The best teen romance movies of all time

Director: Cameron Crowe

Cast: John Cusack, Ione Skye

Best quote: 'I gave her my heart, she gave me a pen.'

Defining moment: Y’know, the scene where John Mahoney curls into the fetal position in a bathtub is pretty underrated. Just kidding. It’s the one with the Peter Gabriel song. 

The Dobler Effect
He’s a new wave hipster with vague aspirations of becoming a professional kickboxer. She’s the school valedictorian with a great smile whose ambition has left her with no real friends. It’s a classic set-up for a mismatched young-adult romance, but Cameron Crowe packs his directorial debut with so many sharp insights and quirky details that it nearly stands outside the teen romcom genre, transcending even John Hughes and ending up closer to Annie Hall or its most obvious inspiration, The Graduate. 

Coming from one of the foremost chroniclers of restless youth, though, it exudes far more hormonal energy than either – and much less cynicism about boy-girl relationships. This is where the world fell in love with John Cusack as Lloyd Dobler, cinema’s most charming slacker, and Ione Skye is equally crushworthy as the overachieving-yet-underconfident Diane Court. (And a shoutout to Lili Taylor’s caustically lovesick Corey Flood, who certainly has her share of admirers as well.) No character is a pure archetype but complicated in the way real teens are – and while few actual teenagers in the ‘80s may have ever attempted to woo their crush by blasting a Peter Gabriel song out their window before Lloyd Dobler, certainly many took a shot after him. MS

Director: Terrence Malick

Cast: Martin Sheen, Sissy Spacek

Best quote: ‘He wanted to die with me and I dreamed of being lost forever in his arms.’

Defining moment: After killing her father, Holly and Kit burn down her childhood home, and her actual childhood along with it.

In the late 1950s, teenager Charles Starkweather and his 14-year-old girlfriend, Caril Ann Fugate, went on a killing spree, murdering 11 people across Nebraska and Wyoming before being apprehended. It was a major ‘loss of innocence’ moment for America: how could two of its own, raised in the heartland, do something so heinous, and at such a young age? The incident looms large in the country’s mythos, inspiring songs by Bruce Springsteen and Oliver Stone’s hyper-violent spectacle Natural Born Killers. It also forms the basis of Terrence Malick’s hypnotic and lyrical debut feature. Martin Sheen and Sissy Spacek are Kit and Holly – not precise avatars for Starkweather and Fugate, but clearly inspired by them – who jumpstart their life of crime by killing Holly’s father (Warren Oates) then head for the Canadian border, leaving a trail of bodies in their wake. But Malick, in what would become his signature, does not sensationalise their misdeeds, instead approaching them almost nonchalantly and not giving in to easy explanations. From Spacek’s flowery narration to the wondrous midwestern landscapes, it remains one of the most beguiling films from a director who’d eventually build a career from holding audiences in a trance. MS.

Director: Hal Ashby

Cast: Ruth Gordon, Bud Cort

Best quote: 'Oh, Harold, that's wonderful. Go and love some more.'

Defining moment: In a field of daisies overlooking a vast military cemetery, Maude explains her philosophy of life.

Age shall not wither them
The hippy era was full of movies that attempted to confront square society, to shock viewers into some undefined form of action. How many of them are still effective today? But ‘Harold and Maude’, the gentle flipside of the revolutionary dream, is every bit as charming, affecting and surprising as it must have been on its first release. Partly this is because none of its themes have gone out of date: we still live in a world of empty privilege and rigid hierarchy, petty authority and relentless conformism. So the idea of a teenage boy (Cort) shacking up with a batty old woman (Gordon) is still a challenge to social norms. Best of all, ‘Harold and Maude’ is also still devastatingly romantic: a story of soulmates, in the most literal sense. TH 

Director: Jacques Demy

Cast: Catherine Deneuve, Nino Castelnuovo

Best quote: 'People only die of love in the movies.'

Defining moment: A sad, bittersweet meeting in the snow, two lovers seeing each other for the first time in years.

All things bright and beautiful
You'd need to have a sliver of ice lodged in your heart not to be moved by ‘The Umbrellas of Cherbourg’ – a musical that has even hardened musical-haters melting into puddles. Not that it’s a musical in the belt-‘em-out tradition. Instead, every word is sung rather than spoken as 17-year-old Geneviève (Deneuve) falls sweetly and madly in love with car mechanic Guy (Castelnuovo).

‘Umbrellas’ is one of the most ravishing films ever made, wrapped in candyfloss colours to match the blush of first love. When Guy is drafted to fight in Algeria, Geneviève is certain she will die of grief. But time passes and Geneviève doesn’t die. Love fades. And that’s the bittersweet message inside this exquisitely sugar coated pill. CC

Director: Baz Luhrmann

Cast: Leonardo DiCaprio, Claire Danes

Best quote: ‘Did my heart love 'til now? Forswear its sight. For I never saw true beauty 'til this night.’

Defining moment: The doomed lovers meet cute on opposite sides of an aquarium.

All about that Baz
The first of several gaudy reinterpretations of classic literature from Baz Luhrmann, the director’s take on Shakespeare’s romantic tragedy is basically a ’90s gangster movie for theater kids. The Capulets and Montagues are competing business families in the fictional coastal town of Verona Beach whose rivalry has turned violent; Leonardo DiCaprio and Claire Danes are the young lovers caught in the middle. But it’s one thing to transfer the Bard’s iconic play to the modern world – it’s quite another to bring the original Elizabethan English with it. The linguistic poetry doesn’t quite jibe with the film’s action-movie pacing and breakneck, MTV-style editing, but it doesn’t really matter: millennials got the point just fine, and made the film into a generational lodestar.  MS

Director: Wes Anderson

Cast: Jared Gilman, Kara Hayward, Bruce Willis, Bill Murray

Best quote: 'It's possible I may wet the bed, by the way.'

Defining moment: Sam and Suzy kiss an awkward kiss on the beach.

Children, behave
Romance isn't the first thing you expect from a Wes Anderson film, but in this delightful 1960s-set tale, the American auteur employs all his usual tricks – hip soundtrack, arch dialogue, super-careful production design – in the service of a story about the chaos and madness of young love.

Sam and Suzy are 12-year-olds on the run. Suzy is precocious and independent; Sam is nerdy and serious. They don't get very far, but a mile's a long way when you're 12, and danger is never far away. What's lovely is how seriously Anderson takes Sam and Suzy's adventure, while also laying on the humour and the irony. By the time the pair steal a smooch on a deserted beach, we're totally smitten. DC

Director: Emile Ardolino

Cast: Patrick Swayze, Jennifer Grey

Best quote: ‘I'm scared of everything. I'm scared of what I saw, I'm scared of what I did, of who I am, and most of all I'm scared of walking out of this room and never feeling the rest of my whole life the way I feel when I'm with you.’

Defining moment: If there’s a better metaphor for exiting adolescence than ‘The Lift’, we ain’t seen it.

No actor could sell a goofy premise like Patrick Swayze. Whether playing the ghost of a murder victim trying to have one last shag with his wife, a bank-robbing zen-philosopher surfer, or a Catskills dance instructor from the wrong side of the tracks, he could elevate some of the silliest material to classic status through magnetism alone. Don’t get it wrong, Dirty Dancing is still plenty silly, part of a spate of movies in the ’80s about young people dancing themselves out of oppressive situations. But it’s far and away the best of those movies, owing largely to Swayze’s smooth movies, gloriously feathered mullet and eternal smoulder. Let’s not discount Jennifer Grey, though, one of cinema’s most believable girl-next-doors, who, during one memorable summer, is quite literally lifted out of teenagerdom and passed into adulthood by a hunky stranger. It was the time of her life, y’know. MS

Directors: Jerome Robbins, Robert Wise

Cast: Natalie Wood, Richard Beymer, Russ Tamblyn

Best quote: 'There’s a place for us, somewhere…'

Defining moment: It’s as camp as Christmas, but Maria (Wood) singing ‘I Feel Pretty’ while anticipating her next date with Tony (Beymer) is a magical moment of romantic exuberance.

The song of the streets
Baz Luhrmann’s Romeo + Juliet may have made all the tweeners’ hearts melt, but the real hep chicks and finger-poppin’ daddies know which version of Shakespeare’s play is the real leader of the pack.

West Side Story is like no other musical: sure, it’s sappy (‘Mariaaaaaaaaaa’) and slightly ridiculous, but it’s also brazenly political (‘if you’re all white in A-me-ri-ca!’), sneakily self-mocking (‘Hey, I got a social disease!’) and ferociously, aggressively emotional: the operatic finale is a masterclass in three-hanky audience manipulation. Also, the film contains perhaps the single best song ever written for the musical theatre: ‘Somewhere’, the ultimate romantic ballad for trapped and dreaming lovers. TH

Director: Luca Guadagnino

Cast: Armie Hammer, Timothée Chalamet, Michael Stuhlbarg, Amira Casar

Best quote: ‘Just remember, our hearts and our bodies are given to us only once, and before you know it your heart's worn out; and, as for your body, there comes a point when no one looks at it, much less wants to come near it.’

Defining moment: The peach scene. Enough said.

Summer of love
Timothée Chalamet comes of age in an Italian villa in the early 1980s in a story of sexual awakening backdropped by the sun-kissed Lombardy countryside. The future Bob Dylan is Elio, a 17-year-old transformed by a summer spent with Oliver (Armie Hammer), a 24-year-old grad student assisting his professor father with a research project. They ride bikes into town, play volleyball and eventually kiss. Then, inevitably, they depart, likely forever. Luca Guadagnino’s slowly smoldering depiction of queer discovery is sensitively handled, deeply felt and beautifully shot – it has the dreamy quality of a powerful childhood memory that’s faded at the edges but remains as vivid as the day it happened. MS

Director: Tim Burton

Cast: Johnny Depp, Winona Ryder

Best quote: Kim: 'Hold me.' Edward: 'I can’t.'

Defining moment: Kim dances in the ‘snow’ Edward makes from an ice sculpture in sunny California.

Cuts you up
The scariest thing about Burton’s gothic fairy tale is reading the list of actors who were considered for the part of Edward, the man with scissors for hands created by a scientist. The studio insisted Burton meet Tom Cruise (who believed the story needed a ‘happier ending’). Michael Jackson badly wanted the part. Tom Hanks turned it down.

Finally, Burton got his way and cast Johnny Depp, who, like a Camden goth Charlie Chaplin, plays Edward with a dash of slapstick and sad-eyed loneliness (watch Edward’s scissor fingers twitch when he’s nervous). It was the beginning of a beautiful friendship between Depp and Burton, who’ve made seven films together since. Not such a happy ending for Depp and his co-star and then-girlfriend, Ryder. They split in 1993. CC

Director: Lukas Moodyson

Cast: Rebecca Liljeberg, Alexandra Dahlström, Erica Carlson

Best quote: 'We must be out of our damn minds. But we are so fucking cool.'

Defining moment: An impulsive snog in the back of a car as Foreigner’s ‘I Want to Know What Love Is’ cranks up on the soundtrack.

I know you can show me
Romance and social transgression go hand in hand in Lukas Moodysson’s gorgeous and empathetic story of two high-school girls whose love affair scandalises the small Swedish town of Åmal. Concerns about distribution and awards probably explain why the original title – ‘Fucking Åmal’ – got changed to the cosier and less confrontational ‘Show Me Love’. But in no other area does Moodysson compromise: the emotions are raw, the romance giddy, the truths it exposes impossible to ignore. TH

Director: Tomas Alfredson

Cast: Kåre Hedebrant, Lina Leandersson

Best quote: 'If I wasn't a girl... would you like me anyway?'

Defining moment: Eli crosses the threshold to show Oskar why she needs an invite.

My bloody valentine
Vampiric love stories needn’t involve brooding, sparkling bloodsuckers and entanglements with hunky werewolves. In this Scandinavian insta-classic, vampirism is effectively a metaphor for preteen loneliness, and the emotions are as warm as the landscape is icy. In a Swedish suburb, a 12-year-old outcast named Oskar forges a strong bond with a girl named Eli who doesn’t seem to have many other friends either, for reasons that are both similar and drastically different. Director Tomas Alfredson handles the young, burgeoning romance with great sensitivity and skill, turning in something like a moody John Hughes movie that just happens to feature a whole lot of dismemberings at its climax. Trust us, it’ll make your heart swell more than your skin crawl. MS

Director: Bill Forsyth

Cast: John Gordon Sinclair, Dee Hepburn, Clare Grogan

Best quote: 'Hard work being in love, eh?'

Defining moment: Gregory (Sinclair) realises that the women in his life have all ganged up to get him into the ‘wrong’ girl’s clutches.

The beautiful game
Figuring out who we’re in love with is, of course, a key part of the romantic process. Too many films feature lightning-bolt moments, where the rightness of a match is obvious and irrevocable – cue happy ending. So it’s nice that there are a few movies out there saying, well, hang on a minute. Love at first sight is all very well, but isn’t that a rather shallow and reckless way to select a mate?

Gregory’s Girl starts with the lightning bolt – gangly Glaswegian Gregory spots leggy keepy-uppy expert Dorothy (Hepburn) – then patiently explains why, for someone as irrational and irregular as Gregory, that kind of perfect love probably won’t work. So why not try someone a little closer to home? The result is pragmatic, sure, but that doesn’t make it any less romantic. TH

Director: Nick Cassavetes

Cast: Ryan Gosling, Rachel McAdams

Best quote: ‘I think our love can do anything we want it to.’

Defining moment: That rain-soaked kiss you see above.

Sparks' notes
At this point, there is no middle ground when it comes to The Notebook. No one thinks it’s ‘pretty good,’ ‘totally fine’ or ‘just okay.’ You either think it’s cringeworthy, manipulative treacle, or it’s the greatest love story ever told, and nothing any critic could possibly write would sway your opinion in the other direction. Thus, it ends up on a list like this mostly by default. If you’re talking about cinematic romance, no movie that engenders those kinds of polarising feelings can go without mentioning, no matter how we actually feel about it. And anyway, we wouldn’t want the diehards threatening to firebomb our offices if we left it off.

We will say this, though: put aside your adult cynicism for two hours, and it’s easy to see why The Notebook has continued to resonate with generations of (mostly) teenagers. For all its cliches, it’s the only adaptation of a Nicholas Sparks novel to really stick in the public imagination, and that’s because, more than most movies, it encapsulates the idealised vision of true love only kids who haven’t yet had their hearts broken believe in. It helps that stars Ryan Gosling and Rachel McAdams fully commit to their roles, he as the simple country boy, she the young heiress whose parents forbid her to date below her station. They believe in this star-crossed affair and all its twists, turns and tragedies, and so the audience does as well. And when you get right down to it, there’s nothing wrong with that. MS

Director: Elia Kazan

Cast: Natalie Wood, Warren Beatty, Pat Hingle

Best quote: 'My pride? My pride? I don't want my pride!'

Defining moment: The young lovers break from their frenzied necking as waters symbolically cascade in the background.

Youth in revolt
Rural Kansas, 1928, when ‘nice’ girls were supposed to hold out until the wedding night. Every fibre of her being is telling high-schooler Natalie Wood she wants alpha male Warren Beatty right now, but his oil magnate dad has decided she’s too ordinary for marriage. Welcome to a world before contraception, as acclaimed playwright William Inge’s Oscar-winning script puts in place a devastating conflict between fundamental human desires and layers of obfuscating social hypocrisy.

Both in their early twenties at the time, Beatty and Wood make a sensual couple, as director Kazan constructs a pristine vision of Americana, played against a coruscating narrative where yearning slides uncontrollably into hysteria. Wood’s startling performance deserved an Oscar but got only a nomination. TJ

Director: Jason Reitman

Cast: Ellen Page, Michael Cera

Best quote: 'I still have your underwear.' 'I still have your virginity.'

Defining moment: Baby, schmaby: it’s all about Juno declaring her love for geeky Paulie Bleeker.

Que Cera, Cera
On release, first-time scriptwriter Diablo Cody’s Oscar-winning unplanned teen pregnancy comedy ‘Juno’ was all-but obscured by one debate: was it a pro-lifer tract deceptively gussied up in indie clothing?

The film’s abortion issues are still up for debate; leaving that aside for a moment, what’s left is a sweetly funny romantic comedy about relationships both teen- and middle-aged, and love of many kinds: parental, romantic and platonic. And sure, the teen-speak might bear about as much resemblance to real teenage slang as the actors in ‘Grease’ did to actual teenagers, but Ellen Page and Michael Cera’s performances remain pitch perfect. CB