The 21 Best Movie Boyfriends In Romantic Comedy History, Ranked

To all the rom-com boys we've loved before.
Behold: the best boyfriends in rom-com history.
Behold: the best boyfriends in rom-com history.

The best romantic comedies are the ones we’re willing to fight for. Welcome To HuffPost’s Rom-Com Week.

Hollywood rom-coms may be comfort viewing, but they do not portray a utopian vision of love. As a whole, they’re formulaic, lightly misogynist, heteronormative and white. They’re riddled with abusive acts framed as healthy romantic gestures. Most of the men offered to the bright-eyed female leads are either aggressively mediocre or simply aggressive. Jake Ryan of “Sixteen Candles” may have a jawline straight out of Michelangelo’s workshop, but there’s that teeny detail where he arranged his own girlfriend’s rape.

And for better or worse, these films have played a crucial role in defining the romantic predilections of, in particular, male-attracted young women for generations. Out of this primordial sludge of hucksters, stalkers, trolls and dimwits, the best and most swoonworthy of them emerged like the earliest tetrapods from which all future crushes and loves would be (spiritually) descended. In short, the rom-com boys we’ve loved before will always be with us.

Some of them, at least, we’re happy to have along for the ride. For every Jake Ryan, there’s a Peter Kavinsky; for every Joe Fox, there’s a Matt Flamhaff. Here and there, sprinkled throughout the rom-com canon, we find a man so ridiculously good-hearted and good-looking that we’d happily relive ages 13 to 30 with him.

In honor of HuffPost’s Rom-Com Week, some of our most avid rom-com fans ranked their fantasy movie boyfriends and reflected on just what, exactly, made these lads worthy of our devotion.

21. Michael Moscovitz (Robert Schwartzman) in “The Princess Diaries”

Just as Peter Kavinsky did for lax bros, Michael Moscovitz embodied a classic fantasy stripped of all its intimidation to make it more comfortable to adolescent girls. He plays in a garage rock band; he fixes cars; he has dangerously alluring sideburns. It would all be almost too much edgy masculine energy were he not so slight and shy, so reserved that his younger sister’s best friend, Mia (Anne Hathaway), doesn’t even notice that he adores her. Also, he loves M&Ms ― not sure what that says about his character, but I guess that he’s not afraid to enjoy the sweeter things in life. Michael is delicately handsome, multitalented and soulful, but he’s not a conceited prick about it. All he wants is one special girl to come to his band Flypaper’s rehearsals and get free car maintenance from his own loving hands. No disrespect to Mia and her truly embarrassing crush on status hound Josh Bryant, but I would have seen Michael when he was invisible. Claire Fallon

20. Westley (Cary Elwes) in “The Princess Bride”

Westley knows when to take charge (like when you’re trying to survive the Fire Swamp and battling Rodents of Unusual Size) and when to listen to the strong and independent woman in his life. Plus, he has the whole charming blonde farm boy-turned-sword-fighting-pirate thing going on. “As you wish” is a romantic line for the ages, instilling in women around the world the fantasy of simply ordering a man around and having him love her even more for it. ―Emma Gray

19. Graham Simpkins (Jude Law) in “The Holiday”

There are many reasons Graham Simpkins is crushable: He’s charmingly British, he’s got a humble but intriguing job as a book editor, he lives in the coziest English countryside home, and he’s handsome as hell. But it’s his love for his family that makes him completely swoonworthy. His obvious affection and devotion to his two painfully adorable daughters is enough to induce happy tears. Who doesn’t melt when he finally relents and does Mr. Napkin Head, resulting in a fit of giggles from both his kids and Amanda? Graham alone is dreamy, but he and his girls ― the Three Musketeers ― are a complete rom-com package. ―Paige Lavender

18. Edward Lewis (Richard Gere) in “Pretty Woman”

My mom and I have very different tastes when it comes to, well, almost everything. Except, that is, for the ’90s sex god that is Richard Gere, the ultimate mom crush who also makes their offspring sprung. In “Pretty Woman,” Gere plays Edward Lewis, a wealthy businessman who’s gone all the way (in school guys, come on!). His face looks like a hot almond come to life. With his gray hair and dolphinesque bare chest, Lewis embodies the hottest parts of boyhood and manhood. And like the decidedly less sexy Jack Donaghy, he knows there’s no bad time to rock a tux. Sure, he bargains down the price for a cash-strapped sex worker to pose as his girlfriend, which is a hugely dick move. But, he would have paid $4,000, which is... sweet, I guess? Priscilla Frank

17. Lloyd Dobler (John Cusack) in “Say Anything...”

They say he ruined men for a whole generation of women. I cannot speak to this, but I can tell you about all the teenage boys who ruined themselves in the name of Lloyd Dobler. I’m talking about the guys who agonized over the transitions in their mixtapes, who spent a year pretending to like The Replacements, who wore pork pie hats or trench coats or some other accessory that in high school betokened a charmingly out-of-step sense of personal style but which did not last 15 minutes past college orientation. I’m talking about the guys who thought love was something to be won, and won at that with a series of gestures. I’m talking especially about the guys who went a little too readily for the grand gesture and wound up, I dunno, incels or something. Cameron Crowe, the director, has said of Lloyd that he is a monument to the idea of “optimism as a revolutionary act.” I like that. If you’re a teenage boy, it is easy to watch “Say Anything…” and not see that this is why Diane Court falls for Lloyd Dobler. It’s not the gestures themselves, not ultimately. It’s the optimism underlying them. It’s not the boombox. It’s the hope that impelled him toward her window in the first place. ―Tommy Craggs

16. Jake Perry (Josh Lucas) in “Sweet Home Alabama”

If I had to point to one cinematic moment that defined my adult sexuality, it would be the moment in “Sweet Home Alabama” when Jake (Josh Lucas) closes the door on his estranged wife, Melanie (Reese Witherspoon), who has just arrived back to ask for a divorce. “Jake!” she shrieks as he turns away. “You dumb, stubborn, redneck hick!” I had to rewatch the scene just now to catch the line, because all I ever notice is poor Jake’s face as he absorbs this cruel attack, his brow spasming into tortured furrows, his usually lively eyes bottomless pits of hurt. “This is a man who loves a woman enough to be wounded by her,” I thought, with a romantic sigh. OK, it’s not healthy! But it’s a reversal of a common rom-com trope, in which the woman is wounded because she loves someone who isn’t careful with her, and seeing that vulnerability from a man is seductive.

Jake loses points for not giving his wife a divorce, after years of estrangement, because he wants to win her back. Manipulative, bad, wrong. But he worked hard to be someone who could make her happy, who could fit into both sides of her life ― her Southern country roots and her artsy city ambitions ― all while, incidentally, being mouthwatering in that particular dirt-smudged, rumpled way. Claire Fallon

15. Mr. Darcy (Matthew Macfadyen) in “Pride and Prejudice”

Mr. Darcy is such an exquisite rom-com boyfriend that not even Matthew Macfadyen’s performance as a deranged hanger-on in my favorite show of the year, “Succession,” could sour my taste for him. Sure, Fitzwilliam is, in early courtship with Elizabeth Bennet, a bit of a dick. He’s proud, I get it. But I’m a sucker for a guy whose discerning approach to human interactions casts them as universally misunderstood by people who are unwilling to play a little social badminton. He appears to be this big bad rich dude who believes Elizabeth’s piddly landowning family is beneath him. But, oh, what assholes we are to assume as much. When I rewatch this movie, six to seven times a year, I want so desperately to skip to the end to watch Keira Knightley’s aha moment, but I don’t. Because the cinematic anticipation is incredible! I know Matthew Macfadyen will inevitably wobble out into the field with his shirt half-fastened and his hair splashed across his forehead all sexy like. If it’s wrong to want a man who hates literally everyone else but somehow finds something admirable in me, I don’t want to be right. (Also, I don’t care about Colin Firth.) Katherine Brooks

14. Benjamin Barry (Matthew McConaughey) in “How to Lose a Guy in 10 Days”

Oh, Benny boo boo boo boo boo boo boo! Of Matthew McConaughey’s rom-com star turns, Benjamin Barry is indisputably the sexiest, the one that allows him to relax into his drawl and his lazy grin and his rippling muscles. (Remember how “The Wedding Planner” tried to make him a nerdy doctor with a pair of glasses and a wardrobe of khakis? Lol.) Ben is also such a craven turd of a human being that he’s only redeemable because Andie is also dreadful ― and yet, he’s still worse. She’s just trying to torture a guy for 10 days; he’s trying to get a woman on the hook for a much longer emotional involvement by making her fall in love with him so he can get a promotion. Ben is the guy we keep texting against our better judgment, reading the best of intentions into him preventing us from getting to a job interview in D.C. or ― well, that’s the only romantic gesture he makes that isn’t professionally motivated in the whole movie ― because he’s just so fit, so confident, so charming. —Claire Fallon

13. Charles (Hugh Grant) in “Four Weddings and a Funeral”

If this movie proves anything it’s that handsome men are often even more handsome when they put on glasses. As far as I’m concerned, most men should wear glasses whenever possible, whether or not they actually have impaired vision. But beyond his attractive accessorizing, Charles has a sweet and bumbling charm. He’s basically a slightly younger William Thacker, similarly desperately in love with the film’s token American (Andie MacDowell). He loses a few points for screwing over another woman in the process, but I still can’t stop myself from falling for his British accent, wavy hair and ultimate romantic gesture of not insisting the woman he loves marry him. ― Emma Gray

12. Matt Flamhaff (Mark Ruffalo) in “13 Going on 30”

Sometimes nerdy boys grow up to be vindictive misogynists who believe women are out to get them. But every once in a while, they will flower into sensitive, grounded and super hot men. Case in point: Matt “Matty” Flamhaff, Mark Ruffalo’s character in “13 Going on 30.” He knows the dance moves to “Thriller,” builds fantasy dollhouses, wears CBGB T-shirts and has Mark Ruffalo’s face. Would spend hours in a closet with (adult) Matty any day. ―Priscilla Frank

11. Jack Callaghan (Bill Pullman) in “While You Were Sleeping”

First, Google image search “Bill Pullman” plus “While You Were Sleeping.” Gaze upon that normcore get-up, that wrinkled khaki, that flannel. Look at that side part, that smirk he’s giving as he stares up at you, YOU, from a stairwell somewhere. In the first rom-com involving a coma on this list, Jack’s appeal is quiet at first, but it’s elevated by the smoking hot chemistry he and Lucy (Sandra Bullock) have. (He doesn’t know if he wants to hug the woman brazenly pretending to be his comatose brother’s fiancé or arm-wrestle her, but he should probably arm-wrestle her because she’s certainly lying!) Now let yourself remember the proposal scene, when, after this entire family saga has unfolded and Jack’s very astute skepticism has been validated by Lucy’s confession that she is NOT the fiancé of his formerly comatose brother, he slips an engagement ring into the token tray at Sandra Bullock’s Chicago Transit Authority job and asks her to marry him in front of all his relatives and a smattering of the quaintest commuters you’ve ever seen. Bill Pullman ascended to his throne in the rom-com boyfriend pantheon right then. ―Katherine Brooks

10. Kumail (Kumail Nanjiani) in “The Big Sick”

Kumail, played by comedian Kumail Nanjiani, is probably the most realistic and therefore the actual best rom-com boyfriend on this list. The character is based on Nanjiani, who waited by his then-casual-girlfriend’s side after she fell into a mysterious coma, contributed to her life-saving diagnosis, tolerated Ray Romano’s infidelity guilt jokes and somehow avoided pulling a “The Graduate” with Holly Hunter. Those last parts are fictional, but come on. In a slight twist of tropes, the movie is told largely from the boyfriend’s perspective ― a single guy with traditional Muslim parents whose life is relatively uneventful until he falls for a white woman. In the process of figuring out his feelings for a comatose woman (this is the second rom-com on this list involving a comatose love interest, huh?) and reconciling his worldview with that of his mom and dad, he doles out both the polished rejoinders and effusive soliloquies we expect from the best rom-com leading men. And that Hugh Grant hair! ―Katherine Brooks

9. Patrick Verona (Heath Ledger) in “10 Things I Hate About You”

Those luscious curls, that Aussie accent, those goddamn dimples, the way he perches a toothpick between his lips like you could be that toothpick. Heath Ledger’s Patrick Verona in “10 Things I Hate About You” is the ultimate underage rebel with a mushy heart. Sure, he started out courting Kat as a way to make some extra cash, but if you’ll refer to my earlier point, DIMPLES. ―Priscilla Frank

8. Josh Lucas (Paul Rudd) in “Clueless”

Would you fuck your ex-stepbrother? If that stepbrother were Josh Lucas, my answer would be: maybe! Paul Rudd’s insanely likable, flannel-wearing college bro in “Clueless” made mainstream America think incest was chill. Josh dances like a balloon man at a car dealership, reads Nietzsche, cares about current events, and will tease you and take care of you in equal measure. No wonder he has Cher totally “butt crazy.” ―Priscilla Frank

7. Cliff Pantone (Jesse Bradford) in “Bring It On”

Some might argue that “Bring It On” isn’t even a rom-com, and it’s thanks to Jesse Bradford as Cliff Pantone and his blistering chemistry with Kirsten Dunst’s Torrance Shipman that we disagree. In pitch-perfect teen boy fashion, Cliff wobbles back and forth between almost sneering confidence and goofy playfulness. He’s some vague sort of pop-punk indie kid to her head cheerleader, and their blossoming flirtation opens them both to worlds that they once held in rigid contempt ― a fantasy, to be introduced to a genre of music by a man with Cliff’s bold, smirking eyebrows and impeccably brushed white chompers. Several of their joint scenes are among the PG-hottest in the history of cinema. Not just the side-by-side toothbrushing, but the heated, knowing grin he shoots at her when he realizes she’s been watching him flail around his room shredding his guitar, and that almost-kiss on the swings. Cliff, baby, you’re just what we need. ―Claire Fallon

6. Harry Burns (Billy Crystal) in “When Harry Met Sally...”

I’m not the first person to point out that Harry Burns and Sally Albright are two versions of Nora Ephron, one heartburned and mordantly wised-up, the other doe-eyed and sunnily optimistic. Ephron wrote the script, and in her hands the love story isn’t a pursuit so much as a deepening of feeling between two people as each realizes there is much of the one contained within the other. Harry doesn’t make this list without Sally. That’s the loveliness of “When Harry Met Sally…” Other men in the lineup, Will Thacker and Josh Lucas and Mark Darcy, you could parachute into any other rom-com and they’d find a way back to your heart. Take Harry out of this one and he’s no one’s beau ideal. He’s a simpering hornball political consultant, a hound who hides it with a pervading yuppie glibness; he will no doubt spend the ’90s getting Rudy Giuliani elected mayor. Harry becomes charming only when you notice the parts of him humming in sympathetic resonance with Sally. That’s what makes him a different sort of rom-com crush. You love him for the humming. You love him for the love. ―Tommy Craggs

5. Max (Jake Lacy) “Obvious Child”

Never have Crocs looked finer than on the trotters of Max, the dopey-cute bro who woos Jenny Slate’s Donna in an abortion rom-com that felt, four years ago, like the most delightfully explosive addition to a genre that deigns to cater to female audiences, but can easily run amok when Nora Ephron isn’t helming the movie. Jake Lacy, the actor who plays Max, possesses one of those smiles that cracks across the face gradually and when it finally lands, buckles all knees in the general vicinity. But more than his perfectly sculpted butt chin, Max has a kind of personality trait that is historically undervalued in fictional fairy tales: he’s [insert heart eyes emoji] harmless. And I don’t mean he can’t take a guy in a fight. I’m sure, if given the opportunity, he could take a guy in a fight. No, Max wins top honors in the rom-com boyfriend ranking because he doesn’t hurt Donna. Donna hurts Max (after she hurts herself in the process of navigating the minefield that is being a sexually active woman in a world that doesn’t love sexually active women), but Max never hurts her. Even in the end, when you think his good-guy schtick is running thin, there he is ― showing up. He is not the enemy, not once in this movie. What a fantasy, indeed. ―Katherine Brooks

4. Nick Young (Henry Golding) in “Crazy Rich Asians”

Who is Nick Young? A Singaporean celebrity with a helluva trust fund. A romantic gentleman with a humana-humana six-pack and darling accent. A nonchalant heir who forgets to tell his girlfriend about his family’s billions until she’s reclining her first class seat all the way into a bed. The “Crazy Rich Asians” lead, played by perfect specimen Henry Golding, is less of a human than a nebulous, romantic fantasy ― handsome and rich, loves his mama but not as much as his girlfriend. But unlike fellow fictional billionaire Christian Grey, Young is an uncomplicated good guy who is actually worth your valuable daydreaming time. ―Priscilla Frank

3. Mark Darcy (Colin Firth) in “Bridget Jones’s Diary”

Mark Darcy is Mr. Darcy from “Pride and Prejudice” but better, because he’s a modern-day barrister rather than a stuffy member of the landed gentry. We challenge anyone not to be taken in by Colin Firth’s sad eyes and goofy reindeer sweater and valiant attempt at physical combat. Plus, isn’t it the ultimate (and also simplest) dream to find someone who “likes you very much, just as you are”? ―Emma Gray

2. William “Will” Thacker (Hugh Grant) in “Notting Hill”

William Thacker is appealing, in part because he is a man imagined to be as insecure and self-doubting in his relationships as we are used to seeing women depicted to be. He stumbles over his words and shows up with flowers at the wrong time and tells Anna (Julia Roberts) that she’s “heavenly,” and has a quirky job at a quirky travel bookshop. Plus, just look at him. He has floppy hair that somehow looks good no matter how bed-heady it gets, bright blue eyes and a touch of melancholy that permeates his entire personality, making him more approachable than your average dreamboat. And he’s played by Hugh Grant, an actor so inexplicably charming that he was typecast as the perpetual sweet romantic lead, despite a well-documented history of being a cad IRL. He’s just a boy, standing in front of a girl, eventually admitting he loves her. ―Emma Gray

1. Peter Kavinsky (Noah Centineo) in “To All the Boys I’ve Loved Before”

Putting Peter Kavinsky at No. 1, just months after he ruined all our teenage memories in “To All the Boys I’ve Loved Before,” might hint that HuffPost boy-crushers are falling prey to recency bias.

But it’s utterly scientific. If I were to design a personal value rubric for male rom-com leads (like, say, right now), I would score them on the following: hotness, sex appeal (it’s different!), essential kindness, humor, and how much he is obsessed with his romantic counterpart. As the oceans of pixels I’ve already devoted to Peter K. attest, I give him full marks. The first two are self-evident ― the sleekly tousled dark hair, the loose-limbed athleticism, the nose-crinkling grin ― but it’s in the latter three that he really shines. He’s the lax bro who isn’t setting you up for a prank by asking you to homecoming. He doesn’t want to change you, with a makeover or otherwise, in service of his own social status. He’s coping with emotional trauma from his dad abandoning the family, but he doesn’t need a manic pixie dream girl to fix him either.

Even more than sweet, shy Lara Jean, he understands that relationships are give and take, and he’s willing to give. Specifically, as evidenced by his yearning, awestruck eyes, he’s willing to give to her. What (appropriately aged) person wouldn’t accept a Yakult from a beautiful boy with what Jesse McCartney would call a “beautiful soul”? In Peter K.’s hands, our love would never go to waste.Claire Fallon

Our runners-up, in no particular order:

Jake Ryan (Michael Schoeffling) in “Sixteen Candles”

Chase Hammond (Adrian Grenier) in “Drive Me Crazy”

C.K. Dexter Haven (Cary Grant) in “The Philadelphia Story”

Troy (Ethan Hawke) in “Reality Bites”

Eddie (Matthew McConaughey) in “The Wedding Planner”

Sam Coulson (Michael Vartan) in “Never Been Kissed”

Walter Burns (Cary Grant) in “His Girl Friday”

Sam Baldwin (Tom Hanks) in “Sleepless in Seattle”

Johnny Castle (Patrick Swayze) in “Dirty Dancing”

Jack Trainer (Harrison Ford) in “Working Girl”

Joe Fox (Tom Hanks) in “You’ve Got Mail”

Jonathan Trager (John Cusack) in “Serendipity”

Joe (Jonathan Rhys Meyers) in “Bend It Like Beckham”

Dr. David Huxley (Cary Grant) in “Bringing Up Baby”

Demetrius (Christian Bale) in “A Midsummer Night’s Dream”

Will Freeman (Hugh Grant) in “About a Boy”

Robbie Hart (Adam Sandler) in “The Wedding Singer”

Nino Quincampoix (Mathieu Kassovitz) in “Amelie”

Lance Sullivan (Morris Chestnut) in “The Best Man Holiday”

Benny (Aidan Quinn) in “Benny & Joon”

Nicholas Devereaux (Chris Pine) in “The Princess Diaries 2”

Aaron Altman (Albert Brooks) in “Broadcast News”

Preston Meyers (Ethan Embry) in “Can’t Hardly Wait”

Peter Bretter (Jason Segel) in “Forgetting Sarah Marshall”

Ronny (Nicolas Cage) in “Moonstruck”

Michael O’Neal (Dermot Mulroney) in “My Best Friend’s Wedding”

William Shakespeare (Joseph Fiennes) in “Shakespeare in Love”

Paul Tannek (Jason Biggs) in “Loser”

Jeff Daly (Mark Ruffalo) in “Rumor Has It”

Jerry Maguire (Tom Cruise) in “Jerry Maguire”

Tom Hansen (Joseph Gordon-Levitt) in “(500) Days of Summer”

Johnny Martin (James McAvoy) in “Penelope”

Kevin Malcolm Doyle (James Marsden) in “27 Dresses”

Phil Connors (Bill Murray) in “Groundhog Day”

Jonathan Switcher (Andrew McCarthy) in “Mannequin”

Rob Gordon (John Cusack) in “High Fidelity”

Prince Akeem (Eddie Murphy) in “Coming to America”

Dominic (Michael Ealy) in “Think Like a Man”

Keith Nelson (Eric Stoltz) in “Some Kind of Wonderful”

Jesse (Ethan Hawke) in “Before Sunset”

Leopold (Hugh Jackman) in “Kate & Leopold”

Jason (Boris Kodjoe) in “Love & Basketball”

Andrew Paxton (Ryan Reynolds) in “The Proposal”

Jamie (Colin Firth) in “Love Actually”

Alex Sheldon (Luke Wilson) in “Alex & Emma”

Eddie Thomas (John Cusack) in “America’s Sweethearts”

Joe Bradley (Gregory Peck) in “Roman Holiday”

Patrizio “Pat” Solitano (Bradley Cooper) in “Silver Linings Playbook”

Jason (Zac Efron) in “That Awkward Moment”

Kevin O’Donnell (Adam Garcia) in “Coyote Ugly”

Dr. Aaron Conners (Bill Hader) in “Trainwreck”

Randy (Nicolas Cage) in “Valley Girl”

George Knightley (Jeremy Northam) in “Emma”

Benjamin Braddock (Dustin Hoffman) in “The Graduate”

Michael Carrington (Maxwell Caulfield) in “Grease 2”

Allen Bauer (Tom Hanks) in “Splash”

Nick Marshall (Mel Gibson) in “What Women Want”

Martin Q. Blank (John Cusack) in “Grosse Point Blank”

Charlie Lang (Nicolas Cage) in “It Could Happen to You”

Philip F. “Duckie” Dale (Jon Cryer) in “Pretty in Pink”

Harold Parker Chasen (Bud Cort) in “Harold and Maude”

Melvin Udall (Jack Nicholson) and Simon Bishop (Greg Kinnear) In “As Good as It Gets”

Rabbi Jake (Ben Stiller) and Father Brian (Ed Norton) in “Keeping the Faith”

Steve Brady (David Eigenberg) and Big (Chris Noth) in “Sex and the City”

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