inform their work, subconsciously or not, and how that work is then perceived by different audiences across time and space. He joined Hollywood Insider to promote its mission statement of substantive entertainment journalism, and hopes to enrich readers’ understandings of cinema through insightful analysis.