Courtesy Everett Collection; Simon Mein; Michael Gibson

11 holiday rom-coms, ranked

Updated

‘Tis the Season for Romantic Comedies

You can keep your Christmas Carols and your Wonderful Lifes — when the holidays roll around, nothing is as satisfying as a good old-fashioned rom-com. Nancy Meyers’ The Holiday celebrated its 10th anniversary in 2016, and in honor of a decade of Cameron Diaz and Kate Winslet’s transatlantic holiday home-swap, we’ve ranked 11 entries to the genre that bring holiday cheer as much as romantic wish fulfillment. Check out our countdown ahead.
11. New Year’s Eve (2011)

The late Garry Marshall contributed many wonderful things to the world of film and television; his trio of ensemble rom-coms each centered on a different holiday is not one of them. The second of these was 2011’s New Year’s Eve, a mind-numbingly shallow effort that followed the Dec. 31 adventures of dull characters played by Sarah Jessica Parker, Halle Berry, Jessica Biel, Robert De Niro, Zac Efron, Lea Michele, Ashton Kutcher, Katherine Heigl, Josh Duhamel, and Jon Bon Jovi, among a host of other big stars — huge — all of whom deserve better.

 

 

10. Just Friends (2005)

Roger Kumble’s rom-com stars Ryan Reynolds as Chris, a music industry hotshot and former fat kid who accidentally winds up back at home at Christmastime with one of his clients, a moronic pop star (Anna Faris). He takes advantage of his unexpected homecoming by trying to break out of the friend zone with his childhood best friend (Amy Smart). Relying primarily on fat jokes for its humor and Chris’ sense of entitlement for its love story, Just Friends is as un-romantic and un-comedic as a rom-coms can be.

9. Four Christmases (2008)

Reese Witherspoon and Vince Vaughn play a stubbornly unmarried couple that takes an exotic vacation every Christmas in order to avoid spending time with family in Seth Gordon’s comedy. One year, their families find out that their flight has been canceled, so they are forced to visit each of their four divorced parents on Christmas Day — which, in turn, forces them to reveal to each other who they really are and confront some hard truths about their relationship. Technically it’s a holiday romantic comedy, but somehow this cynical flick is utterly devoid of the cheer that typically comes with the season or the genre.

8. The Family Stone (2005)

When Everett (Dermot Mulroney) brings his uptight girlfriend (Sarah Jessica Parker) to his liberal family’s house for Christmas (you know they’re wacky and bohemian because everyone calls the parents by their first names), poorly sketched family dysfunction and contrived misunderstandings ensue. Diane Keaton and Craig T. Nelson are great as Everett’s parents, but despite Parker’s best efforts, Meredith is so absurdly, impossibly stiff that it’s hard to believe she has the capacity to connect with another person enough to even have a relationship, much less one serious enough to inspire holiday travel.

7. Serendipity (2001)

When two people (John Cusack and Kate Beckinsale) meet oh-so-cute trying to buy the same pair of gloves at Bloomingdale’s at Christmastime, they decide the logical thing to do is to write their phone numbers on random items, which they then release back into the world. If either of the items finds the other person, then that’s destiny, right? Spoiler: It’s destiny! It takes them multiple years, a pair of jilted new lovers, and a whole slew of romantic contrivances, but they eventually track each other down again. Peter Chelsom’s rom-com is sweet and light, but not destined to be one of the greats.

6. While You Were Sleeping (1995)

Sandra Bullock stars in John Turteltaub’s While You Were Sleeping as Lucy, a train token collector who has developed a crush, from afar, on a regular commuter. One day she saves him from an oncoming train and then lies, saying she's his fiancée, so that the the hospital will let her see him. Keeping up the charade for his entire family, Lucy spends Christmas with them and eventually falls for his brother. If you hate rom-coms built on One Big Lie, this basically sounds like your worst nightmare — but wait! Frustrating as the premise is, Bullock saves it from being a painful exercise in digging oneself deeper, and she and Bill Pullman (as the comatose man's brother) have authentic chemistry.

5. The Best Man Holiday (2013)

The follow-up to 1999’s The Best Man reunites that film’s ensemble cast almost 15 years later for Malcolm D. Lee’s yuletide sequel. All of the guys (Taye Diggs, Morris Chestnut, Terrence Howard, and Harold Perrineau) are struggling, either financially or emotionally, when Chestnut’s character’s wife (Monica Calhoun) gets the gang back together to spend Christmas at the couple's palatial home. Over a decade later, the large ensemble has kept its chemistry, but while the Christmas setting gives them material to turn into laughs, it also provides more than enough holiday pathos for Lee to spin into over-the-top melodrama.

4. The Holiday (2006)

Two depressed women (Kate Winslet and Cameron Diaz) on different sides of the globe spontaneously swap houses for two weeks at Christmas in Nancy Meyers’ light, charming double-romance, and both unexpectedly (seriously, it’s so very unexpected) find love in their new surroundings. The cast is so wonderfully appealing, and the self-conscious dialogue pops enough, that despite being shamelessly sentimental and rather obvious, this is a Holiday to take again and again.
3. Bridget Jones's Diary (2001)

Opening with Colin Firth in a hideous reindeer sweater and ending with him in an equally offensive snowman tie, Sharon Maguire’s Bridget Jones’s Diary, adapted from Helen Fielding’s bestselling novel, follows a year in the life of its protagonist and is bookended by the holidays. The reimagining of Pride and Prejudice casts a wonderful Renée Zellweger as a contemporary Elizabeth Bennet, smoking, drinking, and journaling her way through her 30s in London. While sometimes Bridget’s talent for humiliating herself is really too much to bear, Bridget Jones’s Diary is still one of the greats — because if there’s any sight on earth that can warm a cold grinchy heart, it’s Colin Firth and Hugh Grant trading blows in the middle of a snowy London street.

 

2. Love Actually (2003)

Billed as “the ultimate romantic comedy,” Richard Curtis’ Love Actually follows nine overlapping love stories — not all romantic, and not all happy — in London in the weeks leading up to Christmas. It definitely can get schmaltzy — the prime minister pursuing his former employee all over the city and then getting caught kissing her in the middle a children’s Christmas pageant comes to mind — but for every creepy cue-card declaration of love (just one, mercifully) there’s a little boy running through Heathrow Airport, and an aging rock star and his manager who realize that their friendship is the greatest love they’ve ever known, and two people who fall in love despite a language barrier and then learn each other’s languages in order to declare their love on Christmas! (Okay, that might be slightly schmaltzy too? But it’s Colin Firth.) Not all of the love stories in Love Actually are created equal, but as a whole — a great big British love-stuffed messy whole — it’s irresistible, actually.

 

1. When Harry Met Sally (1989)

The worst movie on this list was about New Year’s Eve; now the top spot goes to another romantic comedy that culminates in the beginning of a new year. Rob Reiner’s classic, from a script by the incomparable Nora Ephron, follows Harry (Billy Crystal) and Sally (Meg Ryan) as they meet just after college and then become friends and eventually fall in love. The pair has perfect chemistry, the dialogue is endlessly quotable, and New York is more real and more beautiful than rom-coms usually bother to make it. In short, when Billy met Meg, the genre was never the same — and when he told her “I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible,” on New Year’s Eve, the holiday was launched to romantic new heights.

 

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