The 18 Most Romantic Leading Men In Pop Culture History
Billy Dunne of Daisy Jones & The Six officially joins the club.
There’s something so hot about pathetic men. Luckily, pop culture is littered with them. They populate in books and movies and TV shows the way detritus collects on the forest floor—fresh kindling for TikTokers to transform into some heavily filtered 30-second edit set to the tune of a Hozier song.
By “pathetic,” I’m referring to that specific breed of man whose ability to contain his desire for the story’s heroine is laughably low. The tell-tale signs of a pathetic man are a passionately clenched jaw and tortured, lingering stares. This man pines helplessly, instinctively, enthusiastically, as if a mere brush with the heroine’s hand is enough sustenance to last him a lifetime. It’s not enough to merely love—he must agonise! And reciprocation of his feelings can’t come too easily, nor too swiftly.
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It’s what I like to call the art of yearning. More often than I’m willing to admit, the degree of yearning in a piece of media is directly correlated to how much I can expect to enjoy it. All this is to say: I enjoy Prime Video’s adaptation of Daisy Jones & The Six quite a lot.
This is mostly thanks to Billy Dunne (Sam Claflin), the front man of fictional ’70s band The Six who is pathetic both in the intended meaning of the word (he cheats on his saint of a wife and misses the birth of their first child) and in my definition.
After recommitting himself to a life of sobriety and fidelity, his wife, Camila (Camila Morrone), is willing to give their marriage a second shot. Unfortunately for them, their relationship gets another test with the arrival of Daisy Jones (Riley Keough), a free-spirited singer-songwriter who both aggravates and enthralls Billy on a molecular level. What results is a tale of his desperation and longing for a woman he knows he can’t be with no matter how much he may wish it so—complete with tortured stares and all.
Billy follows a long tradition of pitifully-in-love men who came before him, all of whom laid the path he so recklessly stumbles forward on now. Below, we revisit the best of yearning men in fiction, ranked according to my completely unbiased and totally nonarbitrary criteria. (Note that this ranking is less a reflection of a character’s merit than it is of the caliber of his yearning.)
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Of course, the movie with a heartbreaking song performed by Celine Dion would have a yearning man as one of its protagonists. It’s Jack’s earnestness and unabashed awe toward Kate Winslet’s Rose that probably cemented Leonardo DiCaprio’s status as Hollywood. Leading. Man. (By then, he’d also already been known for playing the stage’s original simp, Romeo Montague, in the 1996 adaptation Romeo + Juliet.)
Though a compelling performance, Jack and Rose’s love story was ultimately short-lived thanks to the iceberg in the room. We therefore didn’t get to marinate in the yearning long enough to feel the intensity of its slow burn, thus earning Jack’s place as a bookend to this list.
Y Tu Mamá También turned Gael Garcia Bernal and Diego Luna into bona fide stars and rightfully so. The cult-favorite Mexican film stars the actors as Tenoch and Julio, best friends who both fall in love with an elusive (and gorgeous) older woman, Luisa, who invites them on a sensual romp of a road trip that is teenage lust personified. Luisa, of course, isn’t a woman who can be tamed or controlled, and she eventually removes herself from the equation of their relationship. At the film’s end, however, Tenoch and Julio realize that maybe what ultimately fueled their lust for Luisa was their own burning intrigue in each other.
The 2017 adaptation reimagines the classic coming-of-age novel by Lucy Maud Montgomery, putting forth a new Anne Shirley and Gilbert Blythe for younger generations to collectively obsess over. Obsess, indeed! Gilbert (Lucas Jade Zumann) is immediately smitten with Anne (Amybeth McNulty) when he first encounters her in the woods. There are too many scenes to choose from, but a standout is in the final season, when Gilbert chances upon Anne dancing outside in front of a fire, the sparks flashing behind her as a comically strong gust of wind continuously blows through her crimson hair. Perfection.
I confess: I hated Billy in the original novel by Taylor Jenkins Reid. I found him half-baked with little redeeming qualities, and something about a man getting to feel pleasure after plunging his wife through the depths of hell doesn’t sit right with me. But Sam Claflin brings a dimension to Billy that has made me, if not a Billy apologist, then a Billy sympathiser. See: the burning in his gaze when it’s directed at Daisy, the way he closes his eyes while she’s singing as though to inhale her very presence, how he relishes in kissing her after so much pent-up rage. Help! He’s fallen in love and he can’t get up!
I debated for a long time whether or not Aragorn, son of Arathorn, deserved a spot on this list—mostly because it was difficult for me to separate my personal yearning for Aragorn from his own display of yearning (if you’ve seen this TikTok edit, then you know what I’m talking about). Ultimately, he does deserve a nod. Even battling hordes of nasty murderous orcs can’t stop him from repeatedly replaying memories of the ethereal elf, Arwen (Liv Tyler), in his mind. It’s also the thought of Arwen languishing on her deathbed that gives him the courage to summon an army of ghosts and win the battle against Sauron for Middle-earth. (Ladies! If he wanted to, he would!)
History was made in Season 4 of Insecure, in which exes Lawrence (Jay Ellis) and Issa (Issa Rae) reunite to reflect on the errors of their former relationship, looking at it through the lens of two people who have long ago grown apart just to grow back together. The episode lacks froufrou and fuss; there are no fireworks or grand gestures of love. It’s just two people, who know each other better than anyone else in the world, talking. And it's still one of the most romantic 30 minutes in television that ever exists.
Timothée Chalamet’s star-turning role in the 2017 film teems with passion. Elio is instantly enchanted by Oliver (Armie Hammer), a graduate student who comes to live with his family in Italy for a summer. As so often is the case with young love, Elio overthinks every little interaction with Oliver, his moods instantaneously leaping from pure ecstasy to misery depending on a single look or touch. It’s endearingly relatable and makes it all the more satisfying when their true feelings for each other are at last uncovered.
The yearning in this Hulu adaptation of the Sally Rooney novel elevates the Wattpad-esque miscommunication trope. Connell (Paul Mescal) is obviously in love with Marianne (Daisy Edgar-Jones), but is at times either too cowardly or too prideful to do the hard work of vulnerability that love so often requires. It makes for a deliciously winding romance that spans years, countries, and other partners. Overall, Normal People steeps itself with the simmering intensity of their mutual longing for each other.
Who yearns more than someone who made a sacred, lifelong commitment to celibacy?
The last scene in the series finale—in which Fleabag (Phoebe Waller-Bridge) explicitly confesses to the Hot Priest (Andrew Scott) that she loves him and he generously responds, “It’ll pass”—is oft interpreted as a moment of stomach-turning rejection, but we take it out of context. For most of the show, the priest is attempting (and failing) to suppress his desire for Fleabag, constantly toeing the boundaries of their relationship before completely tossing them aside altogether (reader, they have sex). By the end, he tearfully tears himself away from her! After practically begging her not to enter his church again! Lest he succumb to lust once more! The feelings are clearly reciprocated; he does yearn for Fleabag, he just yearns for Jesus Christ more.
Speaking of celibates, Grey Worm (Jacob Anderson) is another who adds a tormented depth to the art of yearning. He's the commander of the Unsullied, an army of warrior-eunuchs who were castrated as babies and trained to be as fearless as they are deadly on the battlefield. Despite that, his introduction to Missandei (Nathalie Emmanuel) ignites a feeling he’s never known before. He attempts to articulate it when Missandei comforts him after a near-death experience. “All men fear death,” she tells him. “Not death,” he replies. “I fear I never again see Missandei from the island of Naath.” The awesome tenderness of their relationship, despite the casual cruelty of their world, is enough to turn an observer’s knees to jelly.
Yes, Timothée Chalamet claims yet another ranking on this list. It’s not without reason. His performance as Laurie in Greta Gerwig’s beloved Little Women adaptation has him yearning for not one, but two of our little women. There is the impassioned zigzagging hill proposal to Jo (Saoirse Ronan), where he at last accepts defeat by heartbreakingly telling her he’ll just watch her fall in love with someone else if she can’t fall in love with him. There is also the plea he makes to Amy (Florence Pugh), asking her to not marry her super-rich prince, because he’s finally ready to be the man she wants him to be. So much yearning in such little women time!
How lucky are we to live in a world where we have not one, not two, not three, but four movies worth of Peeta (Josh Hutcherson) being lovelorn for Katniss (Jennifer Lawrence)? What starts as a schoolyard crush evolves into a solemn piety, one strengthened by their mutual hope for life after so much death. Even in the most trying of circumstances (a.k.a. being literal children thrown into a televised death arena), Peeta is still incredibly desperate for Katniss’s survival and well-being. His yearning for the Mockingjay is so enduring that it even overcomes the biohacking brainwashing the Capitol inflicts on him in the penultimate film (or the final book of the Suzanne Collins trilogy). As Katniss fittingly calls him, he’s our “dandelion in the spring.”
If a man dared to utter the words “I burn for you,” would you immediately fall to your knees in a Walmart parking lot, yes or no? That’s essentially what happened with Simon (Regé-Jean Page) and Daphne (Phoebe Dynevor) in Season 1 of Netflix's adaptation of Bridgerton. Simon goes from playboy to ultimate simp after he meets Daphne, the diamond of the season whom he fakes a courtship with before actually falling head over heels in love with her. The yearning goes so hard that it even spawned a viral full-length musical.
Not to be controversial, but there’s only one adaptation of the Jane Austen novel that portrays the devotion that Mr. Darcy has for Elizabeth Bennet most ardently—and it’s the 2005 version (but I still love you, Colin Firth!). Abundant are the scenes in which Matthew Macfadyen’s Darcy pines over Keira Knightley’s Elizabeth: Darcy’s iconic hand flex after scandalously holding Elizabeth’s bare hand; their near-kiss after Elizabeth fervidly rejects Darcy’s rain-drenched first proposal; how reverently Darcy looks at Elizabeth when she kisses his hand after accepting his second proposal; and, not least of all, “Mrs. Darcy, Mrs. Darcy, Mrs. Darcy.”
An honourable mention goes to Simon Woods’ Mr. Bingley, who, in one memorable scene, adoringly follows after the lovely Jane (Rosamund Pike) at a ball while fiddling with the ribbon attached to the back of her dress, like a pilgrim happening upon a holy relic.
Mr. Darcy walked so Anthony Bridgerton (Jonathan Bailey) could run.
There are many cases that justify Anthony’s spot on this list, but the only one I need to give is the steamy monologue he delivers to Kate (Simone Ashley): “Do you think that there is a corner of this earth that you could travel to far away enough to free me from this torment? I am a gentleman. My father raised me to act with honour, but that honour is hanging by a thread that grows more precarious with every moment I spend in your presence. You are the bane of my existence. And the object of all my desires. Night and day, I dream of you.”
Oh, to be the bane of my man’s existence.
These two fan-favourite Gilmore Girls boyfriends are definitely not sharing a single ranking because it saves me the impossible effort of having to painstakingly decide between the both of them … no way. In fact, the uncle and nephew duo that is Luke Danes (Scott Patterson) and Jess Mariano (Milo Ventimiglia) both deserve the third spot on this list simply because their yearning arcs mirror each other’s so acutely.
Luke harbours a decades-long, though intensely suppressed, crush on Lorelai (Lauren Graham), which at last blossoms into a real relationship after seasons worth of achingly watching her date every other guy but him. And though Jess does initially date Rory (Alexis Bledel), their electric chemistry persists post-breakup. In the revival series, Jess follows in his uncle’s footsteps by quietly keeping his longing for Rory to himself, watching her from the sidelines until, one day, she may be ready to let him back in.
Jane Austen knows how to write a perfect, pathetically-in-love man—and Johnny Flynn knows how to play him. In the 2020 adaptation, Flynn breathes new life into a swoon-worthy Mr. Knightley, who is so frustratingly in love with Anya Taylor-Joy’s Emma Woodhouse that it makes me genuinely sick.
I kid you not—after seeing this movie for the first time, I watched it again every day for probably a month straight. Burned into my brain is the scene where Knightley, overwhelmed by his epiphany of being head over heels for Emma, flees on foot. He runs homeward bound, down dirt roads in his little Regency-era capris until, at last, in the sanctuary of his solitary abbey, he strips himself and collapses anew onto the ground—a man in love.
This gem of a movie contains too many moments like the above to count. Couple that with the swelling sumptuous score, the cotton candy colour grading, and Knightley tearfully telling Emma, “I cannot make speeches. If I loved you less, then I might be able to talk about it more”—and you have your ideal yearning man.
This article originally appeared in Harper's BAZAAR US.