A Cinematic Celebration of Romance
and potential date night movies for Valentine's Day
“I have so much strength in me you have no idea. I have a love in my life. It makes me stronger than anything you can imagine. I would say 'that's that', Mattress Man.”
- Barry Egan, Punch-Drunk Love
Valentine’s Day. Some people love it, some hate it, many are indifferent. I don’t mind the idea of having a singular holiday where we can celebrate love and romance. Furthermore, it’s a great excuse to snuggle up to a warm body and watch (or keep on in the background) a romantic movie. Here is a list of 10 of my favorite films to watch on the day of hearts (in no particular order). And as usual, since there are too many to list, I added plenty of bonuses at the end.
1. The Before Trilogy (1995, 2004, 2013) - dir. Richard Linklater
(Widely available for rent)
These are seemingly simple little films (all averaging under 100 minutes long), consisting of Before Sunrise, Before Sunset, and Before Midnight. They don’t have any “big” action scenes, but rather rely on a great, dialogue heavy, script performed perfectly by Julie Delpy and Ethan Hawke. Taken as a whole, the trilogy is more of an epic romance than any of the films would let on individually. It’s one of the most natural and honest romance films I’ve ever seen.
Here’s a list of all the films mentioned in this post, plus some bonuses:
2. Cinema Paradiso (1988) - dir. Giuseppe Tornatore
(Streaming on Paramount+ and widely available for rent)
This one really hits home because it’s not only about the love between a boy and a girl, but also about a love affair with cinema itself. It takes place in a small Italian village, but it is epic in scope. It is wonderfully written and directed (though stick to the theatrical cut and avoid the director’s cut) and contains one of the most beautiful soundtracks ever composed—by Ennio Morricone.
3. Punch-Drunk Love (2002) - dir. Paul Thomas Anderson
(Streaming on Kanopy & Hoopla and widely available for rent)
This has been one of my favorite films ever since I saw it in theaters. It’s quirky, surreal, contains fun homages to other films, has a weirdly wonderful soundtrack, and was Adam Sandler’s breakout dramatic role. It’s not for everyone but it’s perfect from my POV.
4. Roman Holiday (1953) - dir. William Wyler
(Streaming on Kanopy for free, Tubi & PlutoTV with ads, and Paramount+ with sub)
What better way to get romantic than be transported to where romance was invented: Rome. I first watched Roman Holiday when I was a teenager and it, along with Some Like It Hot, helped me learn to appreciate older movies. It’s a terrific rom com with the added benefit of transporting you to one of the great cities of the world.
5. Once (2007) - dir. John Carney
(Widely available for rent)
This is the little Irish film that could. With a micro budget of just $150,000, this film captured hearts around the world with its strong acting and even better music, went on to make over $20 million, and won an Oscar! Beyond those facts, the love story feels truer than most and is a joy to watch much more than once. I watched it shortly after returning from Ireland and it resonated so much with me I saw them perform live a few times and met them once.
6. Sunrise: A Song of Two Humans (1927) - dir. F. W. Murnau
(Streams for free on Hoopla, with ads on Tubi & Roku, and for rent widely)
This is the only silent film in my list (though I was tempted to add Chaplin’s City Lights) and I think it will be a pleasant surprise to anyone who watches it. It won “Unique and Artistic Picture” at the 1st Academy Awards (as well as best cinematography and Janet Gaynor won best actress) and is still considered a masterpiece by many. At 95 minutes it isn’t a huge commitment and a lot is packed into that time. The film was ahead of its time both visually and auditorily and it has an engaging and complex love story.
7. Eternal Sunshine of the Spotless Mind (2004) - dir. Michel Gondry
(Streaming on Hulu and available for rent widely)
One of my favorite films of all time, Eternal Sunshine has a bit of everything—romance, dark comedy (it’s no traditional “romcom”), drama, science fiction, surrealism. Charlie Kaufman wrote the wildly creative script, which pairs perfectly with Gondry’s incredibly creative direction. This movie really expresses well the complexities of relationships and how romantic feelings develop over time.
8. The Age of Innocence (1993) - dir. Martin Scorsese
(Streaming on Netflix & Criterion Channel and with ads on Tubi & Roku)
I think it’s all too often forgotten that Scorsese directed one of the greatest classical romantic films of all time, starring Daniel Day-Lewis, no less. I only saw this for the first time a few years ago and was impressed by Scorsese’s restrained, yet beautifully cinematic approach to Edith Wharton’s novel. It would pair well with Paul Thomas Anderson’s Phantom Thread.
9. The Lady Eve (1941) - dir. Preston Sturges
(Widely available for rent)
It’s a shame this isn’t currently streaming on any subscription services, because The Lady Eve is one of the greatest rom coms of all time. It’s also one of the best, and probably my favorite, of the screwball comedies, and it’s definitely worth paying to rent. The romantic antics are so well captured by Sturges’ slick camerawork and patient editing, which allow Barbara Stanwyck and Henry Fonda to shine as they ably perform Sturge’s amazing script.
10. The Princess Bride (1987) - dir. Rob Reiner
(Streaming Disney+ and widely available for rent)
Last, but certainly not least, how can I leave out Princess Buttercup? Inconceivable! Rob Reiner’s magical masterpiece is hilarious, endlessly quotable, and can be watched dozens of times without getting old. R.I.P. Rob Reiner. You are sorely missed.
There are so many that were painful to leave out.
Here are 20 bonus romances also worth celebrating V-Day with:
City Lights (1931) - dir. Charlie Chaplin
Legends of the Fall (1994) - dir. Edward Zwick
The Notebook (2004) - dir. Nick Cassavetes
When Harry Met Sally… (1989) - dir. Rob Reiner
Say Anything… (1989) - Cameron Crowe
Jerry Maguire (1996) - dir. Cameron Crowe
Annie Hall (1977) - dir. Woody Allen
Amelie (2001) - dir. Jean-Pierre Jeunet
Modern Romance (1981) - dir. Albert Brooks
A Matter of Life and Death (1946) - dir. Powell & Pressburger
Summertime (1955) - dir. David Lean
There’s Something About Mary (1998) - dir. The Farrelly Brothers
The Umbrellas of Cherbourg (1964) - dir. Jacques Demy
The Shape of Water (2017) - dir. Guillermo del Toro
They Came Together (2014) - dir. David Wain
Overboard (1987) - dir. Garry Marshall
The Phantom of the Opera (2004) - dir. Joel Schumacher
Crazy, Stupid, Love. (2011) - dir. Glenn Ficarra & John Requa
All the Real Girls (2003) - dir. David Gordon Green
Beauty and the Beast (1946) - dir. Jean Cocteau
And for the kiddos:
Lady and the Tramp (1955)
Up (2009)
WALL·E (2008)
Thanks for reading Ryan’s Film Almanac! This post is public so feel free to share it.














So happy to see Crazy Stupid Love make the list, extremely underrated and under seen!
Moonstruck, Shakespeare in Love, Pride & Prejudice are among my top go to romance films.
And of course there’s La La Land! I am loving all your suggestions, too hard to decide the ones to watch for the big Valentine’s Day cozy!❤️❤️❤️❤️