The 25 best romantic comedies to watch this Valentine's Day

Gem Seddon
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The best romantic comedies are up there with the pinnacle of cinema's finest stories. Endearing, enchanting, and full of great dating advice (well, maybe that's debatable), these romantic movies are responsible for giving us some of Hollywood's favourite heartthrobs, greatest film quotes, and most iconic characters. Sure, they may be pretty corny, but isn't that part of what makes romance so, well, romantic?

What better way to spend Valentine's Day than snuggled up on the sofa with one of the best romantic comedies of all time? And, if you're stuck for choice, we're here to help with this list of cult classics to indie breakouts. Make sure you stock up on the tissues and chocolate beforehand – there will be tears.

Read more: Best romantic movie quotes | Best movies on Amazon Prime | Best movies on Netflix | Best movies on Disney Plus 

25. My Best Friend's Wedding (1997) 

The romance: Three weeks before her 28th birthday, food critic Julianne Potter (Julia Roberts) receives a phone call from her oldest friend Michael (Dermot Mulroney), telling her of his upcoming nuptials to the 20-year-old Kimmy (Cameron Diaz). Regardless, Jules is hell bent on keeping a pact the two made in college; if they aren't married by 28, they marry each other. Yeah, 28 is OLD in this movie.

Why it wooed us: This is as mainstream as rom-coms get. A starry cast, big-budget, and an amorous dilemma. Yet My Best Friend's Wedding approaches the setup from a fresher, less obvious angle. We don't always side with our heroine, and Kimmy, the woman we ought to despise? She's an absolute hoot! 

24. Roxanne (1987) 

The romance: The owner of a sizeable facial appendage, Charlie Bales (Steve Martin) tends to strike out with women: in particular, town newcomer Roxanne (Daryl Hannah). When she shows interest in one of Charlie's co-workers, the dim-witted Chris (Rick Rossovich), Charlie lends a hand, writing love letters on his behalf, confessing his love for her vicariously. 

Why it wooed us: Released at a time when Martin's output was at its peak, Roxanne treads the path between odd, tender and sweet. The overall message? Love comes in all shapes (ahem) and sizes (ahem... again). 

23. Enough Said (2013) 

The romance: After being introduced at a party, masseuse divorcee Eva (Julia Louis Dreyfus) begins dating Albert (James Gandolfini). Even in the early stages, their relationship holds promise. That is until Eva realises her latest client Marianne (Catherine Keener), an enigmatic poet journeying through her own divorce, is Albert's ex-wife. Unsurprisingly, it gets a bit awkward. 

Why it wooed us: Thank goodness, another smart, witty romantic comedy revolving around people over the age of forty. It works so well thanks to the chemistry between Dreyfus and Gandolfini.   

22. Love, Simon (2018) 

The romance: A coming-of-age high school movie about a gay teenager who enters into an online relationship with a mystery classmate, while trying to navigate the various perils of high school.

Why it wooed us:  Love, Simon is one of the most relatable high school movies in years, and it also just so happens to be groundbreaking in its depiction of a gay character in a mainstream teen flick. Director Greg Berlanti (best known for his TV work on The Flash) treats all of his characters with empathy, but Nick Robinson is a revelation as Simon. It’s a joy to watch the romantic mystery unfold, with unexpected surprises and second-guessed assumptions. Expect some tear-jerking moments along the way – this is a big-hearted hug of a movie that’ll leave you grinning ear-to-ear.

21. 10 Things I Hate About You (1999)

The romance: Cameron James (Joseph Gordon-Levitt) is head-over-heels for Bianca Stratford (Larisa Oleynik). Due to a stipulation by her father, Bianca can only date if her angsty sister Kat (Julia Stiles) does. So Cameron tries to convince the mysterious Patrick Verona (Heath Ledger) to date Kat. This is Shakespeare, so there are more entanglements, but you get the gist.

Why it wooed us: A modern take on The Bard's The Taming of the Shrew updated to a Seattle high school, the movie has a superb leading cast, all at the start of their careers. But its Allison Janney as the smut-scribing guidance counsellor who absolutely steals the movie. 

20. Trainwreck (2015) 

The romance: Having been taught from a young age that monogamy isn't realistic, magazine writer Amy (Amy Schumer) lives a life free from romantic commitment. That is until she finds herself falling for the subject of a new article she's writing, sports doctor Aaron (Bill Hader). 

Why it wooed us: Though it ends up being a lot more conventional than its set-up suggests, the winning central pairing of Schumer and Hader ensures that even classic tropes feel fresh. A consistently funny and genuinely affecting modern romcom that also delivers the most awkward cheerleader routine ever and a practically unrecognisable Tilda Swinton as Amy's barmy editor. 

19. The Princess Bride (1987) 

The romance: The beautiful Buttercup (Robin Wright) falls for farmhand Westley (Cary Elwes), who vows to seek his fortune before returning to marry her. When his ship is attacked by Dread Pirate Roberts (also Elwes) she believes he has perished and marries the insufferable Prince Humperdinck (Chris Sarandon). When a mysterious Man In Black comes to rescue her after Humperdinck has her kidnapped, he bears a striking resemblance to a young farm boy... 

Why it wooed us: Rob Reiner's fantasy rom-com mocks the typical swashbuckling fare which preceded it. It pushes William Goldman's screenplay to the hilt with super-quotable dialogue that still holds fast for fans. 

18. Chasing Amy (1997) 

The romance: Comic book creator Holden McNeil (Ben Affleck) meets fellow author Alyssa Jones (Joey Lauren Adams) and is immediately smitten. The pair hit it off – banter, laughs, the whole shebang. The twist in the tale? She's a lesbian.

Why it wooed us: Tackling a frankly tricky topic – the fluidity of sexual identity, contemporary masculinity – it still holds up as a funny as hell dive into modern romance. Points awarded for Holden's confession to Alyssa on their way home from dinner: moving, funny, and probably Kevin Smith's best monologue ever scripted. Well, Alyssa's response to Holden's prying, later on, comes pretty damn close to topping it actually. 

17. Moonstruck (1987) 

The romance: Sicilian New York widow Loretta (Cher) is set to marry Johnny Cammareri (Danny Aiello) – a man she likes but doesn't love – much to the enthusiasm of her parents. With Johnny back in Italy, he urges her to contact his younger, feisty brother Ronny (Nicolas Cage) to invite him to the wedding. They drive each other up the wall, which can only mean one thing, right? Cue fireworks.

Why it wooed us: The relationship between Loretta and her father Cosmo (Vincent Gardenia) is a treat. Their digs at each other are the foundation of the movie's chuckles. 

16. The Wedding Singer (1998) 

The romance: Jilted wedding singer Robbie Hart (Adam Sandler) befriends waitress Julia Sullivan (Drew Barrymore) during the run-up to her wedding to prized douche Glenn Gulia (Matthew Glave). With Robbie's help finalising the details for the big day, the two grow closer. Julia thinks she might be marrying the wrong man, a feeling Robbie soon shares as he uncovers Glenn's infidelity... 

Why it wooed us: This is Sandler at his absolute best: funny, compassionate and inherently likeable. Twinned with Barrymore's charming and goofy Julia, the pair's crazy chemistry harks back to Hollywood's golden era. 

Continue to Page 2 for more of the best rom-coms

15. Sixteen Candles (1984) 

The romance: Samantha's (Molly Ringwald) 16th birthday turns out to be less sweet than anticipated. The object of her affection, the hunky Jake Ryan (Michael Schoeffling), has gotten wind that she's nuts about him, the school geek (Anthony Michael Hall) is trying to get into her knickers, and no-one has remembered her birthday... 

Why it wooed us: John Hughes' teen romance is over 30 years old and still gives more recent high school flicks a run for their money. A good dose of one-liners, a charming central performance from Ringwald, and two guys vying for a woman's attention. It's the perfect rom-com formula. 

14. There's Something About Mary (1998)

The romance: Super-nerd Ted (Ben Stiller) tries to reconnect with his high school crush Mary (Cameron Diaz), years after an embarrassing incident with his zipper. When he hires slimy private detective, Healy (Matt Dillon) to track her down, it turns out there's more than one chap after her heart.  

Why it wooed us: The Farrellys balance gross-out humour (getting one's genitals trapped in a zip) with a bubbling romance at the centre of a romcom that's a rare breed of sweet and silly. 

13. The Lady Eve (1941)

The romance: Rich beer company heir Charles Pike (Henry Fonda) boards a cruise liner after a year down the Amazon. Before he's barely aboard, card shark Jean Harrington (Barbara Stanwyck) and her father peg him as an easy mark and set about scamming him of his riches. All's fair in love and war; Jean begins to regret their plan when her intentions for Charles switch from duplicitous to romantic... 

Why it wooed us: Fonda's a delight to watch as the unsuspecting buffoon falling for the wily charms of Stanwyck. Twice. Responsible for kickstarting the 'battle of the sexes' rom-com. 

12. Pretty Woman (1990) 

The romance: Classy hooker Vivian Ward (Julia Roberts) takes up with rich businessman Edward Lewis (Richard Gere) after taking advice from her quick-witted roommate Kit (Laura San Giacomo) that Lewis could become an established client. Hiring her to be his escort for the week, Edward and Vivian begin to foster feelings that go far beyond nookie.  

Why it wooed us: This was the performance that catapulted Roberts into the mainstream and into the public's hearts. And it's not hard to see why. 

11. Amelie (2001) 

The romance: Romantic dreamer Amelie (Audrey Tautou) discovers a box of hidden treasures in her apartment and vows to return them to their owner. It sparks a new zest for life, and a mission to help others realise their dreams. But what about Amelie's own happiness? There's a man about town she keeps bumping into... 

Why it wooed us: This bustling feel-good movie is more than a mere romantic comedy. You'll be smiling along with Amelie and holding out for the moment she takes her own advice. 

10. Four Weddings and a Funeral (1994) 

The romance: Hugh Grant's bumbling Brit Charles meets suave American Carrie (Andie Macdowell) at a series of social gatherings. They spend the night together, after which Carrie flies home to the U.S. to prepare for her own wedding to rich Scot Sir Hamish Banks (Corin Redgrave). Charles buries his feelings for Carrie and plans to marries his ex, Henrietta (Anna Chancellor). That is, until Carrie turns up at the church... 

Why it wooed us: A romcom classic, Four Weddings was the first time all the staple elements of British comedy melded together perfectly; a stellar cast, a cracking script and a slew of hilarious one-liners. 

9. High Fidelity (2000)

The romance: Record shop owner Rob (John Cusack) takes a trip down memory lane after his girlfriend Laura (Iben Hjejle) breaks up with him. While fighting off hideous visions of Laura having the best sex ever with new boyfriend Ian (Tim Robbins), Rob tracks down a series of exes to discover why exactly they ended things. Why? To win back Laura, of course. 

Why it wooed us: It reinvents a ton of rules that romcoms are often weakened by (breaking the fourth wall, two bickering, bantering side-kick employees Jack Black and Todd Louiso) and Cusack is never-better as anti-hero Rob. It's a cult classic for a reason, and it has a killer soundtrack. 

8. Bridget Jones's Diary (2001)

The romance: Perpetual singleton Bridget (Renee Zellweger) is desperate to find the perfect man. Fate throws two potential suitors her way in the form of lecherous schmooze Daniel Cleaver (Hugh Grant) and stuffy dullard Mark Darcy (Colin Firth).

Why it wooed us: The big-screen adaptation of Helen Fielding's pioneering chick-lit accomplished what many comedies geared at women fail to do – make us laugh. Zellweger is perfectly cast, dropping all traces of her Texan drawl, bringing to life the hilariously flawed Bridget.

7. His Girl Friday (1940)

The romance: Boorish-yet-somehow-utterly-charming editor Walter Burns (Cary Grant) chucks a spanner in the works of his ex-wife Hildy Johnson's (Rosalind Russell) imminent second marriage to Bruce Baldwin (Ralph Bellamy). Tempting the former newshound reporter with a murder story, she's helpless to say no, especially when there's a promising scoop at stake.

Why it wooed us: Grant's banter with Russell at the table, while endlessly quizzing her new fiance, is hysterical. His fast-paced rap-dialogue and Russell's slapstick make this an affair to remember.

6. The Philadelphia Story (1940)

The romance: Wealthy Philadelphia It girl, Tracy Samantha Lord Haven (Katharine Hepburn) finds herself at the centre of a four-way romantic tangle on the eve of her second set of nuptials. With the arrival of her first husband, the witty C.K. Dexter Haven (Cary Grant) comes fast-talkin' reporter Macauley (James Stewart) to cover the events of her wedding to reliable George Kittredge (John Howard). 

Why it wooed us: Grant and Stewart fighting for a woman's affections, using two completely different approaches, remains absolutely classic. 

Continue to Page 3 for more of the best rom-coms

5. Sleepless in Seattle (1993)

The romance: Widower Sam Baldwin (Tom Hanks) opens his heart after his wife's death live on radio, at the urging of his son Jonah. When Annie (Meg Ryan) hears his story, she re-evaluates her engagement and scribbles a letter to Sam asking him to meet her at the top of the Empire State Building... 

Why it wooed us: Nora Ephron's tale is now almost 30 years old, and had all the hallmarks of being a classic even then. It's funny and warm without drowning in schmaltz. Hanks and Ryan's palpable chemistry is a remarkable feat considering they barely share any screentime. 

4. Some Like it Hot (1959)

The romance: Jazz musicians Joe (Tony Curtis) and Jerry (Jack Lemmon) end up on the run after witnessing the St. Valentines Day massacre. Masquerading as buxom women, they hide out as members of touring all-female music troupe, Sweet Sue's Society Syncopators – where they meet Sugar Kane (Marilyn Monroe), a breathy singer who they each attempt to woo. In disguise... 

Why it wooed us: Billy Wilder pulled out all the stops at a time when censors frowned upon any kind of sexual tomfoolery. Shocking the MPAA with his tale of two transvestites after a bit of hot totty while escaping the clutches of the law, there's no finer environment for Curtis and Lemmons' comedic skills. 

3. Annie Hall (1977) 

The romance: Neurotic comedian Alvy Singer (Woody Allen) explores the doomed nature of his past romantic relationships, in particular his most recent paramour, Annie (Diane Keaton). The two meet through friends, and embark on what Alvy considers to be an unusual relationship. She's a free-spirited hipster while he remains the introspective analyst. 

Why it wooed us: The subtitled scene following the pairs initial meeting, on a Manhattan rooftop, is pure cinema gold: a sterling example of Allen's quick wit. While Annie and Alvy are conducting a seemingly trivial conversation concerning a date, subtitles flash up to reveal what's actually being conveyed. 

2. It Happened One Night (1934)

The romance: Snobby socialite Ellen Andrews (Claudette Colbert) goes on the lam, relinquishing her rights as heir to the family fortune to elope with her new spouse. On the way, she meets and falls for the charms of a no-nonsense journalist Peter Warne (Clark Gable) during a cross-country trip. 

Why it wooed us: The original rom-com, Frank Capra's flick is a landmark 'screwball' comedy. It introduced the now-popular formula of a mismatched couple who eventually fall in love. 

1. When Harry Met Sally (1989) 

The romance: Wise-crackin' Harry (Billy Crystal) and the progressive Sally (Meg Ryan) strike up a fiery friendship during a rideshare home from university, which ignites a series of chance meetings. Across a little more than a decade, the two challenge each other, bicker, disagree, yet continue to be drawn together.  

Why it wooed us: Based on the real-life tribulations of director Rob Reiner following his divorce, it was and still is a refreshing romantic comedy. The combo of Crystal and Ryan revived a gasping genre, exploiting the differences between the sexes to killer effect with heaps of guffaws that never seem contrived. And of course, there's Ryan's scene in the deli, making men (and women) the world over stand up and take notice.