Without immediately defaulting to cliche, the holidays and romantic comedies are an undeniably perfect match. Some of the very best Christmas movies are rom-coms, in fact. Both liberally trade on nostalgia, throw in relationship tension (and often difficult wider family dynamics), and are, at their best, unrivaled sources of escapism and comfort.
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They don’t tend to be made with anything like the same frequency these days, with a sneering cynicism directed towards the sub-genre that tends to bundle everything in with the Hallmark Movie stamp. But that’s unfair to both parties.
Romantic comedies look better against a back drop of snow and twinkling lights, and it’s impossible not to be completely suckered in when the stories are great. And if you can root for the leads through their carefully constructed dramas, the pay-off is always a little more magical when the holidays are involved. Here’s the best of the genre to rewatch this or any Christmas.
10 10. Bridget Jones’s Diary (2001)
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Bridget Jones’s Diary PG-13
Based on the novel by Helen Fielding, the rom-com Bridget Jones’s Diary revolves around a 32-year-old single woman who keeps a diary of her life and romantic encounters. Starring Renée Zellweger, Colin Firth, and Hugh Grant, the 2001 movie was a massive commercial and critical success.
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*Availability in US Release Date April 13, 2001 Runtime 97 Minutes Cast Renée Zellweger , Gemma Jones , Celia Imrie , James Faulkner , Jim Broadbent , Colin Firth Director Sharon Maguire
Despite more recent issues with how the character is presented in her earliest movies, Bridget Jones is basically the poster child for romantic slapstick, and the original throws in a Christmas hook that makes it an almost irresistible annual rewatch.
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The film takes in ugly Christmas sweaters, the eternal pain of family gatherings, and an age-old love triangle between Renee Zelwegger’s lead, Colin Farrell’s bumbling Mark Darcy, and Hugh Grant’s delightfully caddish Daniel Cleaver. There’s heart, humour, and a hot chocolate-like affirmative ending that makes all the awkwardness worthwhile.
9 9. While You Were Sleeping (1995)
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8/10 While You Were Sleeping PG
While You Were Sleeping is a romantic comedy-drama that stars Sandra Bullock as Lucy, a lonely Chicago Transit Authority worker who falls for a commuter, played by Peter Gallagher. After saving him from an oncoming train, she is mistaken for his fiancée while he is in a coma. The film explores themes of mistaken identity, family dynamics, and unexpected love. Bill Pullman co-stars as the man’s brother.
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*Availability in US Release Date April 21, 1995 Runtime 103 minutes Cast Sandra Bullock , Bill Pullman , Peter Gallagher , Peter Boyle , Jack Warden , Glynis Johns Director Jon Turteltaub
Lesser-known than some of the others here, While You Were Sleeping is your typical case of a near-death experience leading to romantic identity theft. What better foundation for a wholesome love story?
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Sandra Bullock’s Lucy is cut from similar cloth to Bridget Jones, lonely, unlucky in love and hopelessly lost in a love triangle of her own making. Set mostly around Christmas as an excuse to bring the family she fakes her way into together, the movie does actually have a positive message in there. It’s just delightfully wrapped up in the kind of festive cynicism that leads to the best rom com drama.
8 8. Serendipity (2001)
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Serendipity PG-13
Serendipity is a romantic comedy that follows the chance meeting of two strangers who leave their future together up to fate. Years later, they are each engaged to others yet find themselves compelled to seek out one another, relying on signs and serendipitous moments to guide their paths. The film explores themes of destiny, love, and the impact of seemingly random encounters on life’s journey.
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*Availability in US Release Date October 5, 2001 Runtime 90 Minutes Cast John Cusack , Kate Beckinsale , Jeremy Piven , Bridget Moynahan , John Corbett , Molly Shannon , Eugene Levy , Lilli Lavine , Michael Guarino , jr. , Abdul Alshawish , Stephen Bruce , David Sparrow , Gary Gerbrandt , Ann Talman , Crystal Bock , Kate Blumberg , Ron Payne , Marcia Bennett , Eve Crawford , Victor A. Young Director Peter Chelsom Expand
Again, Serendipity has a bit of a nasty streak on paper, because it weighs up the cost of infidelity against the irresistible draw of destiny. If you’re of the romantic persuasion that forgives all in the name of fate, it’s one you can’t not watch. Fundamentally, the plot boils down to the old adage that what’s meant for you won’t pass you by.
Despite the conceit sort of relying on home-wrecking, Serendipity is surprisingly warm and very charming, with John Cusack on fine everyman form as Jonathan, who meets his soul mate in Kate Beckinsale’s Sara while Christmas shopping at Bloomingdales. Their love story is very sweet, and the film has only grown better with time.
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7 7. Just Friends (2005)
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Just Friends PG-13
Just Friends is a romantic comedy directed by Roger Kumble, featuring Ryan Reynolds as Chris Brander, a formerly overweight high school nerd turned trendy music executive. Returning to his hometown for the holidays, Chris tries to reconnect with his high school crush but finds himself reverting back to his old, awkward self.
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*Availability in US Release Date November 23, 2005 Runtime 96 minutes Cast Ryan Reynolds , Amy Smart , Anna Faris , Chris Klein , Christopher Marquette Director Roger Kumble
Before Deadpool megastardom, Ryan Reynolds brought his brand of easy Canadian charm to this chaotic, and still very funny Christmas comedy about the living hell that is the friend zone. Probably not one that would fly by today’s standards, of course, but it’s a good set-up for a series of unfortunate events that lead him to reconnect with his childhood crush and best friend, Jamie (Amy Smart).
Just Friends‘ Christmas set-up brings Reynolds – a record label executive who used to be a loser – back to his small town home with Anna Faris’ hilarious popstar, who – along with a very good turn by Chris Klein – stands in the way of true love. Faris steals basically every scene, but Reynolds’ version of All-4-One’s “I Swear” is almost worth the rewatch alone.
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6 6. The Family Stone (2005)
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9.8/10 The Family Stone PG-13
The Family Stone is a comedy-drama film directed by Thomas Bezucha. Released in 2005, it stars Sarah Jessica Parker, Diane Keaton, and Dermot Mulroney. The story revolves around the Stone family’s Christmas gathering, where tensions arise due to the arrival of an uptight woman who is introduced as the eldest son’s girlfriend. The film explores themes of family dynamics, acceptance, and the challenges of blending different personalities.
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*Availability in US Release Date December 16, 2005 Runtime 104 Minutes Cast Claire Danes , Diane Keaton , Rachel McAdams , Dermot Mulroney , Craig T. Nelson , Sarah Jessica Parker , Luke Wilson , Brian White Director Thomas Bezucha
It’s a travesty that this ensemble comedy — featuring talent as starry as Diane Keaton, Luke Wilson, Rachel McAdams, and Sarah Jessica Parker – isn’t more fondly remembered. Critics weren’t bowled over nearly 20 years ago, but The Family Stone really understands the difficulty of family dynamics during the holidays.
There’s the right touch of screwball high-jinx, but there’s also a commitment to more important festive messages like love, acceptance, and the horror of having to integrate with your loved one’s family when you’re nothing like them. And there’s just enough of a tragic note behind all the chaos to genuinely dial up some real emotion.
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5 5. The Holiday (2006)
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8.3/10 The Holiday pg-13
The Holiday is a 2006 rom-com starring Cameron Diaz, Kate Winslet, Jude Law, and Jack Black. Directed and written by Nancy Meyers, The Holiday tells the story of two women who arrange a home swap to take a break from the stress of their recent breakups. But things take a turn when they both fall in love with local men.
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*Availability in US Release Date December 14, 2006 Runtime 138 Minutes Cast Cameron Diaz , Jude Law , Jack Black , Kate Winslet Director Nancy Meyers
The Holiday’s plot is almost inconsequential now: but all you really need to remember is that a house swap between two women (Cameron Diaz and Kate Winslet) seeking an escape from heartbreak leads to both of them accidentally falling in love with inconvenient new love interests (Jude Law and Jack Black).
The film wears its aspirations to be a golden age romance on its sleeves, even using the presence of Eli Wallach’s retired Hollywood screenwriter as a chance to deconstruct some of the genre’s more famous tropes. It’s now almost known as much for Jude Law’s outrageous camera flirting as anything else, but it’s the kind of Christmas film that immediately captures the warmth needed.
4 4. You’ve Got Mail (1998)
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8.5/10 You’ve Got Mail PG
Directed by Nora Ephron, You’ve Got Mail follows Joe and Kathleen, two strangers who meet in an AOL chatroom and begin a relationship over email, unaware that they are actually a lot more connected to one another than they think. Tom Hanks and Meg Ryan star as Joe and Kathleen, with a further cast that includes Parker Posey, Jean Stapleton, Dave Chappelle, and Greg Kinnear.
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*Availability in US Release Date December 18, 1998 Runtime 119 minutes Cast Dave Chappelle , Tom Hanks , Greg Kinnear , Jean Stapleton , Parker Posey , Meg Ryan Director Nora Ephron
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There’s a rich thread of nastiness in some of the best rom-coms, and You’ve Got Mail is decidedly cynical, despite its belief in the enduring power of love. Some might say it’s not strictly a Christmas film, but they’d be wrong: it’s a holiday movie because all of the key points of the movie happen at the Most Wonderful Time Of The Year for good reason.
Meg Ryan’s bookstore owner falls head over heels with her internet pen pal (Hanks), while hating the real life version of him, in a very overt nod to Pride & Prejudice. With added dial-up. The film is all about their chemistry as their frost thaws over a period of months. Is it better than Sleepless In Seattle? It’s debatable, but there’s just a little more magic to this one because we get to see Ryan and Hanks on screen together more.
3 3. Scrooged (1988)
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Scrooged PG-13
Scrooged is a Christmas comedy film by director Richard Donner, released in 1988. In this modernized take on Charles Dicken’s A Christmas Carol, Bill Murray stars as a narcissistic and selfish television executive named Frank Cross, who looks to put on a big-budget Christmas show for his network while trampling anyone in his way. However, his plans are interrupted when three ghosts of Christmas visit him to coax him to change his ways.
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*Availability in US Release Date November 23, 1988 Runtime 100 Minutes Cast Bill Murray , Carol Kane , Karen Allen , Alfre Woodard , Bobcat Goldthwait , Robert Mitchum , Michael J. Pollard , John Forsythe , John Glover , David Johansen Director Richard Donner
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Yes, it is a rom-com. Scrooged’s modern retelling of A Christmas Carol brings the best out of Bill Murray, who balances his signature deadpan humor with the very real feeling that he’s moments away from a full manic episode. He plays a cynical TV executive, determined to wring all he can out of Christmas, who is forced to reevaluate his life when Dickens’ famous ghosts come knocking.
Murray is deliriously good as Frank Cross, and the rom com element comes in when he realizes not just that he poisoned his own soul through greed, but that the route of it all was his lost love, Claire (Karen Allen). It’s all surprisingly emotional, as well as very funny, and Carol Kane’s take on the Ghost of Christmas Present is a joy worth watching every year.
2 2. Love Actually (2003)
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8/10 6.7/10 Love Actually R
The 2003 romantic comedy Love Actually follows various couples as they explore their relationships throughout the Christmas season. With a star-studded cast composed of Bill Nighy, Colin Firth, Alan Rickman, Emma Thompson, Keira Knightley, Hugh Grant, Laura Linney, Liam Neeson, Rowan Atkinson, Chiwetel Ejiofor, Martin Freeman, and Martine McCutcheon, Love Actually has since become a Christmas staple for rom-com lovers.
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*Availability in US Release Date November 14, 2003 Runtime 135 minutes Cast Colin Firth , Emma Thompson , Liam Neeson , Keira Knightley , Chiwetel Ejiofor , Laura Linney , Alan Rickman , Hugh Grant , Bill Nighy , Andrew Lincoln Director Richard Curtis
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Another ensemble rom-com, Love Actually has become a holiday classic to such a degree that people line up every year with the same steaming hot take about how everyone involved is horrible. But that’s sort of the point: Love Actually is about the total agony of falling in love – it’s messy, painful, inconvenient, and often just plain nasty.
Interweaving multiple love stories, that each seek to show different facets of romance over Christmas, it’s a brutally perfect exercise in emotional exploitation that loses nothing for that intent. The characters are more like caricatures, but the talent on show makes even the worst of them entirely charming, and it’s a staple around the world for good reason.
1 1. When Harry Met Sally (1989)
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10/10 9/10 When Harry Met Sally R
Written by Nora Ephron and directed by Rob Reiner, When Harry Met Sally chronicles the life and relationship of Harry Burns and Sally Allbright, who meet just after college on a road trip to New York City and begin a decade-long relationship that slowly evolves from friendship to true love. Billy Crystal and Meg Ryan star as Harry and Sally, with a further cast that includes Carrie Fisher and Bruno Kirby.
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*Availability in US Release Date July 21, 1989 Runtime 95 minutes Cast Bruno Kirby , Meg Ryan , Carrie Fisher , Steven Ford , Billy Crystal Director Rob Reiner
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Again with the mean spirit of Christmas. When Harry Met Sally’s qualification as a holiday movie comes thanks to its climactic scene set over New Year’s Eve, and some other Christmas elements that make the relationship unavoidable. More importantly, it captures exactly the feel of festive romance.
The film’s exploration of love and bad timing still feels like the blueprint to so many sitcom romances that followed, meaning it has an eternal relevance even now. Billy Crystal and Meg Ryan’s chemistry as the titular leads is tangible from the moment of their meet-cute, and you really get the sense that their final fate is earned by the time it comes. And for all that meanness, there’s a beautiful heart beating behind the story.
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