Holiday romantic comedies ranked
7th December 2018

‘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. As part of our Countdown to Tinseltown celebrating this festive season, we’ve ranked 14 of the genre’s entries from the last 30 years that bring holiday cheer as much as romantic wish fulfillment. Check out our countdown ahead.

14. 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.

13. 200 Cigarettes (1999)

200 Cigarettes, like New Year’s Eve, is a very bad ensemble rom-com with a very great ensemble — this time including Paul Rudd, Dave Chappelle, Courtney Love, Kate Hudson, Ben and Casey Affleck, and Janeane Garofalo — that intertwines a bunch of New York stories on New Year’s Eve. Risa Bramon Garcia’s late-90s effort just edges out the later film, however, because when it comes down to two movies with no personality whatsoever, indie mediocrity will always have at least a sliver more soul than glossy studio schlock. So congratulations, 200 Cigarettes. A happy new year to you.

12. 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.

11. 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.

10. 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.

9. 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.

8. Last Holiday (2006)

When she receives a terminal diagnosis right before Christmas, Georgia Byrd (Queen Latifah) quits her thankless job and blows her savings on her dream European vacation. With the focus primarily on Georgia’s personal journey rather than her shy romance with a co-worker (LL Cool J), Wayne Wang’s rom-com is somewhat low on love story and high on predictable contrivances. But who are we to complain when Latifah’s clearly having so much fun?

7. 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.

6. 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.

5. 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 — especially the ever-winsome Winslet — and the self-conscious dialogue pops enough, that despite being shamelessly sentimental and rather obvious, this is a Holiday to take again and again.

4. You’ve Got Mail (1998)

The charm of Nora Ephron’s late-‘90s classic is so great that even 20 years deeper into the digital age, You’ve Got Mail still never fails to imbue the dial-up tone with the thrill of romantic possibility. With Tom Hanks and Meg Ryan’s legendary chemistry at its height, the antagonistic relationship between them — he as an executive at his family’s chain of mega-bookstores, she as the owner of an independent bookshop threatened by his company’s success — sparkles even more than their email romance. Points off for it not strictly being a holiday movie, but its vision of snowy New York has enough of the spirit for it to make the list.  

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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