The 30 greatest romcoms ever, ranked in order of guilty pleasure romantic bliss

14 February 2023, 10:24 | Updated: 4 December 2023, 17:31

Picture: Warner Bros/Rank Film/United International

By Tom Eames and Sofia Rizzi

It's the week of Valentine's Day, and that can only mean one thing: picking a classic romcom to watch!

Having said that, we can't help but watch a romantic comedy movie (or two) all year round. In fact, the cheesier the better.

We've painstakingly picked our 30 absolute favourite romcoms of all time. Are yours in there?

  1. The Wedding Planner

    Jennifer Lopez plays Mary Fiore, a highly-esteemed wedding planner. She has plans and rules for everything, but drama ensues when she breaks one of her own rules – she falls in love with the groom.

    We don’t blame her, he just happens to be a dashingly handsome doctor (Matthew McConaughey). This is on the cheesier end of the rom-com spectrum, but that noughties charm makes the film even better almost twenty years down the line.

  2. Sweet Home Alabama

    If you name your film after a classic rock banger, you're always in for a winner.

    Reese Witherspoon stars as a snooty fashion designer who returns to her roots and to finally get a divorce from her estranged husband, Jake.

    However, it's not long before she realises what makes her happiest: home and her hubby.

  3. What Women Want

    An underrated gem, What Women Want stars Mel Gibson and Helen Hunt.

    He plays Nick Marshall, a chauvinistic executive who by some freak accident gains the power to hear women’s thoughts, as you do.

    What he first finds more of a burden than a gift actually turns Nick into a nicer guy, and he just about manages to get the girl by means of his powers.

  4. Crazy Stupid Love

    Ryan Gosling. Steve Carrell. Emma Stone. Need we say more?

    Steve Carell plays Cal, a middle-aged divorcee who finds himself lost after his marriage falls through. Handsome and successful Jacob (Ryan Gosling) takes Cal under his wing and tries to teach him a thing or two about love (or lack thereof).

    While Jacob is teaching Cal the tricks of the single man’s trade he happens to fall for a girl. Things go wrong and truths are outed – we’ll leave the rest for you to find out.

  5. Definitely, Maybe

    Essentially, this film stole the plot of How I Met Your Mother, but we still love it.

    Ryan Reynolds plays a political consultant who tries to help his 11-year-old daughter understand his divorce by telling her the story of his past romantic relationships and how he ended up marrying her mother.

    We won't spoil the ending, but it'll keep you guessing from the start.

  6. Serendipity

    Cheesy but great. Jonathan (John Cusack) and Sara (Kate Beckinsale) meet by chance, and are into each other, but Sara feels like she has to make sure it’s destiny.

    “There are no accidents” – so, she writes her name and number in a book and gives it to a random bookshop. If Jonathan finds the book, it’s meant to be.

    We'll just gloss over the fact they're both engaged to other people.

  7. Music and Lyrics

    Sure, this film is as cheesy as it gets, but any film with Hugh Grant as an Andrew Ridgeley-type in a Wham-style '80s duo is already fantastic.

    Drew Barrymore also stars as a songwriter who helps Hugh make a pop comeback, and it's rather heartwarming.

  8. Last Christmas

    Last Christmas Trailer # 2

    One of the best romcoms in recent years, and it has added George Michael and Wham! music, what more could you want?

    Emilia Clarke and Henry Golding star in this Christmas-themed romance set in London, but you can watch it any time of year.

  9. 50 First Dates

    This is a really original idea for a rom-com - it’s pretty sad but also surprisingly funny.

    Set in Hawaii, Henry (Adam Sandler) is well-versed in the art of being a single bachelor until he meets Lucy (Drew Barrymore). The pair hit it off, but what rom-com would be complete without a little complication?

    So what’s the twist here? It just so happens that Lucy has short-term memory loss and forgets who Henry is every day when she wakes up. How does he solve the problem? Watch the film and find out...

  10. Overboard

    Technically, this film has a dodgy message. What with kidnapping a woman with severe amnesia and pretending she's your wife. But it's fine in the end. We think.

    Real-life couple Goldie Hawn and Kurt Russell star in this brilliant romcom, where snooty heiress Joanna treats handyman Dean with zero respect, before he rescues her from going overboard her ship. Hence the title, see?

    After finding out the truth, she realises that she actually prefers her new life, and that her old family and partner were somehow even worse. Ah, the '80s.

  11. My Big Fat Greek Wedding

    Most rom-coms are heavy on the romance and take it easy on the comedy, but My Big Fat Greek Wedding will have you in stitches from the word go.

    The plot is one of the most heartwarming stories of family and love that you’ll find in a rom-com.

    It follows Toula (Nia Vardalos) who works in the family restaurant on her journey of finding her identity and coming to terms with her heritage, where to her family’s horror she falls in love with a man who isn’t Greek (heaven forbid). There’s lots of lamb, plate throwing and overt hand gestures. You’ll love it.

  12. Hitch

    Have you seen that Channel 4 dating show Flirty Dancing? Ashley Banjo is essentially Will Smith from this movie.

    'Date doctor' Hitch helps awkward guys succeed at dates (in a non-sleazy way, promise), while also trying to find love with Eva Mendes's Sara. This was Will Smith at his slick best.

  13. Just Like Heaven

    A slightly sci-fi twist on the romcom genre, as Reese Witherspoon plays a doctor in a coma, whose spirit 'haunts' the apartment now owned by Mark Ruffalo.

    They obviously end up falling in love, despite the obvious issues, but will she ever wake up? A true guilty pleasure.

  14. Maid in Manhattan

    Throw realism out of the window, throw in a Senatorial candidate (Ralph Fiennes) and a maid down on her luck (Jennifer Lopez) and you have the great chick-flick Maid in Manhattan.

    Thanks to her son Ty and some fancy borrowed clothes, the senator and Marisa (JLo) fall in love, before he finds out she’s actually a maid in disguise.

    Although you totally know where this film is going, there’s still a lot of satisfaction in watching Marisa get swept off her feet by the handsome Senator.

  15. Return to Me

    On paper, this sounds ridiculous. But it's actually one of the most underrated and heartwarming romcoms ever.

    David Duchovny's wife dies in a car accident, only for her heart to be donated to Minnie Driver, who he by chance meets and falls in love with. Again, sounds awful, but it's beautiful.

  16. About Time

    This film has two love stories running through it, and we must admit it’s truly heart breaking at times.

    Tim (Domhnall Gleeson) discovers a family secret when he turns 21 that changes his life forever – you’ll have to watch to find out what it is.

    His main ambition in life is to get a girlfriend, though it doesn’t go incredibly smoothly. Meanwhile, there is a sad twist in the tale which involves Tim’s father (Bill Nighy). It’s safe to say we weep every time.

  17. My Best Friend's Wedding

    There’s one thing that sets this film apart from other rom-coms, it doesn’t end the way you think it will.

    As the title suggests, the story is about Julianne’s (Julia Roberts) best friend Michael (Dermot Mulroney, swoon) who gets married.

    She realises that she’s actually in love with him, and she sets out to try and tell him before it’s too late. We won’t spoil the ending for you, but it’s definitely worth a watch!

  18. 500 Days of Summer

    If you’re looking for a quirkier take on the boy-meets-girl classic, then look no further than 500 Days of Summer.

    It’s an offbeat rom-com about Summer (Zooey Deschanel) who doesn’t believe in true love and Tom (Joseph Gordon-Levitt) who falls in love with her: “This is not a love story, it’s a story about love”.

    The film is also visually beautiful and quirky, and the soundtrack is a welcome change to your standard rom-com pop hits.

  19. The Wedding Singer

    Before 50 First Dates, Adam Sandler and Drew Barrymore were already adorable, and it was all set back in the '80s.

    Not only does it have a fantastic nostalgic soundtrack, but it's sweet, hilarious and naughty all at once.

  20. Some Like it Hot

    One of the first romcoms decades before it was a 'thing', Marilyn Monroe stars in this timeless comedy.

    Jack Lemmon and Tony Curtis co-star as cross-dressing musicians on the run from the mob, and it'll never not be funny.

  21. Groundhog Day

    Bill Murray proved he can be a leading man in a romcom in this fantastical classic, in which he experiences the same darn day over and over.

    He eventually learns the error of his ways, becomes a better person, and falls in love with Andie McDowell in the process. He must surely be sick of 'I Got You Babe', though.

  22. While You Were Sleeping

    Another slightly dodgy concept, in which Sandra Bullock accidentally pretends that Sandy off The OC is her fiancé after he falls into a coma.

    Instead, she soon falls in love with his brother, played by Bill Pullman. And they get engaged without even kissing. Only at the movies!

  23. Love Actually

    To not only be on the best rom-coms chart of all time, but also the Christmas favourites list means that Love Actually really is a one-off.

    We won’t explain the plot as you’ve either seen it at least ten times, or you’ve never seen it, in which case we won’t spoil a single second for you.

    There’s everything you need for the perfect film: a great cast, storylines that tug at the heart strings, a wealth of eye candy, bad Christmas music and of course, an epic airport chase. This is a work of genius by Richard Curtis – we thank and salute you.

  24. Four Weddings and a Funeral

    This was arguably the film that made British romcoms as popular as its American counterparts, and catapulted Hugh Grant into the hearts of everyone.

    Read more: Four Weddings and a Funeral cast then and now

    Charles and his friends are in wedding season, while he keeps bumping into a spoken-for American (Andie McDowell is back). Peak '90s, and we love it for it.

    "I feel it in my fingers..."

  25. Sleepless in Seattle

    Tom Hanks and Meg Ryan's first movie together was one of the first true romcoms as we know it today.

    This one's particularly strange, in that they don't even meet until the very end. But the journey for them to get there is always worth a watch.

  26. Bridget Jones's Diary

    Bridget Jones (Renée Zellweger) finds herself in her 30s, going for the wrong men and choosing vodka and Chaka Khan over taking control of her life. But all that changes when dashing Mark Darcy (Colin Firth) comes on to the scene.

    There’s a lot of misunderstanding, a typically British lack of communication, a cheeky Hugh Grant, and a bucket of one-liners that will have you rolling about laughing. It’s an absolute classic, and it also has a really great soundtrack.

  27. Pretty Woman

    Pretty Woman was released in the golden era of rom-coms, the early '90s, and has stood the test of time.

    Richard Gere and Julia Roberts play businessman Edward and escort Vivian who end up falling for each other (you wouldn't think it was a Disney film, technically!).

    Though they come from two completely different worlds, Edward pays to spend the week with Vivian and the pair fall in love.

    There’s also a shopping montage to Roy Orbison's ‘Pretty Woman’, winner.

  28. Notting Hill

    Ok, so maybe this isn’t the most realistic of rom-coms, but we love it nevertheless.

    The life of a humble bookshop owner William Thacker (Hugh Grant) is turned upside down when the world’s most famous film star (Julia Roberts) walks into his shop.

    The plot thickens with the addition of an absurd flat mate, a burnt guineafowl, and mayonnaise masquerading as yoghurt. William just happens to pull of that impossible combination of awkward and charming, as only Hugh Grant could.

  29. When Harry Met Sally

    Nora Ephron brings us one of the world’s most-loved rom-coms. If you haven’t seen this iconic film then put everything on hold, ignore the to-do list for today and watch it tonight.

    It’s a will-they-won’t-they film following best friends Harry and Sally, played by Billy Crystal and Meg Ryan, navigating their love lives from their meeting at University to their adult lives.

    When Harry Met Sally is classic on so many levels – that vocal café scene with Meg Ryan, Billy Crystal’s pronunciation of ‘pecan pie’, and of course, Meg Ryan’s permed hair. Watch it.

  30. You've Got Mail

    Where do we begin with You’ve Got Mail? Charming pretty much sums it up in one word.

    Meg Ryan plays Kathleen Kelly, a bookshop owner in Manhattan, who meets book mega-store mogul Joe Fox (Tom Hanks). The pair are at business war, but simultaneously fall in love over the internet.

    This came way before the days of questionable catfishing, and we can vouch for it, it’s actually a great plot. The combination of Tom Hanks and Meg Ryan is a total winner in this film too. It’s another rom-com gift Nora Ephron has given the world.