I Saw 10 Ships: The Best Christmas RomComs

When you think of what children’s Christmas movies are really about – elaborate holiday fantasies about befriending Santa, visiting the North Pole, and getting the ultimate present – it’s a wonder that any kids like them at all. Real life never matches up.

You could say the same thing about holiday rom coms. I don’t know why I love watching attractive people fall head-over-heels in love (right in time for Christmas!) while sporting designer wardrobes. I could die alone in clothes from Target, but that won’t stop me from loving a good Christmas rom com. If you love rom coms too, make some time between now and 12/25 to see these three ten ‘ships come sailing in.

Traci’s Picks

Love Actually

What’s a Christmas movie list without Love Actually? Shit – is what it is. I remember going to see this with some friends in high school (at the theater Molly used to work at!) and immediately loving it about 10 minutes in. I was enamored with Christmas in London, hot Karl, Jamie and Aurelia’s unspoken love story, ‘Ifyou real-ly love Christtt-mas’ charming Prime Minister Hugh Grant, pre-fame Chiwetel Ejiofor & January Jones, everything about Emma Thompson, SAM – all of it. I bought the soundtrack and played it on repeat, even when it wasn’t Christmas. Needless to say, it’s not only one of my favorite Holiday RomComs, but all time movies in general. Besides Crash, Richard Curtis brought the intersecting storylines way of filmmaking into the the 2000s, and it’s been an influence on movies ever since.

The Best Man Holiday

Let’s be real. I only went to see this movie theater because of the impressive amount of HBMs (<- click for explanation). I hadn’t see the first one, but I figured I didn’t really need to know much about it, and they would recap me if necessary. And if you haven’t seen it either, the good news is that when you watch The Best Man Holiday, they’ll do just that. This group of longtime friends gets together for some quality time over Christmas, and while there are many laughs and near panty-dropping moments (like the one shown above), all I’m telling you is to watch with a box of tissues next to you. You will probably need them.

I’ll Be Home For Christmas

I wasn’t one of those girls into JTT. Just call me the 1%. I was too busy fangirling over Leo and BSB, I didn’t have time for a silly crush on a 90s It boy. However, I wasn’t exactly immune to his movies either. Like this one, a fun and festive adventure which has JTT speeding across the country in a Santa suit to get from California back home to New York in time for Christmas. Yes, that is Jessica Biel as his girlfriend. Yes, of course, the ride in a one-horse open sleigh together.

Bad Santa

Does this really constitute as a romantic comedy? Maybe not entirely, but these is some ‘romance’ in it, thanks to my girl Lauren Graham and her naughty relationship with Billy Bob Thornton’s Santa. He’s a disaster, but you know who really wins Christmas in this movie? THIS KID.

When Harry Met Sally…

When Harry Met Sally doesn’t entirely take place over the holidays, but a chunk of it does, and of course the end at New Year’s Eve, so I’m counting it. If you’ve read my previous post about this film, you’ll know that I was a late bloomer to this amazing movie, but I’m all in now. WHMS is a reminder that New York at Christmastime is a magical beautiful place – and then you snap back into reality watching Sally try to haul a Christmas tree by herself in the snow down the street. But all of it, the good and the bad, is a reminder why RomComs like this are the perfect thing to watch at the holidays. They make you laugh, make you cry, make you all tingly inside knowing that the season isn’t just about the trees and the snow and the presents – it’s about being around the people you love.

Molly’s Picks

The Holiday

The Holiday is one of my top two Christmas rom coms (it sort of shares first place with Love Actually). It has everything I could want in a Christmas movie: aspirational real estate (both the California mansion and the Cotswolds cottage), just-as-aspirational hair and wardrobe, precocious English tots, a kindly old man, and Jude Law right in the middle of what will someday be remembered as his golden era. Sure, it does fall into the romcom trope of everyone thinking the obviously pretty and charismatic Kate Winslet is some sort of sad sack, but – spoiler! it turns out she’s leading lady material after all. With Jack Black and Cameron Diaz rounding out the main cast, the Holiday is the perfect balance of rom and com.

Meet Me In St. Louis

As with regular-season rom coms, it’s important not to disregard the classics at Christmas. This musical (come on, you knew there would be a musical!) follows a year in the life of a turn-of-the-century family. However, the film ends at Christmas time, and is the origin of Have Yourself A Merry Little Christmas. To be honest, I never would have bothered with this movie if (1) I weren’t in the play in 8th grade, and (2) it didn’t star Judy Garland while she was still … doing well. But it’s worth watching if you like musicals, holiday cheer, and one of the most talented performers of a generation.

The Family Stone

I recommend this rom com with one reservation: I am recommending the whole thing except for the last, oh, five-ish minutes. If you’ve seen it, you know why. But the rest of it is great, sort of a Yuletide This Is Where I Leave You. And like TIWILY, it’s at least somewhat relatable if you have a large family of grown siblings, in-laws, nieces and nephews. The comedic parts of it hit a little harder than a lot of Christmas movies, which stick to the feel-good fluff. Plus, the cast is incredible: Christmas King Dermot Mulroney, as well as Diane Keaton, Craig T. Nelson, Luke Wilson, Sarah Jessica Parker, Claire Danes, Rachel McAdams,  Elizabeth Reaser and Paul Schneider (Mark Brendanawicz himself).

But I mean it about the last 5-10 minutes.

Elf

Elf, a rom com? I say that it is! It may be a children’s/ family movie, but I think it’s one of the funniest films out there. And I know I’m not the only one who thinks so, because just about every other adult I know can quote the whole thing. After a rocky start (the musical Law and Order: SVU episode setup that is Baby It’s Cold Outside), the gentle love story of Buddy and Jovie is a big part of what makes Elf so sweet. What can I say? Smiling’s my favorite.

While You Were Sleeping

If I had to explain to someone what 1995 was like, in the romcom world anyway, I’d show them While You Were Sleeping. This movie is just so delightfully normcore, before we had a word for it. Everyone’s hanging out in Chicago, wearing Gap sweaters and Land’s End khakis, telling lies about their romantic history and falling in love during comas and stuff. If you’re wondering why your mom still calls Sandra Bullock America’s Sweetheart, just watch While You Were Sleeping.

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Unexpected Stars of Elf

In November of 2003, I was a teenaged movie theater employee. In addition to sneaking ‘courtesy cups’ of popcorn and Oreo Cream Blast (TM) every shift and taking my friends to free movies, I’d pop into theaters during my breaks to watch some of the better films [ and sometimes, you know, Confessions of a Teenage Drama Queen or whatever.] I probably saw Elf five times during that ’03 holiday season – albeit in 15-minute snippets. Ten years on, I still love it just as much. Yes, it’s hard to believe, but Elf — eminently charming, extremely quotable, and in my view, one of the best Christmas movies of all time — was released ten years ago this month.

Everyone knows that Elf had some amazing writing and a great soundtrack, but I think the ensemble cast is a big reason that it holds up so well a decade later. Everybody knows Will Ferrell’s Buddy, of course. Elf was also one of the first times anyone noticed a pre-bangs Zooey Deschanel. There are others that everyone will remember: James Caan, Bob Newhart, Edward Asner, and Mary Steenburgen. But did you realize that all of these folks were in Elf, too? Some of them have been around for decades, and others became famous since Buddy took the journey through the seven levels of the Candy Cane forest, through the sea of swirly twirly gum drops, and walked through the Lincoln Tunnel.

Peter Dinklage — Miles Finch

In Elf: Dinklage played Miles Finch, a grumpy children’s book author and – in Buddy’s view – an “angry elf.”

Outside of Elf: These days, Peter Dinklage is earning major accolades for his work in Game of Thrones. You may also know him from his work as Marlowe Sawyer on Nip/Tuck, Stewart on 30 Rock, and my favorite, Peter Drunklage on SNL.

Faizon Love – Buddy’s Manager

In Elf: He’s the hardworking, exacting Gimbel’s manager who insists on six inch ribbon curls and wants to know why Buddy’s smiling like that. He would like Buddy to make work his new favorite.

Outside of Elf: Love has an extensive resume, mostly character work. Shane in Couples Retreat? That was him. The Perfect Holiday (a Queen Latifah vehicle)? Jamal. Reaching back to pre-Elf times, Faizon Love was Wendell Wilcox on The Parent ‘Hood and Big Worm in Friday.

Amy Sedaris — Deb

In Elf: Deb is Walter’s secretary, who likes to whisper and has such a pretty face, she should be on a Christmas card.

Outside of Elf: Sedaris, of the Comedy Sedarises, has a delightfully nutty sense of humor. My favorites are her Jerri Blank on Strangers with Candy, her great books on entertaining, and all of the stories in her brother David’s books where she wears wacky wigs and fatsuits to freak out their father.

Meghan Black — Elf

In Elf: Brief but memorable role in the Cotton-Headed Ninny Muggins sequence.

Outside of Elf: She’s Atlanta on Clash of the Titans, Misty on Dead Like Me, and Kat on Edgemont. I don’t watch any of those, but a lot of people do.

Michael Lerner — Fulton

In Elf: The children’s book editor who affirms that even with those two pages, the book would have sucked.

Outside of Elf: You’ve definitely seen Lerner in one of his roles as a classy older guy. For instance: Mel Horowitz in the TV show version of Clueless, Rollie Simone on Hill Street Blues, and Arthur in Hart to Hart.

Will McCormack — Witness

In Elf: Just “Witness.” I seriously cannot remember Will McCormack being in Elf, for all the times I’ve seen it. Time for a re-watch!

Outside of Elf: Ethan in Brothers & Sisters, Skillz in Celeste and Jesse Forever (which he co-wrote with his ex, Rashida Jones), Robert O’Connor in In Plain Sight, and he’s directing an upcoming Chris Messina flick. Not too shabby for an unnamed Elf character.

Andy Richter — Morris

In Elf: Morris worked for Greenway Press, which between James Caan, Amy Sedaris, Peter Dinklage, and Andy Richter, is probably a lot more fun than the publisher I work for (which is GREAT don’t get me wrong fire me).

Outside of Elf: Andy Richter is best known as Conan’s sidekick (/Amy Poehler’s older brother). He’s also been a recurring actor on Arrested Development, voiced plenty of animated projects, appeared as Stan on The New Adventures of Old Christine, and had a memorable role on 30 Rock’s Ludachristmas episode (/Tina Fey’s older brother).

Leon Redbone — Snowman

In Elf: A snowman in the style of 60s Christmas specials, who keeps it real (“You’re 6’3 and had a beard since you were 15,” he tells Buddy).

Outside of Elf: You probably already know that Redbone wears a felt hat and big sunglasses, and has an oldtime-y, Vaudeville-y vibe, But did you know that his real name is Dickran? Dickran, is his name. Rough.

Jon Favreau — Doctor

In Elf: The doctor who doesn’t have any cotton balls any more.

Outside of Elf: I guess this is technically still quite Inside of Elf, but he directed it.

Peter Billingsly — Elf

In Elf: He informs Buddy that he’s pretty off-pace with that Etch-a-Sketch business. It’s almost like he was b0rn to be in Christmas movies.

Outside of Elf: Ralphie in A Christmas Story; an adult man who has to hear “you’ll shoot your eye out kid!” every time he is just trying to run to the grocery store to buy a damn carton of milk.