Holiday Romcoms That Actually, Truly, Completely Bring the Com 

5 Serendipity (2001)

What most people remember about this movie is its incredibly sappy premise: Boy meets girl at Christmastime, girl decides to hide her name and phone number in a random NYC bookstore instead of just giving it to him like a mentally balanced person and boy and girl spend years trying to find each other in a city of eight million people as a result. 

However, the upside of keeping the protagonists apart for so long is that most of the movie is actually about John Cusack’s manic quest to find a woman based on nothing but a department store receipt, which is a far funnier premise. Also, please note Jeremy Piven’s shockingly prescient description of the tech billionaire class here: 

Don’t get me wrong, the movie still manages to cram plenty of sappiness into its 91 minutes, but it’s balanced out by characters like Molly Shannon as the New Age store owner who tries to convince her friend New Age stuff is BS or Eugene Levy as... Eugene Levy, working in a department store. 

Renée Zellweger earned her first Oscar nomination as “a verbally incontinent spinster who smokes like a chimney, drinks like a fish and dresses like her mother,” while Colin Firth plays the unlikely love interest who first said those words I just quoted. That description is precisely what motivates Bridget to chronicle her efforts to pull her #$%@ together via the titular diary. Oh, and this all starts and ends during New Year’s Eve. There’s the “holiday” part; you can stop typing that comment now. 

This is the ideal example of a movie you initially dismiss as a vapid chick flick only to end up glued to it at 2 a.m. after coming across... well, almost any scene and realizing it’s actually very funny. It helps that it includes people wishing and enacting violence upon Hugh Grant, which is always amazing to watch. 

Elf features a guy hassling a woman who is openly disinterested and even hostile toward him until he wears her down and they get married. So to answer your question, yes, it's a romcom. At one point, after they’ve just met, he invites himself into the locker room where she’s showering and creeps her out by singing with her. What could be more romantic than that? 

Okay, you could also make the case that Elf is a thriller, I guess. The “romance” part may be sketchy but the “holiday” and the “comedy” aren’t really in question. If nothing else, this is a touching love story between a pure, innocent man and the very concept of Christmas. Just don’t wear red clothes around him unless you’re the actual Santa. 

Another movie where Hugh Grant gets insulted a lot and, not coincidentally, another Oscar-nominated romcom (for Best Adapted Screenplay, this time). Grant plays a cynical slacker who lives off the royalties generated by his dad’s hit Christmas song, a true banger titled “Santa’s Super Sleigh.” 

His carefree life changes when he joins a single parents support group (to get dates, natch) and befriends the socially awkward son of a clinically depressive woman. His friendship with the boy ends up teaching him valuable life lessons and even leads him to abandon his yearly tradition of spending Christmas getting high and drunk while watching horror films alone. This movie is also noteworthy for being perhaps the only holiday-related romcom to involve Mystikal’s “Shake Ya Ass” as a plot point. 

Basically, the blueprint for every modern romcom, seasonal or otherwise, except for one little detail: They keep forgetting to make them even 10 percent as funny as this one. 

There’s a misconception that if a comedy revolves around a romantic relationship, then including actual humor in every scene might be too much for viewers to handle. This one goes, “Nope, here are some actual jokes, deal with it.” Most scenes are capped with a punchline, including the greatest in any romcom made to date. (Warning: Loud orgasmic, or fake orgasmic, screaming in the clip below.) 

Even the now extremely cliched ending with Billy Crystal running into a New Year’s Eve party to declare his love for Meg Ryan and kiss her is broken up by his random observation about what the hell “Auld Lang Syne” means. Stuff like that makes the inherent absurdity of Ryan falling for Crystal much easier to swallow.

Special mention: Ryan romances Tom Hanks without knowing she’s romancing Tom Hanks in Nora Ephron’s other holiday-set romcoms, Sleepless in Seattle and You’ve Got Mail, which also have plenty of funny moments. 

Another special mention: Die Hard. Yes, it is. And, yes, it is. 

Follow Maxwell Yezpitelok's heroic effort to read and comment on every '90s Superman comic at Superman86to99.tumblr.com. 

Thumbnail: Miramax Films