The 36 best romantic movies to watch on Valentine's Day 2020

Telegraph reporters
·21 min read
best romantic movies to watch on Valentine's Day 2020 - Film Stills
best romantic movies to watch on Valentine's Day 2020 - Film Stills

Valentine’s Day 2020 is here, when love makes the world go round (and gets box-office tills ringing).

But if you’re planning on having a night in this year, and you’re stuck for a film to watch, here are our top 36 romantic movie suggestions.

Do you agree with our choices? Add yours in the comments below…

1. Brief Encounter (1945)

Parting has never been such sweet sorrow as in David Lean’s adaptation of a Noël Coward play. Celia Johnson is Laura Jesson, the suburban housewife married to a crossword-fixated man; she falls in love with a dashing medic called Alec (Trevor Howard), and the rest is – repression. It’s almost unbearable to watch Laura strain against her suburban self, trying to convince herself that she has a right to lunge for happiness. “This can’t last. This misery can’t last,” she cries. 

Best moment: As Alec leaves Laura in the train station, he puts his hand on her shoulder; in that gesture there are fathomless depths of gratitude, tenderness, longing and regret.

2. Casablanca (1942)

“You must remember this…” could stand as a motto for this golden-age Hollywood triumph, an immersive tale of wartime intrigue and thwarted amour. Bogart and Bergman are beyond compare, and the happy-accident screenplay collaboration is the stuff of legend.

Humphrey Bogart and Ingrid Bergman in Casablanca (1942) - Corbis Historical
Humphrey Bogart and Ingrid Bergman in Casablanca (1942) - Corbis Historical

Best moment: Simply the most memorable farewell in the history of farewells. “Inside of us, we both know you belong with Victor… If that plane leaves the ground and you’re not with him, you’ll regret it. Maybe not today. Maybe not tomorrow, but soon, and for the rest of your life…”

3. Roman Holiday (1953)

From the moment we see crown princess Ann (Audrey Hepburn) toying with her shoes under her voluminous dress, we know she’s bored with the regal lifestyle. Naturally, only one profession could provide someone dashing enough for her: journalism. And so it’s into the arms of foreign correspondent Gregory Peck that she falls. William Wyler directs this sublime couple with infinite charm.

Best moment: Peck pretends that his hand has been bitten off by an ancient stone face. Hepburn’s initial panic, and the way they hold and gaze at each other afterwards, radiate pure, unscripted affection.

4. Jules et Jim (1962)

Three isn’t a crowd in François Truffaut’s wonderful adaptation of Henri-Pierre Roché’s novel. Henri Serre and Oskar Werner are two friends who are equally smitten by Jeanne Moreau, an exuberant free spirit whose vagrant character they find encapsulated by a phrase in a novel: “On a ship, a woman made love to a stranger in her mind.” The camerawork on this New Wave classic is as ecstatic and giddying as falling in love itself. Truffaut moves between comedy and tragedy with remarkable ease.

Oskar Werner and Jeanne Moreau in Jules et Jim (1962) - Film Stills
Oskar Werner and Jeanne Moreau in Jules et Jim (1962) - Film Stills

Best moment: Moreau, baggy-jumpered and sporting a moustache, races across a bridge with Jules and Jim.

5. Gregory’s Girl (1980)

When the voluptuous Dorothy (Dee Hepburn) joins the school soccer team, tongues start wagging, hormones surge out of control, and love blossoms in the damp and sweaty changing rooms. But is she really Gregory’s girl? Bill Forsyth’s delightful comedy, set in an ultra-average new-town comprehensive and starring the gloriously gawky John Gordon Sinclair, captures the exquisite agony of teenage infatuation with unerring affection.

Best moment: Gregory, bamboozled into a date with the far more suitable Susan (Clare Grogan), “explains” gravity as they dance horizontally in the park at sunset, warning her: “Don't stop, or you’ll fall off.”

6. It Happened One Night (1934)

Famously causing a drop in vest sales when Clark Gable revealed a bare chest, this Frank Capra comedy is one of only three films to take the top five Oscars – for Best Picture, Director, Screenplay, Actor and Actress. It combines a magical innocence of tone with a risqué plot, as married rich girl Ellie (Claudette Colbert), on the run from a disapproving father, hooks up with Gable’s resourceful journalist Peter on the night bus to New York. As they cross the country, sleeping in motels and haystacks, contempt becomes love, and the walls of Jericho – the sheet on a rope that has divided their beds – come tumbling down.

Best moment: Ellie, tear-stained and wide-eyed, appears from behind the sheet to declare: “Take me with you, Peter. I can’t let you go out of my life now. I cannot live without you.”

7. La La Land (2016)

This gorgeous hit proves that a boy, a girl and a Los Angeles sunrise are still capable of working their magic. The boy is Sebastian (Ryan Gosling), a passionate jazz pianist with a half-formed but wholehearted ambition to open a club of his own and defend his favourite music from extinction. And the girl is Mia (Emma Stone), a gifted aspiring actress who flits between fruitless auditions and a coffee-shop till on the Warner Bros studio lot. All that each of them needs is an opportunity. What they find is each other.

Best moment: Upbeat: Mia and Sebastian dance upon air at the Griffith Observatory; downbeat: the quiet smile that they share years later as they part for the very last time.

8. The Philadelphia Story (1940)

Never has class war seemed more elegant and, well, classy, than in George Cukor’s version of Philip Barry’s comedy. Everything about it is so darned stylish that it could end up as brittle as its heiress heroine (Katharine Hepburn at her most luminous). Its great heart springs from the fact that she learns to love the right man (ex-husband Cary Grant) by kissing the wrong one (James Stewart’s love-struck journalist).

Best moment: “Put me in your pocket, Mike”: Hepburn’s husky request to Stewart as he sweeps her into the darkness.

9. Solaris (2002)

Steven Soderbergh’s sombre meditation on love and loss has an almost unbearable intensity: although it’s set largely in the vastness of space, it’s one of the most emotionally claustrophobic films there is. George Clooney plays Kelvin, a shrink sent to a distant space station after the planet it orbits starts to play terrifying games with the minds of the crew. Kelvin discovers that he isn’t immune when his dead wife materialises beside him in bed.

Best moment: At the deeply ambiguous conclusion, Kelvin asks, bewildered, “Am I alive or dead?”, to which his wife replies: “We don’t have to think like that any more.”

10. The Graduate (1967)

“Elaine! Elaine! Elaine!” It’s the interrupted wedding scene to end them all. Dustin Hoffman’s screams to bride Katharine Ross are racked with a desperation that borders on mania. And it’s not just romantic fluff. The lost dream of the late Sixties, the battle of cynical middle-age against youthful idealism, the timeless appeal of a bright red Alfa Spider – they’re all bound up in this peerless finale to a lyrical and life-affirming film. “It’s too late,” smiles her mother, Mrs Robinson (Anne Bancroft). “Not for me,” says Elaine. Exit the lovers on an unforgettable bus-ride to ambiguity.

Katharine Ross and Dustin Hoffman in The Graduate (1967) - Film Stills
Katharine Ross and Dustin Hoffman in The Graduate (1967) - Film Stills

Best moment: Simon and Garfunkel singing “Are you going to Scarborough Fair?”

11. An Officer and a Gentleman (1982)

Yes, Richard Gere is an officer, yes, he’s a gentleman, but above all he’s a lover. John Travolta turned down the role of the ne’er-do-well trainee fighter pilot redeemed by Debra Winger, and good thing too. He lacks the hardness that we have to see the character shedding, wouldn’t have cut such a dash as Gere in his white outfit, and would have been effortlessly outshone in the looks department by his smouldering belle.

Best moment: Winger is in her dismal factory; Gere, in full dress uniform, strides in and sweeps her off her feet. It’s the definitive romantic image.

12. Love Story (1970)

Cancer and ice-hockey: not, on paper, a recipe for romance. But throw in Ali McGraw, a lush Oscar-winning score and some chunky early-Seventies woollens, and you have the highest-grossing film of the year. “What can you say about a 25-year-old girl who died?” asks sportif rich boy Ryan O’Neil in the opening line. Plenty, of course, most of it schmaltzy but irresistible. Poor-girl McGraw succumbs to terminal illness while coining the phrase “Love means never having to say you’re sorry.” It’s the music that really gets you.

Best moment: The carefree snowball fight of the doomed lovers.

13. The Shape of Water (2017)

Elisa (Sally Hawkins) is a mute who lives alone and works nights at the Occam Aerospace Research Centre. When she develops an odd relationship with The Asset (Doug Jones), an amphibious humanoid creature being studied by the government, she’s determined to free him. Hawkins radiates emotional intensity; it’s all very strange and beautiful, even by Guillermo del Toro’s high standards.

Best moment: The exchange of glances through the hazy glass of The Asset’s tank.

14. The Artist (2011)

Michel Hazanavicius’s silent film isn’t just a story about love, but a love letter to the cinema itself. It centres on the love between an established film star, George (Jean Dujardin), and a beguiling actress, Peppy (Bérénice Bejo), during the rise of the talkies in Hollywood. Drained of noise and colour, it might just be a series of moving pictures, but pictures have seldom been as moving as this.

Best moment: Peppy visits a hospitalised George, and unrolls the film he’s rescued from a house fire: the footage shows the first scene the pair shot together before their career trajectories diverged.

15. Gone with the Wind (1939)

With the American Civil War as an expansive backdrop, and enough famous set-pieces to win eight Oscars, this epic is still a simple love story at heart, though arguably it’s more about the power of sex than the mysteries of love. Vivien Leigh’s petulant Scarlett O’Hara is a terrible pain, but Clark Gable’s Rhett Butler is besotted, witty and wise enough to make his kicking down of the bedroom door an act of passion rather than brutality.

Best moment: Rhett to Scarlett as they kiss and she says she’ll faint: “I want you to faint. This is what you were meant for.”

16. In the Mood for Love (2000)

Like so many great romances, Wong Kar-Wai’s modern Hong Kong masterpiece is about the impossibility of a romance. It overflows with sensuality and passion, but the man and woman at its heart (Tony Leung and Maggie Cheung) never consummate their love. They’re both married, and are drawn together only when they discover that their partners are having an affair with each other. Soundtracked by the aching cries of cellos in the night, drenched in super-saturated tones, this is the ultimate in desire and frustration.

Tony Leung and Maggie Cheung in In the Mood for Love (2000) - Film Stills
Tony Leung and Maggie Cheung in In the Mood for Love (2000) - Film Stills

Best moment: Tony Leung whispers his most secret thoughts into a hole in the ruined temple of Angkor Wat.

17. Sunrise (1927)

Many silent classics tend to be admired from a reverential distance, but not FW Murnau’s Sunrise: it’s impossible not to respond to it as if were made only yesterday. Led astray by a lascivious “woman from the city”, George O’Brien plots to kill his unsuspecting wife (the luminous Janet Gaynor), only to see the light in a series of reconciliation scenes as tender as they are uplifting.

Best moment: O’Brien and Gaynor go to a photographer’s studio and act like giggling newlyweds all over again.

18. La Belle et la Bête (1946)

The film may be based on the classic fairy tale, but Jean Cocteau transforms it into a heartstopping examination of sexual and romantic love. Jean Marais as the Beast is a real animal, clawing at Belle’s door at night and drinking the blood of his prey. Josette Day’s delicate heroine is terrified and disgusted by this high-testosterone monster, but comes to love the Beast’s gentle, self-sacrificing soul. It’s deeply Freudian, but oh-so-moving.

Best moment: Belle offers the Beast some water in her hands, and he laps it like a cat.

19. Dirty Dancing (1987)

A generation of teenage girls were obsessed with this Emile Ardolino film. It’s the ultimate female adolescent romance: smart-but-plain daddy’s girl (Jennifer Grey’s “Baby”) has her sexual – and rhythmic – awakening with a chiselled resort dance teacher (Patrick Swayze’s Johnny). It’s 1963 and, away from the family activities, Baby is mesmerised by a below-stairs world where the staff bump, grind and lose themselves in sensuous R&B rhythms. Baby saves Johnny from a lack of self-worth; he saves her from the foxtrot.

Best moment: “Nobody puts Baby in a corner,” says Johnny, and leads her on stage for the dance of her life.

20. An Affair to Remember (1957)

This is the film that Meg Ryan keeps talking about in Sleepless in Seattle. Cary Grant is a carefree playboy who falls in love with Deborah Kerr, a nightclub singer engaged to a wealthy businessman, and vows to meet her six months later at the top of the Empire State Building. Shot in lush Cinemascope, it looks sumptuous and features some of the most romantic lines ever written. As Kerr sighs: “Winter must be cold for those with no warm memories.” Grant was rarely this sad or soulful again.

Best moment: Kerr tells Grant, “I was looking up. It was the nearest thing to heaven. You were there.”

21. The Way We Were (1973)

It’s a case of opposites attracting, as impoverished communist student Katie (Barbra Streisand) falls for rich jock Hubbell (Robert Redford at his most gorgeous). But he hardly knows she exists until a chance meeting years later. They fall in love and for a brief honeymoon period, life is filled with long walks on the beach, before their different views drive them apart. All they’re left with are “misty watercoloured memories of the way we were”.

Best moment: Hubbell turns up drunk to Katie’s romantic meal and falls asleep. But he does so beautifully.

22. The Fault in Our Stars (2014)

Josh Boone’s film is adapted from the phenomenally successful young-adult novel by John Green. It’s about Augustus and Hazel, two American teenagers who’re both diagnosed with terminal cancer and bond over their search for a mysterious novelist (Willem Dafoe). It’s tenderly performed, by Shailene Woodley in particular, and our leading pair have plenty of melancholy spark.

Ansel Elgort and Shailene Woodley in The Fault in Our Stars (2014) - James Bridges/AP
Ansel Elgort and Shailene Woodley in The Fault in Our Stars (2014) - James Bridges/AP

Best moment: Augustus’ posthumous eulogy for Hazel: “Hazel knows the truth. She didn’t want a million admirers; she just wanted one. And she got it. Maybe she wasn’t loved widely, but she was loved deeply. And isn’t that more than most of us get?”

23. Laura (1944)

Unusually for a romance, the heroine is dead when the hero falls in love with her. Laura (Gene Tierney) has been murdered, and tough cop Mark McPherson (Dana Andrews) is interviewing two of the men who loved her. He becomes smitten by the sweetness they describe, and also by the portrait above her fireplace. Then she comes back from the dead. Part-thriller, part-romance, with plenty of sharp humour thrown in and a wonderful David Raksin score, Otto Preminger’s film is near-perfect.

Best moment: It’s late at night and McPherson has fallen asleep drunk in front of Laura’s portrait. A key turns in the lock and in walks a woman. It’s Laura. “You’re alive!”

24. Punch-Drunk Love (2002)

Teetering on the brink of terminal depression, Paul Thomas Anderson’s beautiful pipe-dream of a modern romantic comedy turns the genre on its head with a mixture of skewed invention and giddy sincerity. Trust Anderson, one of the smartest talents in contemporary film, to find gainful employment for Adam Sandler, its most gormless clown; Sandler’s small-time entrepreneur Barry Egan is a vulnerable and touching creation, while Emily Watson, his expectant sweetheart, glows from within.

Best moment: Sandler races through the corridors of Watson’s apartment block, rings her doorbell, and they kiss as the music soars.

25. 50 First Dates (2004)

It’s another unexpected Sandler performance. He starts off true to type, playing Henry, an irritating frat-boy womaniser whom you wouldn’t trust any further than you’d throw him. But then he meets Lucy (Drew Barrymore), a sharp, sweet woman whose brain injury means she wakes up every day with no memory of what happened before her accident; he’s in love. Henry has to tell Lucy what happened, who he is, and that he loves her, every single day. The script has too many silly gross-out lines, but the scenario is just too emotional to put you off.

Drew Barrymore and Adam Sandler in 50 First Dates (2004) - Film Stills
Drew Barrymore and Adam Sandler in 50 First Dates (2004) - Film Stills

Best moment: Lucy learns that Henry has put the rest of his life on hold for her, and decides to send him away. “I have to make a new journal that doesn’t have you in it. But before I do… I really want you to read what I wrote about you.”

26. True Romance (1993)

It took Quentin Tarantino five years to find backing and a director (Tony Scott) for his first, most personal, script. An update of Badlands, Tarantino admits that it’s also the romantic fantasy of a single 25-year-old “movie geek”. Thus, Patricia Arquette’s endearingly ditzy trailer-trash blonde (Alabama) shares a love of kung-fu movies and Elvis with Clarence (Christian Slater). As their cocaine deal-of-a-lifetime goes wrong, the film bursts into a symphony of violence, and we root for this “real cute couple” to make it out alive.

Best moment: Alabama purrs: “I feel real goofy saying this, me being a call-girl and all, but I think I love you.”

27. Now, Voyager (1942)

Irving Rapper’s film gets stranger and more compelling as the years go by. Bette Davis plays a dowdy spinstress who’s transformed from an ugly duckling into a swan after a nervous breakdown. On an ocean cruise, she falls for the unhappily married Paul Henreid and ends up looking after his troubled daughter. As for marriage, she tells him: “Don’t let’s ask for the moon. We have the stars.” Romance doesn’t always have fairytale endings, then, but Davis’s transformation is gripping to behold.

Best moment: Henreid lights up two cigarettes, then hands one to Davis.

28. When Harry Met Sally (1989)

“We could never be friends,” announces Harry smugly. “Men and women can never be friends because the sex part always gets in the way.” Sally – a fresh, fluffy, all-American ditz – disagrees; 11 years and several regrettable hairdos later, they’re still arguing the point. Nora Ephron’s script, zinging with one-liners and verbal sparring, crystallises a perennial issue in the war between the sexes; Meg Ryan and Billy Crystal update Hepburn and Tracy in style.

Best moment: At the climactic New Year’s Eve party, Sally wails: “Harry, you say things that make it impossible for me to hate you, and I hate you, Harry, I really hate you!”

29. Titanic (1997)

James Cameron’s $200 million account of the world’s worst shipping disaster is also a classic tale of doomed love across the social divide. On an ocean liner bound for the States, a bored young English aristocrat (Rose, played by a ravishing Kate Winslet) discovers her soulmate in Jack, a penniless Irish charmer (Leonardo DiCaprio). But it’s not just the class system that’s against them – a 500,000-ton iceberg strikes a hole in the ship, and their passionate affair is sunk.

Best moment: “Promise me you’ll survive,” stammers the near-dead Jack as they float in the freezing North Atlantic. Rose clutches his hand: “I’ll never let go, Jack, I’ll never let go.

30. Lost in Translation (2003)

Sofia Coppola’s postmodern Brief Encounter is full of unspoken, low-key longing and tentative open spaces, proving that in romance, less is often more. It brings Bill Murray and Scarlett Johansson together by chance as guests in a Tokyo hotel; cut adrift from their normal lives and partners, they slowly and shyly come to recognise each other as kindred spirits. Darting through neon streets, holding hands, singing karaoke – nothing happens, but everything does.

Best moment: They’re falling asleep after talking all night; he tenderly holds her foot.

31. Brooklyn (2015)

With this pulse-quickening Irish immigrant tale, adapted from Colm Tóibín's 2009 novel, director John Crowley pulled off something special. Adrift in Fifties New York, young Eilis Lacey (Saoirse Ronan) meets sweet Italian-American Tony Fiorello (Emory Cohen), and the two are lost in each other’s eyes. But rural Ireland is a small, intense world that nobody truly escapes, and a tragic secret in Eilis’s family is about to call her home. With an utterly heartbreaking performance from Ronan at its centre, Brooklyn is an emotional masterpiece.

Best moment: Eilis finally finds the courage to open up to Tony: “The next time you tell me you love me – if there is a next time – I’ll… I’ll say I love you too​.”

32. Partie de Campagne (1936)

In Jean Renoir’s miniature masterpiece (only 39 minutes long), Henriette, a fresh and lovely Parisienne, takes a day trip to the country on a summer’s day with her maman, papa, and idiot husband-to-be Anatole. She’s utterly intoxicated by the gorgeousness of nature and, separated from her family, falls into the arms of young Henri, a handsome, poetic-looking sort. After a brief moment of passion in the long grass, the clouds burst; she heads back to humdrum domesticity with Anatole, but never forgets.

Best moment: As Henriette’s resistance to Henri crumbles, her eyes fill with tears when she hears a nightingale warbling in the tree above them.

33. I Know Where I’m Going (1945)

This black-and-white gem from Powell and Pressburger is as much an ode to the Western Isles as it is a tale of romance. Joan Webster (Wendy Hillier) is all set to marry a wealthy man, but bad weather prevents her from getting to the wedding. While she’s stranded, she meets Torquil MacNeil (Roger Livesey), a naval officer and the laird of Kiloran. She’s sucked into the otherworldliness of the Scottish islands, replete with superstitions, curses, ceilidhs and whirlpools.

Best moment: She’s leaving to marry her rich man. “Will you do something for me before I go away?” she asks. “I want you to kiss me.”

34. Breakfast at Tiffany’s (1961)

Purists maintain that the cinematic version of Truman Capote’s novel is a bowdlerised travesty; well, we still keep watching it. Director Blake Edwards transformed a slight, amoral tale into a poignant love story where two lost souls, Audrey Hepburn’s high-class call-girl Holly Golightly, and George Peppard’s failed writer, find each other in high-chic bohemian New York. Forty years later, every girl still wants to walk down Fifth Avenue in a Givenchy dress.

George Peppard and Audrey Hepburn on the set of Breakfast at Tiffany's (1961) - Corbis Historical
George Peppard and Audrey Hepburn on the set of Breakfast at Tiffany's (1961) - Corbis Historical

Best moment: That kiss at the end, in the rain, with Cat.

35. Bonnie and Clyde (1967)

The prototypical warped love story, and, for many, the first modern American movie, is a constant and effortless balance of tragedy and comedy, with a cloud of dread hanging over the proceedings. For us not to dismiss them as repugnant killers, the central duo needed to be very beautiful and genuinely touching – and we could have asked for no more than Warren Beatty and Faye Dunaway.

Best moment: Having just killed his first man, Clyde selflessly suggests to Bonnie that she leave him, adding: “You ain’t gonna have a minute’s peace!” Her trembling reply: “You promise?”

36. Annie Hall (1977)

Woody Allen’s funniest, saddest, finest film, about the life and one true love of Manhattan stand-up Alvy Singer, is almost unbearably heartbroken. It’s a lament for chances missed as well as a fond flashback to better times. Out of the great relationship of his life, Woody fashioned the great relationship of Alvy’s and the most personal, mature, reflective film of his career. He couldn’t have done it without Diane Keaton, whose Annie is unforgettable.

Best moment: The final montage of Alvy and Annie’s life together, set to Keaton’s achingly lovely rendition of “Seems Like Old Times”.