What's The Best Holiday Rom-Com? (Small Stakes, Big Opinions)

Summary

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Podcast Summary: "What's The Best Holiday Rom-Com? (Small Stakes, Big Opinions)"

Podcast: All Of It (WNYC)
Host: Alison Stewart
Guest: Rebecca Alter (Vulture staff writer)
Date: December 22, 2025

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Main Theme & Purpose

This episode dives into the much-contested world of holiday romantic comedies, exploring what makes them beloved cultural staples, how the genre intersects with nostalgia, changing cultural norms, and individual taste. Host Alison Stewart and guest Rebecca Alter, alongside calls and texts from the WNYC community, debate and celebrate the best holiday rom-coms—classic and new.

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Key Discussion Points & Insights

1. Why Holidays Inspire Rom-Coms

• Rebecca Alter: Holidays combine rewatchability and a sense of tradition—people want coziness and comfort, dropping cynicism for sincerity during the season.

  “There’s a level of coziness over sexiness. Or the coziness is competing with the sexiness.” (03:02)

2. Defining the Holiday Rom-Com

• Key distinction: It's the holiday setting's unique “coziness,” its ability to ground seriousness and sentimentality, that differentiates a holiday rom-com from other romantic comedies.

3. Breakdown of Major Holiday Rom-Coms

Love Actually

• Always at the top of lists for its sprawl of characters, interwoven stories, and iconic moments.
• Rebecca:

  “Even if it’s not the best movie, it’s the most movie. There are like 15 plot lines to keep track of.” (04:19)

• Discussion about how the film handles outdated stereotypes (notably “the girl who’s always called fat”) and the evolution of cultural norms.

  “When I was watching it for the first time, I probably thought it was like satire because it feels so divorced from reality. But that is also just what I think the early 2000s were like.” (05:44)

• The Britishness (Hugh Grant's “charming bumble-ness”) is central to its lasting appeal.

When Harry Met Sally

• Listener Natalie calls in, lauding its realism, relatability, and classic happy ending.

  “It has a happy ending that made me feel very good.... And it has that wonderful line that the mother has—‘I’ll have what she’s having.’” (Caller Natalie/Jennifer, 06:47)

• Rebecca: The film set a “template” for modern rom-coms by being "so witty, so charming," and "full of these little human moments."
• Noted for its seasonal versatility, spanning from Fall to New Year's.

The Apartment (1960)

• Cited for its blend of drama and screwball comedy, set between Christmas and New Year's.

  “That is just one of the best ever rom coms that also thankfully happens to largely take place in that week between... Christmas Eve and New Year’s.” (09:50)

• Discussion of changing sexual politics and workplace culture depicted in earlier cinema compared to modern films.

Shop Around the Corner (1940)

• Inspiration for "You’ve Got Mail."

  “It’s these co-workers... who work in this little Christmasy shop in Budapest during the Depression... they’ve been writing letters to each other so they don’t know that they are each other’s, you know, crush.” (11:39)

• Highlights the timelessness of anonymous longing and mistaken identities.

The Family Stone

• Noted for its ensemble cast and emotional complexity.

  “I consider Family Stone to almost be like a harrowing drama disguised as a rom com, but it also captures, you know, something very relatable to a lot of people around this time of year.” (13:58)

• Discussion of how holiday rom-coms enable star-powered ensemble casts and become part of people’s traditions.

Bridget Jones’s Diary

• Listener Jennifer declares it her favorite; highlights the Christmas setting and relatability.

  “You cannot think of that movie... without that image of Colin Firth in the reindeer jumper popping into your head.” (17:38)

• Praised for wit, soundtrack, and Renee Zellweger's performance.

Serendipity, Bell Book and Candle, Scrooged, Holiday Inn, While You Were Sleeping, The Holiday

• Listeners call in with wide-ranging picks, revealing the genre’s diversity.
  • Scrooged (Bill Murray): “A lot of calm over rom, but it’s so good.” (19:36)
  • Holiday Inn: “Most important, it yields the greatest Christmas song of all time, which is, of course, Irving Berlin’s White Christmas.” (Caller Matthew/Mark, 19:46)
  • The Holiday (Nancy Meyers): Praised for its production design, especially kitchens; Jack Black noted as a standout romantic lead.

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Notable Quotes & Moments

• Rebecca Alter on holiday rom-com coziness:

  “There’s a level of coziness over sexiness. Or the coziness is competing with the sexiness.” (03:02)

• On Love Actually’s wild tone:

  “Even if it’s not the best movie, it’s the most movie.” (04:19)

• Listener Natalie/Jennifer on When Harry Met Sally:

  “It’s very real. This could happen. I identified with it, I identified with her, I identified with him. And it’s just beautifully, beautifully played out.” (06:47)

• Rebecca on Bridget Jones:

  “Relatable, self deprecating, witty, but still holding onto that, you know, belief and hope for something Jane Austeny and sweeping you off your feet-ish.” (17:38)

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Audience Participation & Community Picks (varied timestamps)

• Listeners mention:
  • The Best Man Holiday (Rom over Com, a bit sad)
  • Bell Book and Candle (chic and holiday-adjacent)
  • Feast of Seven Fishes
  • Beautiful Thing (favorite queer rom-com)
  • The Man Who Came to Dinner
  • While You Were Sleeping
  • Bridget Jones’s Diary
  • Serendipity
  • Scrooged
  • Holiday Inn
  • National Lampoon’s Christmas Vacation (for comedic love subplots)

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Overrated Holiday Rom-Coms (22:17)

• Rebecca: Open about loving “big name” classics but wouldn’t argue if someone called Love Actually overrated.
• Unexpected praise for Christine Baranski’s romantic subplot in The Grinch:

  “I think Christine Baranski’s Grinch character deserves a romantic spin off.” (22:25)

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Timestamps for Key Segments

• Introduction & Setup: 00:09–01:27
• Why Holiday Rom-Coms Matter: 01:27–03:24
• Love Actually & Cultural Critique: 04:19–06:31
• When Harry Met Sally Call & Impact: 06:36–08:26
• Classic Films & Generational Change: 09:41–12:37
• Community Picks/Text Responses: 13:43–15:14
• Bridget Jones Audience Call & Analysis: 16:36–17:38
• Listener Calls: Scrooged, Holiday Inn, Family Vacation: 19:21–21:03
• The Holiday & Why It Works: 21:06–21:49
• Overrated Picks, Elf Reflections: 21:55–22:25

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Episode Tone

Warm, witty, and openly nostalgic, with a sincere love for the comfort food of the holiday rom-com genre, balanced by sharp cultural insight and cheerful audience engagement.

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Transcript

[Alison Stewart]

Foreign.

This is all of it on wnyc. I'm Alison Purr Stewart. You know, there's this person I know who is brilliant, smart, has a high flying job and the minute the calendar turns the holiday season, he, she, they are glued to the Hallmark channel for Christmas movies. You know who I'm talking about. You know those films that are set in a small town where one person from the big city falls in love with the other person from the quaint village. And of course, hilarity ensues. Look, these movies are great for making cookies, wrapping presents, or just curling up on a cold night. The holiday classic romcoms from the Apartment to Love. Actually, everybody has a favorite, even the grinchiest of you out there. So for this next installment of our small stakes big opinion, we're asking the question, what is the best holiday rom com and why? And of course, we want your input on this hotly contested debate. You can call or text us right now. 2124-3396-9221-2433. WNYC what is the best holiday rom com and why? Rebecca Alters, a staff writer for Vulture, who put together a list of her favorite holiday rom coms for us and she joins me now. Hi, Rebecca.

[Rebecca Alter]

Hi. Thanks for having me.

[Alison Stewart]

All right. Why do the holidays, Christmas in particular, make for a thriving rom com industry?

[Rebecca Alter]

I think there's a few factors. One is that both are the rom coms favor rewatchability and repeatability. And something about the holidays, Christmas traditions, carols, movies is you're going to revisit it year after year. You're going to be filled with that warm nostalgic feeling. It's sort of a time of year where you let your defenses down a bit. You're allowed to put cynicism aside for like a month and then you could get back to it if you so choose and indulge in sincerity, which is really fun.

[Alison Stewart]

So I'm going to ask, are you a fan of holiday rom coms?

[Rebecca Alter]

I am. And I think your intro really summed up the beauty of the gamut of it because there are every year the Lifetime and Holiday Hallmark and now Netflix ones that follow all of those tropes. But then, you know, there's some really amazing movies from throughout Hollywood history that are great romances that happen to be rom coms that happen to be holiday rom coms.

[Alison Stewart]

When you're talking about a holiday rom com versus your every average day rom com, what's the difference between the two?

[Rebecca Alter]

Besides, I guess, the time of year when it takes place and how much Christmasy stuff they get into is there's this feeling of like maybe it's that there's. There's a level of coziness over sexiness. Or the coziness is competing with the sexiness.

[Alison Stewart]

Yeah.

[Rebecca Alter]

Versus the average rom com. And I think that that is both. They're complimentary and also delightfully intention. And yeah, there's also, it's that thing of people who say, oh, Die Hard is my favorite Christmas movie. Some of these are mostly rom coms, but if they have a couple of iconic Christmas scenes or wintry scenes, I'm counting them as holiday.

[Alison Stewart]

All right, we got this text. It says hi from the West Village. This is more Rom than calm and a bit sad, but I love the best man holiday. Thanks for texting in, listeners. We want you to weigh in on this high stakes conversation. What is the best holiday rom com and why? What's your pick? Give us a call. 2124-3396-9221-2433. WNYC. It's our edition of Small Stakes Big. What is your favorite holiday rom com? My guest is Vulture staff writer Rebecca Alter. All right, let's talk about some of your favorites. Love, actually, we're gonna start with love. Actually. It's pretty much everybody's favorite rom com. It stars Hugh Grant, Colin Firth, Liam Neeson, Keira Knightley, Laura Linney. Why is this movie always mentioned on everybody's list?

[Rebecca Alter]

I think it's because even if it's not the best movie, it's the most movie. There is so much happening. There are like 15 plot lines to keep track of. It takes wild tonal shifts. There's a really fun couple of musical moments in it and everyone is really committed to giving these great performances despite often deeply, deeply silly material.

[Alison Stewart]

Would this movie work if it weren't British?

[Rebecca Alter]

Well, that's actually, I think a lot, a lot of my favorite Christmas rom coms. Holiday rom coms. I wonder. That very question. I think they just have a knack for Christmas and they do have a knack for that classic Y2K era Rom com. It's that Hugh Grant like, charming bumble ness that you just have to go along with. It's so fun.

[Alison Stewart]

All right, I'm going to take a little bit of attack because sometimes more recently this film has come under fire specifically for how it treats a main character who they. Her family's always calling her fat and all these different descriptions of her. How do you divorce the stereotypes of films from like the 90s a time when we want to forget certain things that have older and outdated ideas. That could be said for a lot of films, actually.

[Rebecca Alter]

Yeah, that is a really good question. And it's especially with that in this movie it's like. It is so ludicrous that they're calling her these names that I think when I was watching it for the first time, I probably thought it was like satire because it feels so divorced from reality. But that is also just what I think the early 2000s were like. But I do think, yeah, with so many. I have a couple movies on my list that are quite old. Yeah. Old movies are going to have moments in them that, you know, if you're watching with your kid or something and they're in that, you know, school age or whatever, it could be an opening for a conversation and. Yeah, yeah. Just don't maybe take your life lessons from romcoms in general.

[Alison Stewart]

Let's talk to Natalie from Manhattan. Hi Natalie, thanks for calling, all of it. Natalie, are you there?

[Caller (Natalie/Jennifer)]

Oh, hello. Hello, Hello, Hello. Are you calling me?

[Alison Stewart]

I am calling you, Natalie.

[Caller (Natalie/Jennifer)]

Oh, yes. Well, my favorite movie is. And I can see it again and again When Harry Met Sally. I love that movie. And the reason I loved it is because it's very real. This could happen. You know, I identified with it, I identified with her, I identified with him. And it's just beautifully, beautifully played out. And also because it has a happy ending that made me feel very good. I was. I understand that originally it didn't have a happy ending and they changed it and I'm very glad that they did. And it has that wonderful line that the mother has. I'll have what she's having.

[Alison Stewart]

Thank you so much for calling in. Yeah. How did When Harry Met Sally change the rom com game?

[Rebecca Alter]

It's what everyone has been trying to do since it came out. It casts such a large shadow because it is so, you know, it feels relatable today as ever. And the ways that they talk and you know, some of it has become cliches that, oh, men and women can't ever be friends. And that whole fight that leads to such perfect little human moments. It's full of these little human moments. And the amazing thing about it is it's a fall movie, it's a summer movie, it's a Christmas movie, it's a New Year's movie. It looms large like with every season. It tackles and it's tackling it all over the years of these characters lives. But they're just so. It's so witty. It's so charming. Even the friend characters are relatable, which is not always the case.

[Alison Stewart]

Yeah. And you know, when you think about When Harry Met Sally, you obviously think about its director, Rob Reiner, who died tragically. What about this movie and the way it's told lets you know that Rob Reiner was involved?

[Rebecca Alter]

Well, even what the caller brought up, the fact that the original ending wasn't even supposed to be happy. You know, it was written by Nora Ephron and she wrote it the way she wrote it, brilliantly written. And then because he. I think he fell in love with his wife during the production of the film and he had to change it or the fact that I believe it's his mother who does the all have what she's having on. So it's so many. He, you know, he was able to bring so much of himself and his loved ones into it.

[Alison Stewart]

This text says, put down the pumpkin spice and grab a Martini with 1958's Bell Book and candle. Kim Novak is icon in it. Go ahead. What were you gonna say?

[Rebecca Alter]

Oh, no, just that that's such a fabulous call because I obviously think of that as default Halloween because she's a West Village witch. The media does overlap with Christmas. I don't remember, but that is such a chic, chic little movie. I love it.

[Alison Stewart]

We'll put one on your list from 1960, the apartment, directed by Billy Wilder. Tell us who stars in this one.

[Rebecca Alter]

That is Shirley MacLaine and Jack Lemmon. And it is just like the ur text of rom coms. This is another. That is just one of the best ever rom coms that also thankfully happens to largely take place in that week between, like, Christmas Eve and New Year's. So they get to claim it. And it has, you know, 60s, like, holiday parties and trysts and a sort of. There's a bit of a dark edge to it as well. But then there's also, you know, some really daffy, goofy, screwball stuff. It's just. It's just one of the best.

[Alison Stewart]

When you're watching a rom com from the 60s versus watching one fairly present, what's changed about the holiday rom com and what has and will never change?

[Rebecca Alter]

Ooh, that's a good question. Well, this is one because it was also. There were just fewer or maybe I don't know if there's fewer being put out or just fewer that have stood the test of time. But now it's hallmark. There's like 80 that get put out a year. So it had a chance to be so, like, inventive in the moment. And I think what has both changed and stayed the same is the sexual politics of a movie like the Apartment coming out in 1960, which is right on that cusp. It was after a lot of code and censorship. So it's about all of these, like, men in the workplace sleeping around with these women in the workplace. But then there's like that heart and that human connection and the way that these main two click and have this, like, respect for each other and. And dig at each other feels pretty modern.

[Alison Stewart]

You also have the Shop around the corner from 1940. What's the premise of this movie?

[Rebecca Alter]

So this is. If you've seen you've Got Mail, it's that it's kind of the inspiration for that or for the musical she Loves Me. So it's this. It's these co workers, it's James Stewart and, I believe, Maggie Sullivan who work in this little Christmasy shop in Budapest during the Depression. And they banter and they don't get along, but they have. They've been dating via, like, personal ads in the newspaper and they've been writing letters to each other so they don't know that they are each other's, you know, crush. And then when he finds out, he can't reconcile it with this annoying co worker of his. So that also feels weirdly, you know, the anonymity of the dating. Yeah. Can be transposed to any era. We can make it, you know, a hinge thing now. But it's amazing to think that even then it was nostalgic for like five years prior to my.

[Advertisement Voice]

Yeah.

[Alison Stewart]

My guest is Vulture staff writer Rebecca Alter. She's here for our next installment of our Small Stakes, Big Opinion series. Today we're asking the question, what is the best holiday rom com? We'd like you to weigh in. What is it and why? Our numbers. 2124-3396-9221-2433. WNYC. I'm gonna read through a couple of texts. Love, actually, for these two specific reasons. Number one, Rodrigo Santoro, Laura Lillamy's Love Heart. And number two, Jody Mitchell's Both Sides Now. Feast of Seven Fishes. Someone else wrote in. Every year my wife and I watch while you were sleeping. Sandra Bullock, Bill Pullman. It's wonderful. My favorite queer romcoms, threesome Jeffrey and Beautiful Thing. And this one says the man who came to dinner not only has big city Betty Davis falling in love with small town reporter, including some 1941 dating insights, but an Alexander Walcott spoof Jimmy Durante and an octopus. That is a great.

[Rebecca Alter]

I'm intrigued and I'm adding all of these to my letterboxd watch list as we speak.

[Alison Stewart]

This one says favorite Xmas rom com. Unpopular opinion, but I totally love the Family Stone. RIP Diane Keaton. That is on your list.

[Rebecca Alter]

Yeah, I mean, I think it was top of mind because of losing Diane Keaton this year. But also it's a rom com that again, like something like the Apartment has quite an edge to it. I consider Family Stone to almost be like a harrowing drama disguised as a rom com, but it also captures, you know, something very relatable to a lot of people around this time of year, which is the going home, meeting the parents, you're home with your boyfriend's family for the first time, or girlfriend's or partner's family, and the million little culture clashes of that. I think it's really fun to see Sarah Jessica Parker play such an opposite type to Carrie Bradshaw. This is a true antihero. This is like a tough protagonist to root for, but I do think it really, really holds up. And I hear they're maybe working on a sequel, so something to keep an eye on.

[Alison Stewart]

When you can think about the cast of the Family Stone. Sarah Jessica Parker, Claire Danes, Rachel McAdams, Diane Keaton, and you think about the cast of Love. Actually, what about holiday rom coms? Allow for these massive star ensembles.

[Rebecca Alter]

I have to imagine. At first, I was gonna say I have to imagine residuals, but I don't know if TV reruns even count for much in 2025. But I think also.

[Alison Stewart]

In.

[Rebecca Alter]

In my fantasy imagined Christmassy idea of Hollywood, I imagine these would be sort of cool, fun sets to be on. I'm sure that's not always the case for some of these. But getting to do the broad comedy, you know, getting to do a scene where it's like the turkey's burning or you're doing karaoke or, you know, just getting to do like a classic rom com scene where you're running to someone at the airport. Love actually has an amazing running to the airport scene. One of the best loving running to the airport scenes it seems. You know, they're. They're light except the Family Stone, which is pretty heavy, but many of them are pretty light and become. They just become parts of peoples and families and couples lives. You get to be something in something that people come to again and again as part of their holiday traditions.

[Alison Stewart]

Let's take a couple calls. Mark. Mark's been holding for a while. Hey, Mark. Thanks for calling all of it. No, Mark. Let's talk to Jennifer in Brooklyn. Hi, Jennifer.

[Caller (Natalie/Jennifer)]

Hi.

[Caller (Jennifer)]

How are you?

[Alison Stewart]

I'm doing well. What's your favorite rom com?

[Caller (Jennifer)]

Bridget Jones Diaries, my all time favorite. And I hadn't thought of it as a Christmas movie, but I always watch it around Christmas and I realized, as you probably know, Mr. Darcy is wearing an ugly Christmas jumper and that's how they meet. So instead of the ball and Pride and Prejudice, there's a whole Christmas thing and that's how they meet. So I just find that also the, the way that, that they deal with the holidays and, you know, single people feeling lonely. And I actually feel like it's a really deep movie that everyone can relate to and all the smarmy couples and I mean, I'm gonna. I'm a smarmy couple too. But, like, you know, I think it's a really wonderful way and it's very real to me. And I think because you guys are talking about love actually, I feel like you. Grant is so wonderful in Bridget Jones. I'm not a big love actually fan, you know, so that's. That's what. That's where my thinking was.

[Alison Stewart]

Thanks for your.

Your call.

That is also on your list of favorites. Why is Bridget Stone Jones Diary on your list of favorites? Rebecca?

[Rebecca Alter]

That is probably my number one too, if I had to pick. Because, yeah, it counts. Because you cannot think of that movie without the or about Christmas and holiday rom coms without that image of Colin Firth in the reindeer jumper popping into your head. But I think that truly has such a wit to it. I find the soundtrack is excellent, even though it's largely not just Christmas music, but overall, really great music supervision on it. And Renee in that lead role is like, you know, it's sad to confess to finding Bridget Jones deeply relatable, but here we are. And also the best American to ever do it in terms of doing an English accent. Like, I don't think it comes close. They send theirs over all the time and do an amazing job. She's one of the few who, like, embodies this type of English character. But, yeah, relatable, self deprecating, witty, but still holding onto that, you know, belief and hope for something Jane Austeny and sweeping you off your feet. Ish. And yeah, Hugh Grant plays an incredible cad in that.

[Alison Stewart]

He plays a great cad. This text says Serendipity with John Cusack, takes place in New York with an ice skating scene and just a general, wonderful holiday magical feel. Let's talk to Shannon, who is calling in from East Brunswick, New Jersey. Hi, Shannon. What's your small stakes, big opinion?

[Caller (Jennifer)]

Probably also one of my favorite Christmas movies and may or may not qualify.

[Rebecca Alter]

In your book as a rom com, but Scrooged with Bill Murray. Absolutely love it.

[Alison Stewart]

It's worth a laugh or two, that's for sure.

[Rebecca Alter]

Yeah, it has a lot of calm over rom, but it's so good.

[Alison Stewart]

Let's talk to Matthew in Great Neck. Hi, Matthew, thanks for calling all of it. What's your opinion?

[Caller (Matthew/Mark)]

Hi, how are you? I'm gonna go back to the. The golden age of Hollywood with the movie Holiday Inn, which when you get down to it, is really a rom com. You have these two icons. You have Fred Astaire and Bing Crosby fighting over, you know, the lead actress. And it's very slapsticky, goes through all these different numbers, but really, most important, it yields the greatest Christmas song of all time, which is, of course, Irving Berlin's White Christmas. And so it's just, you know, romantic comedy. Of course, you know, it goes back to the origins of Hollywood. It's not just our generation. So it's really fun to go back and watch these old Christmas movies and enjoy, you know, the fantastic music and just that old golden era of Hollywood feeling.

[Alison Stewart]

Thanks for the call. And let's talk to. I think we got Mark back. All right, Mark, let's hear what your big opinion is.

[Caller (Matthew/Mark)]

I was thinking of what you call it, the movie with Chevy Chase. Oh, man.

[Alison Stewart]

Family vacation.

[Caller (Matthew/Mark)]

Family vacation. You know, to see Dreyfus and the boyfriend. It has to be some kind of love thing going on. Even though it's on the backside.

[Alison Stewart]

We're gonna take that as a big opinion.

That one.

Thanks. Thanks for calling in. I want to get to one more on your list before we run out of time. You have the holiday down, which is Cameron Diaz, Jude Law, Kate Winslet, and Jack Black. That is an interesting cast.

[Rebecca Alter]

It's an interesting cast. And the. The fact that Jack Black is the one of those four who is sort of the best romantic lead is a revelation and incredible. And also, Nancy Meyers should be doing twice as many holiday movies. She should be putting them out every year because she knows how to design an interior or whoever's on her team.

[Alison Stewart]

Especially a kitchen man.

Oh, yeah, Nancy Meyer's kitchen.

That's the best. I noticed here there is no Elf on your list.

[Rebecca Alter]

Oh, you know, I guess because the rom element with Zooey Deschanel takes that sort of the B plot. Or because I keep forgetting about it because my brain can't really process Blonde Zooey Deschanel, and maybe it makes my brain forget the movie entirely. But that scene where she's singing the carol and he's getting excited, that's very. That's very cute.

[Alison Stewart]

Overrated films, overrated holiday movies. Rom coms that you thought, like it gets a little too much shine.

[Rebecca Alter]

Ooh, probably like I could admit, I'm sure I picked some of the bigger name ones. And if someone were to make a case that like a Love actually is overrated, I can't disagree with them. I'm just gonna say that I still do enjoy it. And also I'll say on the note of Elf, there is I like the romantic component to the Grinch. I really like the backstory that Christine Baranski in the flashbacks seems to have had a crush on young Grinch and vice versa and something went wrong. I would like that to be explored. I think Christine Baranski's Grinch character deserves a romantic spin off.

[Alison Stewart]

Rebecca Alter is a staff writer at Vulture. She was here to help us through our Small Stakes Big Opinion series. We were talking about the best holiday rom coms. Thanks for joining us.

[Rebecca Alter]

Thank you so much.

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