The List: Best Portraits Of Romance on Film

This weekend, I will finally have the chance to see Richard Linklater’s Before Midnight, the believed-to-be final entry to what may just end up being my absolute favorite film trilogy. In 1995, Linklater brought the world Before Sunrise, a film focused on a chance meeting between Jesse (Ethan Hawke) and Celine (Julie Delpy) on a train to Europe that leads to one romantic evening spent together in Vienna. Based on a personal one-night encounter Linklater had with a woman whom he never saw again, the film was an achingly real portrait of young love between two individuals who don’t quite know what their next steps are in life. Nine years later, the sequel Before Sunset hit theaters with Jesse and Celine now older, but not quite perhaps as romantically wiser as either had expected. And now, once again nine years later, Before Midnight brings us back into their world.


Counting the Before films among the greatest on-screen portrayals of romance that I have seen, I felt it was fitting that I list some of my other favorite film romances. Now, you won’t see any typical romantic comedies on this list because for me, the more real a given relationship is the more invested I am in seeing the story of that film unfold. Unfortunately, nobody can really accuse the modern romantic comedy of capturing anything close to the realm of realism. Instead, I’ve decided to give you a list of films that range from the depressing to the absurd, but that all contain some aspect of romantic truth. Given that the film genre of depressing romantic relationship dramas is one of my absolute favorites, it should come as no shock to you that these films rank fairly high on my absolute favorite films list. And now, onto The List.

Note: Because the world has chosen to not cooperate with me anytime I attempt to watch it, Casablanca is not on here. Every time I have rented it from somewhere, I’ve gotten a copy that was either scratched or didn’t even play altogether. One of these days, hopefully I’ll get some much needed cooperation from the film gods.

Additional Note: I also decided against including films that recently made appearances on my other lists, as variety can always be refreshing. So, no The Graduate, Lolita, etc. Also, my inclusion of Before Sunset and Sunrise goes without saying, so I’m putting the focus on some of my other favs.

Honorable Mentions: City Lights (1931), Badlands (1973), Wild at Heart (1990), Paris, Texas (1984), Notorious (1946), The Apartment (1960), Breathless (1960), Blue Valentine (2010), Beginners (2010), Groundhog Day (1993), Wall-E (2008), Brokeback Mountain (2005), Lost in Translation (2003)

5. The Philadelphia Story (1940)


“You’re too good for me, George. You’re a hundred times too good. And I’d make you most unhappy, most. That is, I’d do my best to.”

We begin this list with George Cukor’s romantic comedy classic The Philadelphia Story, which you may be questioning actually fits into my reasoning for this list, but I’ll do my best to explain. The film is a ‘comedy of remarriage’, a genre of films incredibly popular at the time of the Production Code, when topics such as adultery were forbidden on-screen. The Philadelphia Story fully embraces the genre’s device of having a divorced protagonist flirt with outsiders while at the same time contemplating getting back together with their ex. In this case, protagonist Tracy Lord (Katharine Hepburn) is a divorced socialite who has plans of remarrying when her ex (Cary Grant) and a drunkard journalist (Jimmy Stewart) show up and complicate things. Now, while comedies of this era had to walk the tightrope around these extreme limitations, Cukor’s classic actually thrives in spite of said limitations. Along the way, the film comes across an incredible degree of romantic truth thanks to fantastic performances from all the principal actors. Jimmy Stewart in fact won an Oscar for his role and it remains one of my favorite screen performances to this day. And yeah, the film is breathtakingly hilarious. Now you may be asking what degree of truth this film came across. Well, it’s simply that love, in all its forms, is insane; it just so happens that this very insanity isn’t going to prevent any of us from falling in love over and over again.

4. Punch-Drunk Love (2002)


“I’m lookin’ at your face and I just wanna smash it. I just wanna fuckin’ smash it with a sledgehammer and squeeze it. You’re so pretty.”

Widely viewed as the film that proved Adam Sandler can in fact act, Paul Thomas Anderson’s fucked-up love tale took everything the masses knew about the comedian and re-purposed it to make an art-film of the highest order. Taking his penchant for angry outbursts in his mainstream comedies and turning it on its head, here Sandler’s performance as Barry Egan is the most fully realized of his career. He wears a vibrantly blue suit, he amasses a collection of pudding for frequent flyer miles, and out of pure loneliness he turns to a phone sex operator which in turn leads to an extortion attempt led by a mattress man (Philip Seymour Hoffman). It is then he falls in love with Lena Leonard (Emily Watson), a woman who is actually intrigued by the caring man underneath Barry’s awkward exterior. Barry and Lena’s romance is the center of the breathtakingly shot, incredibly strange film that seemed to polarize audiences upon release. In the years following however, it has become a classic in its own right among many film enthusiasts, mostly due to the weird romantic truths it represents. In perhaps the film’s most infamous scene, Barry and Lena are having dinner at a restaurant. Barry isn’t sure of himself and doesn’t know how to act on the date so he excuses himself and proceeds to ‘beat up the bathroom’. Sandler’s performance in PDL captures that universal feeling of romantic awkwardness, and god knows I along with many others can relate to that. Barry is only not a victim of his own self-defeatism when he allows himself to let go. Wouldn’t we all be so lucky to be able to beat up our own bathroom.

3. Eternal Sunshine of the Spotless Mind (2004)


“What a loss to spend that much time with someone, only to find out that she’s a stranger.”

Born from the mind of one of my other filmmaking idols, screenwriter Charlie Kaufman, Eternal Sunshine burst onto the film landscape in 2004 with rave reviews and a fervent following that has only seemed to grow in subsequent years. Tapping into that much dreaded time period when a romantic relationship is ending and happiness seems to be a foreign concept, the film tells the story of the attempts by Joel Barish (Jim Carrey) and Clementine Kruczynski (Kate Winslet) to erase their memories of each other through a new medical procedure. Director Michel Gondry proved to be the perfect match for Kaufman’s script, heightening the absurdity of the more sci-fi elements of the concept through visual trickery while in turn grounding the narrative with achingly real performances from his cast. Jim Carrey is the true star of the film (yet another comedian gone rouge!) as his Joel is a heartbroken man who just can’t let his love for Clementine go, even if he knows they aren’t the best match for each other. Carrey was unfortunately overlooked (yet again) by the Academy for this one and I still haven’t been able to forgive them; his performance is that good. Winslet is also brilliant and gives Clementine a manic energy that is the perfect contrast to Joel’s moptastic (I’m coining this word!) protagonist. The film ends on a moment that I haven’t been able to shake since my first viewing, as Joel and Clementine come to the realization that love is not, and never will be, perfect. Kaufman, you bastard you.

2. The Films of Woody Allen (Virtually every year since 1969)


“There must be something wrong with me, because I’ve never had a relationship with a woman that’s lasted longer than the one between Hitler and Eva Braun.”

Yes, I’m cheating, but can ya blame me? When it comes to someone with a film career so lengthy and chock full of films centered on romantic relationships of any and all variety, it’s nearly impossible to pick just one. Instead, I’m picking them all! It’s hard to believe that ever since Woody Allen burst onto the film scene in the late sixties, he’s released a film in nearly every calendar year since. But hey, that’s really just a testament to one of the greatest filmmakers to have ever lived. From Annie Hall to Manhattan to Hannah and Her Sisters to Husbands and Wives, Allen has brought the world so many cathartic stories about love lost and lost renewed, non-existent love and fantastical love, that it’s impossible to not come across at least one of his films that hits you like a ton of bricks. In nearly all of his films he is able to capture some sliver of romantic truth that you’ve either experienced yourself, or that you can relate to something a friend or family member has gone through. His films range from joyous celebrations of the romantic to heartbreaking indictments on the torturous nature of relationships. They’re often hilarious and entertaining, and can bring you to a joyous place of hope, a place of despair, or even somewhere inbetween. Later this summer, with the release of his latest Blue Jasmine, I plan to rank for you my personal favorite Woody Allen films. Until then, his entire filmography will have to do. Not all of his films are classics, but if you want to experience everything you can as a film enthusiast, the conversation truly begins and ends with this neurotic, Jewish, bespectacled genius.

1. Scenes from a Marriage (1973)


“I don’t believe people are strong all on their own. You have to have someone’s hand to hold.”

Originally conceived as a Swedish television mini-series by master filmmaker Ingmar Bergman, Scenes from a Marriage received a subsequent theatrical release here in the States the following year, and thank god for that. Scenes focuses on the relationship between college professor Johan (Erland Josephson) and divorce lawyer Marianne (Liv Ullmann), a married couple who we follow through many ups and downs over a ten year span. For me, I’ve never quite experienced anything like it and it remains one of my absolute favorite films. As a child of divorce, it was incredibly easy for me to find my entry point into the narrative and relate to the characters on a deeply personal level. It’s an ambitious and heartbreakingly real statement on the nature of marriage, relationships, and love itself. We see these characters cheat on one another, fight, love, and even hate, and it’s nearly impossible to look away. Bergman is widely viewed as one of the all-time greats and for me, his craft has never been stronger than it is here. It’s not simply a film or tv mini-series, it’s a full experience. You feel like a fly on the wall in this relationship; you’re a part of it whether you choose to be or not. Is it an incredibly happy and joyous experience to be a part of? Hell no, but boy is it real and sometimes, that’s all you can ask for. It’s a masterpiece and if you are looking for one of the best portraits of romance to ever grace a film screen, look no further.

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