10 Best Period Rom-Coms, Ranked

Romantic comedies have become one of the most beloved genres throughout cinematic history. They are entertaining, they are funny, they are dramatic, and they produce some of the most swoonworthy and heartwarming moments that one could ever dream of. What could possibly make them any better? Well, perhaps if they were set back in time.

Indeed, history has often been romanticized for the silver screen, and so it only makes sense to interweave this setting into the narratives of a love story. Sometimes the past’s proclivity to propriety serves as a comedic juxtaposition to the goofiness of finding love. This may very well be the case for the freshly released film, Fly Me to the Moon, which appears to have stuck it’s landing. But, in the meantime, here are some other period rom-coms that will likely tickle your fancy.

10 ‘Much Ado About Nothing’ (1993)

Director: Sir Kenneth Branagh

As Hero (Kate Beckinsale) and Claudio (Robert Sean Leonard) await their upcoming marriage, they – along with Don Pedro (Denzel Washington) – unite to plot a match making scheme. Their targets are Benedick (Branagh), an arrogant self-proclaimed bachelor, and Beatrice (Dame Emma Thompson), his strong-willed verbal sparring partner. Little do the group know that a devious plan is being hatched by Don John (Keanu Reeves) who seeks to ruin the big wedding.

There’s an assumption that Shakespeare’s plays are often – if not always – serious. Perhaps its the occurance of melancholic family drama and the regularities of tragic deaths, however this assumed solemnity is far from the truth. Indeed, Much Ado About Nothing is one of the best classic comedies there is. In fact, the 1993 adaptation is particularly stellar, not only because of its A-List ensemble, but because of how they explore the love stories. Benedick and Beatrice are the underrated enemies-to-lovers couple. Their banter is unmatched as their biting words mask their underlying passionate affection. It really is such fun.

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9 ‘Hysteria’ (2011)

Director: Tanya Wexler

Set in London in the late 19th century, a struggling physician, Dr. Mortimer Granville (Hugh Dancy), is hired by Dr. Robert Dalrymple (Jonathan Pryce) to aid in providing treatments for women diagnosed with hysteria. But upon taking part in the manual medical procedures, an event transpires that leads to Granville inventing the first vibrator, all in the name of science.

Where Hysteria may not be the most historically accurate program, there’s no denying how it’s a very fun film. Indeed, despite its bold concept and the risk of being gratuitous, the movie radiates an immense amount of charm that stems from its silliness and outlandishness. The budding relationship between Granville and Charlotte (Maggie Gyllenhaal) is such a joy to watch as their back-and-forth banter makes their compatibility much more evident. The two are true twin flames as they exude the same passion and progessiveness, whether that be in regards to medicine or social justice.

8 ‘Emma’ (2020)

Director: Autumn de Wilde

Set in the 1800s Regency era, the wealthy and young Emma Woodhouse (Anya Taylor-Joy) amuses herself by meddling in the love lives of friends and family. Proud of her self-proclaimed match-making skills, Emma sets her eyes on Harriet Smith (Mia Goth) as her next project. But things go awry as Emma makes poor missteps that not only harm those around her, but also her own chance of finding love.

Vibrant and whimsical in its visuals and tone, this version of Emma radiates its own modern flare, despite its deeply classical setting. Indeed, with its interweaving of contemporary social themes, witty comedic gags, and occasional flashes of nudity – this Jane Austen adaption is truly fun and fresh. What’s even better is how they explore the relationship between Emma and Mr. Knightley (Johnny Flynn). Their friends-to-lovers journey is complex, yet tender as there’s an odd sweetness to them even if they appear awkward at times.

7 ‘The Importance of Being Earnest’ (1952)

Director: Anthony Asquith

Set in Victorian England, two friends, Jack Worthing (Michael Redgrave) and Algernon Moncrieff (Michael Denison), assume the identity of a fictional man named Ernest Worthing. But complications arise when they both establish romantic relationships under the false psudonym, leading the ladies they court to a time of utter confusion as the lies begin to catch up to the young men.

Where there’s been a more recent adaptation of this Oscar Wilde classic, the 1952 version harbours a nostalgic quality that cannot be matched. From its wit to its overtly theatrical performances, the film’s staginess is what brings out its charm. Indeed, despite it’s goofiness, audiences can’t help but root for the characters as they navigate the challenges of courtship within high society. Sure, it’s a bit wacky, but The Importance of Being Earnest is always a fun watch.

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6 ‘The Wedding Singer’ (1998)

Director: Frank Coraci

Robbie Hart (Adam Sandler) is a great wedding singer who knows how to keep the party going. Unfortunately for him, his own wedding doesn’t go that well as his fiancé unexpectedly leaves him at the alter. Robbie’s only consolation is his budding friendship with Julia (Drew Barrymore), a waitress who works at the same reception hall.

Despite not being a traditional period film, The Wedding Singer‘s setting of 1985 served as a distinctive narrative choice. Perhaps the warmth of 80s nostalgia was meant to enhance the wholesomeness of the main couple, because Sandler and Barrymore’s chemistry is one for the ages. They are lovable, they are charming, and they are oh so funny together. It’s no wonder why they’ve done two more rom-coms since this film’s release. Maybe they do just want to grow old with each other.

5 ‘My Fair Lady’ (1964)

Director: George Cukor

Snobbish phonetic professor, Henry Higgins (Rex Harrison), accepts a wager that he can transform an unrefined Cockney working-class girl, into a presentable lady of high society. The girl, Eliza Doolittle (Audrey Hepburn), agrees to take on speech lessons so as to improve her job prospects. And despite their frequent squables, the two form an unexpected bond.

Controversy struck when Hepburn was cast as Eliza instead of the character’s Broadway originator, the then relatively unknown Dame Julie Andrews. That said, despite all the drama, My Fair Lady has since become one of the most beloved golden age musicals of all time. It’s costumes remain striking to the eyes, as does the songs to one’s ears. And even though their relationship seems a little icky at first, the connection between Eliza and Higgins is clear. They may drive each other mad, but my golly do they work; a drastic change from the original ending of Pygmalion.

4 ‘Some Like it Hot’ (1959)

Director: Billy Wilder

In the winter of 1929, after witnessing a mob hit, two musicians – Joe (Tony Curtis) and Jerry (Jack Lemmon) – flee to escape the gangster who committed the crime. In doing so, they disguise themselves as women so that they can join an all-female jazz band. But complications set in as they get entangled in their own love plots. Joe starts to fall for the band’s singer, Sugar (Marilyn Monroe), whereas Jerry – whom as disguised as Daphne – catches the eye of a rich suitor who won’t take no for an answer.

Featuring one of her best, if not the best, performances of Monroe’s career, Some Like it Hot is laced with comedic charm and ever so lovely over-the-top performances. It’s energetic in every way and the chemistry between Curtis and Monroe is palpable from beginning to end. Some Like it Hot is a truly a comforting film that one can easily watch on a loop. Indeed, nobody may be perfect, but this film certainly almost is.

3 ‘Shakespeare in Love’ (1998)

Director: John Madden

Fictionalizing the life of famed playwright, William Shakespeare (Joseph Fiennes), this movie follows him at a time where he struggles with a severe case of writers-block. Desperately in search for his next muse, he ultimately finds it when he comes face to face with Viola De Lesseps (Gwyneth Paltrow), a noblewoman with a idealistic dream of becoming an actor.

Where some may see Shakespeare in Love as an odd fan-fic of the poet’s life, there’s no denying how it’s both entertaining and comforting. Indeed, from the compelling romance plot, driven masterfully by the leads’ electrifying chemistry, to the delightful humor laced throughout the narrative and the ensemble’s enthusiasm – what’s not to love? Sure, there may be tons of historical innacuracies, but this was never marketed as documentary. This was made for a good time.

2 ‘Pride & Prejudice’ (2005)

Director: Joe Wright

Set in England’s Georgian era, the five Bennet sisters are raised by the expectations of their mother who emphasizes life’s purpose of securing an advantageous marriage. Elizabeth (Keira Knightley) – the family’s strong-willed daughter – however, does not feel pressured to follow suit. But when a wealthy bachelor arrives in town, Elizabeth’s interests are reluctantly piqued; though not by Mr Bingley (Simon Woods), but his friend, Mr Darcy (Matthew Macfadyen) – a man she believes to be arrogant and loathesome.

Some may find it controversial to consider Pride & Prejudice as a rom-com. But let’s make it known that we’re not trying to reduce its literary value, but instead identify how this adaptation seems to share similar markers to some of the great rom-coms: there’s the classic meet-cute, the slow burn attraction, the sudden separation brought about by betrayal, then the final reconciliation. This doesn’t even cover the little humorous gags interweaved in many of the actors’ performances. Elizabeth and Darcy are the quintessential enemies-to-lovers couple. It would be wrong not acknowledge them.

1 ‘Rosaline’ (2022)

Director: Karen Maine

Before Romeo and Juliet, there were Romeo and Rosaline – though most people usually forget this. Indeed, as a retelling of Shakespeare’s most famous play,Rosaline follows her side of the story as she navigates life as Romeo’s jilted ex. Desperate to reclaim her love that was lost, Rosaline (Kaitlyn Dever) will do anything to separate the new couple.

With more creative adaptations being produced every year, Rosaline has become a truly underrated addition. Indeed, this anachronistic retelling is filled with fun as it jokes about how the best poets aren’t always the best romantics, and that the “perfect suitor” isn’t always one’s “true love”. Rosaline undergoes this journey of realisation; which is great, considering that she does so with the help of Dario (Sean Teale), an arranged suitor whom she strikes a love-hate relationship with. Aren’t we all suckers for a good annoyance-to-lovers trope?

Next: 10 Rom-Coms That Will Never Get Old, Ranked