For over a decade, singer-songwriter Ingrid Michaelson has ended each year with a Christmas concert in New York City dubbed her “Holiday Hop.”

2020 marks the 14th annual show in this festive, fan-favorite, and always lightning-fast-to-sell-out one-night-only holiday event. Of course, COVID-19 has prevented this year’s show from being an in-person experience at Manhattan institutions like Terminal 5, The Town Hall, (Le) Poisson Rouge, or City Winery like in years past. But a global pandemic can’t crush Michaelson’s infectious holiday spirit, and like any showbiz professional, she’s determined for the show to go on.

As a result, this year’s iteration of the Holiday Hop will be occurring virtually on Thursday, December 10 at 8:00 pm EST (purchase tickets here!). A combination of pre-recorded and live segments, the show promises to provide all the comfort, joy, rapturous humor, and gorgeously vast holiday music that have become synonymous with the Holiday Hop—this time with attendees all around the world enjoying from the comfort of their own homes. And like last year’s show, this year promises a slew of guest appearances from guest musicians such as Jason Mraz.

To celebrate the upcoming event, I chatted with Michaelson about the enduring legacy and appeal of her Holiday Hop, how this year’s show will be different even for those fans who have attended every year, her favorite memories from 2020, upcoming new music, the musical theater adaptation of The Notebook that she is writing the music and lyrics for, and much more.

Ingrid Michaelson Holiday Hop 2020

This year marks the 14th annual Holiday Hop. What is your favorite part of putting on this show every year?

I think my favorite part is that no matter what, whether or not we’ve been touring, I get to do a show with my band. They’re such good friends of mine and they don’t all live in New York. We all get together and we have a few days of rehearsal. We get to hang out and then we have an after-party and we all get to be on stage again. It’s just so fun. I love it, and now it truly is a tradition. I mean, 14 years, that’s a tradition! There’s something really lovely about just knowing that at the end of the year, we’ll always have this time.

I also always love that we get to dress up like older people from Staten Island and do crazy, ridiculous parody songs and open for ourselves. That’s got to be one of the biggest delights of the Holiday Hop. I’ll explain it as if you don’t know what I’m talking about, but generally speaking we’ll have an opener—a regular wonderful opener—but we’ll also have one before that. So there are two openers, and the very first opener happens right after the doors open. Generally speaking, many people don’t really always see that opener (the first of three) and we dress up in snazzy track suits with gray wigs. We play characters named Eden, Edna, and Ethel who are grannies from Staten Island. We do parodies of pop songs – like one of our very first ones was “I Kissed Santa and I liked it” instead of “I Kissed A Girl.” But it’s not just pop songs, we’ll also do parodies of traditional Christmas carols. It just gets more and more ridiculous every year and we have so much fun!

I blow my voice out every year during that set and then I go backstage while the second opener comes on and does their set. In that time, I have to have my hair and makeup redone, get my dress done and warm my voice back up because I just go crazy. So a really, really fun part of the show is that we just get to be so, so silly.

Why do you think attending this show has become such a holiday staple for your fans, many of whom return year after yar?

I think it’s just fun! It’s pure joy. It’s one of my favorite times of year and it always has been ever since I was a kid. I’ve been given a few opportunities to turn my back on the holiday season. I lost both my parents over the last few years, and every Christmas that’s come about without them, it’s been like, “Well, I can choose to be sad or I can choose to be joyful and be thankful and keep this feeling that I’ve had since I was little girl.” I’ve always actively chosen the latter and this year is the same thing. It sometimes gets hard to choose joy, but the other option just doesn’t even seem like an option to me.

When we knew we couldn’t do this show live this year, I was like, “But everybody loves coming to the show!” I have people that have been coming to the show for 13 years. I have people that have been coming for one year. I have people that have been coming for seven years. There are also people all over the world I’ve heard from that are like, “I wish I could go but I can’t because I live in New Zealand.”

So the idea of not having one this year was just going to be so disappointing to us. I think people need tradition and joy, especially now more than ever. Those are two things that the Holiday Hop always offers people. Now that we’re doing it virtually, it’s awesome because it can reach that person in New Zealand. It can reach these people that might not have had the opportunity or the finances to come across the world or the country to see us.

The Holiday Hop is a really joyful, happy, and positive time. I definitely feel like our energy on stage as friends and as bandmates is electric and people can feel that. And while we’re not in the same room this year, you definitely still feel the friendship and the love between my bandmates and myself in these videos that we’ve done (as many of them are pre-taped).

I’m also going to do a couple live songs in front of my Christmas tree, just me and my ukulele, because I want to keep that live feeling there. The ones that the band and I did, we built the track. As we were doing it, let’s say Elliot’s laying down the drums. He filmed himself while Chris is doing the bass. He filmed himself while he was recording it. When I did my vocals, and when everybody else did their vocals, we also simultaneously recorded ourselves because I didn’t want to lip sync. I wanted it to be that we are doing this live. What you’re hearing is what I’m singing, you know?

Yes, I had it mixed and mastered and some reverb thrown on it, but there are definite imperfections and it’s got a very live feeling. It’s been really great to see it come together. Our editor had an amazing time. He made every song feel different and every video feel different visually. Actually, my boyfriend, who’s an actor, has taken this time that we’ve had off to get really into film, so he has all these great cameras and lighting boxes.

Oh, cool!

I know! But he just got a job and he’s leaving in January. I was like, “Well, how am I going to film myself now?” I’ve gotten so used to this star treatment. But it’s going to look and sound really great. We are totally doing Edith, Edna and Ethel. We are dressing up like old people and singing crazy silly songs. We outdid ourselves, I think, on some of these, so we’re still doing that.

And the livestream will be available for 24 hours afterwards to make sure people from time zones all over the world have the chance to tune in!

I feel like Edith, Edna and Ethel are going to have technical difficulties logging on.

Well, you might be right, but they get it once they’re in!

I have to tell you that I’ve been to the show 11 times and I was so happy and relieved to learn that it’s still happening virtually to this year. To your point, I feel like holiday cheer and traditions might feel needed more than ever this year. I think your fans are going to be so grateful that the show is still going on.

What? Wow, thank you! Well, see, you’re the reason why I want to do it. You answered your own question! It’s a tradition. It’s funny, joyful and sweet and it marks the holiday season. We need these tent poles because every day just bleeds into the next.

Truthfully, I was never not going to not have it happen. I was like, even if it’s just me on my laptop doing a StageIt or whatever, we’re going to do something—and then it just became this much bigger production than I thought it would ever be.

I’m really happy because I think people are going to feel very satisfied. They’re going to have a good time. It’s not too long. It doesn’t cost that much money. It’s $15 for maybe an hour of joy and entertainment, and then you can go back to watching The Bachelorette or whatever.

Do you feel like this virtual format allows you to try or do any new things that you haven’t been able to do at previous Holiday Hops?

I think it definitely allowed Chris, my music director, to be very nitpicky on everything we played. He was like, “It has to sound right. We can’t just barrel through it,” so it definitely allows for a level of perfectionism that you don’t really get in a fully live show. Sometimes you’ll walk out of a live show and you’ll be like, “Oh, I totally fucked up that whole part. That section, I came in the wrong key.” That’s not going to happen. This time around, there’s no anxiety. There’s no fear that you’re going to mess this part up, which is nice.

I hate to talk so much about Edith, Edna, and Ethel, but we went hard with them this year. It was so funny to actually record these songs in a microphone and then listen to them back. All the other songs that we’ve done for the most part, you can find them on one of my albums. You can’t find “Wet and Mushy Potatoes” on an album anywhere.

Oh my god, that’s amazing. I’m cackling at that one already and haven’t even heard it yet.

That’s one of the songs we are doing and we actually recorded them! There are actual recordings and they’re so funny! Being able to really flesh out these characters was really fun.

For the live performances, the live Ingrid Michaelson band, I didn’t want to go super crazy. I just wanted the visual element to be creative. Like I said, our producer and editor did a really great job in making each one feel different visually with unique effects.

Jason Mraz and I will be doing “Christmas Valentine.” We both did it on a green screen because he’s on the West Coast and I’m on the East Coast, so we had some fun with where we were in terms of the green screen. It looks like we’re side-by-side. Part of me was like, “I don’t want people to think I’m trying to fool them,” but then Jason turns to the left and waves at me. And I was like, “I guess I should turn to the right and wave,” because that’s what he did. So it’s definitely a little funny because at one point my arm goes out and it goes in front of him and I’m like, “How do you do that?”

It looks like we’re really next to each other so I feel like I have to give some sort of disclaimer at some point. I’m going to dart in and out and be live at moments, and I’m going to have to clarify to people like, “Just in case you were wondering, Jason is in San Diego, I’m in Brooklyn. We’re far apart,” but it’s all going to be really sweet.

Speaking of “Christmas Valentine,” the song is now available on all music retailers and streaming platforms. What was the genesis behind this track and what inspired you to write a song that could be played during multiple holidays?

Well, I didn’t think about the Valentine part, actually. If I could, I would write only Christmas songs—but at the same time, I have a very high threshold for holiday music. I don’t really listen to holiday pop music. I mean, I will, but my heart goes to Judy Garland and Frank Sinatra and Nat King Cole and that whole tribe. That’s sort of what I nestle into. That’s why on my Christmas record, Songs for the Season, I wanted to make something that sounded super nostalgic. There’s only one original song on that whole album. I was trying to do more, but I was just like I can’t. I can’t force a Christmas song. It just has to be right!

I knew I wanted to release a single last year so I collaborated with my friend Dave Barnes, who writes amazing holiday music and who has a kind of a crooner-y vibe. So we wrote that song together. We actually wrote “Young and in Love” together also, so I had previously worked with him on Stranger Songs.

That was my wedding song!

What?! Congratulations!!

Thank you!

Thank YOU! That’s awesome and so sweet! You have to send me footage of your dance.

So I knew Dave from that. I just loved the holiday vibe of this record and we wrote it over FaceTime. We work very well together. I was like, “This is so great. I love it, and I want to find a crooner kind of person for it.” I’ve been friends with Jason Mraz for many years now. I texted him and I was like, “Hey, I’m working on this Christmas duet. I think you’d be great on it,” and without even hearing it, he was like, “A hundred percent, I’d love to!” It all came together pretty quickly and pretty nicely.

I always want to have Christmas music out. It’s not like something specific inspired me because I’m constantly inspired. I’m just so picky about what I want to say and how I want to say it. I don’t want it to be cheesy … or if it is cheesy, it has to be a certain kind of cheesy. There’s a whole level. It’s like a labyrinth in my mind.

I can say that currently, Dave and I are working on another one that is going to likely release next year. It’s another original that I love. While there will be more original holiday music, I’m never going to have a full record of just those because the classics are so special to me. A record of just holiday originals is not going to happen because there are already so many good ones out there. I prefer to instead put my own spin on the traditional stuff.

Speaking of original holiday music, your 2008 duet with Sara Bareilles, “Winter Song,” is seemingly becoming a contemporary holiday standard. This year alone, artists like Leslie Odom Jr. & Cynthia Erivo, as well as the Fates from Hadestown, included their own interpretations of the song on their new holiday albums.

What?! The Fates from Hadestown?

Oh, yeah, it’s amazing! Eva Noblezada and Reeve Carney are the featured soloists on it.

How did I not know about this? And I know Eva. She didn’t tell me. Weird! Maybe everybody just thinks just Sara wrote this song. That’s probably what it is.

That’s too funny! What did you think of these new versions of the song and how does it feel to have a song of yours embraced in such a festive way?

Well, Leslie did a solo version of it two years ago, too, which I was obsessed with. Then Celine Dion sang it, but it wasn’t on an album, unfortunately – it was just a little live thing. I was like, “Oh my God. Oh my God!” And now Leslie with Cynthia! He posted that on his Instagram, and I know him, too (because he recorded “All I Want for Christmas Is You” with me last year). When I saw that, I told him that “I hope the ‘Winter Song’ you’re talking about is not somebody else’s ‘Winter Song’!” He sent me a link to it and I was like, “Oh my God, this is amazing!” I was really excited because both of their voices, especially together, are just so ridiculous! They’re both so amazingly talented. And now you’re telling me that people from Hadestown, which is my favorite musical in the longest time, have done a version of it?! It’s immensely flattering and incredible.

I love that song so much. Sara and I wrote it over the internet in 2008, and I play it at least every Holiday Hop. Or if I have a winter tour, I’ll probably throw it in at some point. I especially love that it’s nondenominational, and I also love that it’s kind of sad.

I feel like the lyrics feel especially appropriate for this year, too.

Yeah. “Is love alive?” Definitely.

On that note, 2020 has obviously been a very dark year for a lot of people. What are some of the most positive, uplifting or inspirational things that have happened to you this year?

Well, in general, my niece, who’s going to be three in January. She is such an endorphin high. If I feel sad, I just watch videos of her and I’m instantly happy again. I don’t have children of my own and I don’t foresee that happening. We had her for a sleepover last week and it was just so glorious. But everything involves getting COVID testing, so it’s kind of a labor intensive situation. Therefore, I don’t see her as much as I’d like to. But she brings me just the most incredible joy.

And of course my beautiful, wonderful partner, Will. He’s in the living room right now with two monitors and two Black Magic cameras because he’s been shooting all of my Holiday Hop stuff. He’s getting ready for it. We’re having a cue-to-cue run through this afternoon. He’s very sweet and supportive. We’ve been together every day since this whole thing started. That’s a long time to be with another person and I’m happy to say that we’re doing pretty well.

I also think getting an Emmy nomination (for the song “Build It Up” from the Hulu miniseries Little Fires Everywhere), even though I claim to not love award shows, did make me feel good. I have a love/hate relationship with award shows because I feel like there are so many people that are so great that never see the light of day—and there’s so many people that are crap that do see the light of day. It just feels like everyone’s patting each other on the back. I’m like, “Ugh,” but then of course, when I get one, I was like, “OH! WELL MAYBE NOW IT’S DIFFERENT!”

I’ve always felt kind of like this scrappy underdog who’s been trying to be like, “look at me, notice me, I’m part of this community!” So that made me feel somewhat validated. Or rather, it made me feel validated until I lost, and then I was like, “Nah. Fuck it. I’m back to hating everyone.” So I liked award ceremonies for three months and now I hate them again. But that was definitely a moment that I was like, “Oh, I’m being recognized for work that I’ve done.” It felt really good, I have to admit. That was definitely a very joyous moment.

We also did a Zoom workshop of The Notebook and it was glorious. I have to say that working on The Notebook has truly been one of the deepest joys that I’ve ever had in my work life. So when everything was put on pause, it was devastating. I’m not even an actor in a show who’s been laid off. I can’t imagine what that is like. But I can tell you that from my point of view, I was like, “Wait, we’re not going to have our out-of-town Chicago tryout? I’m not going to be there for two months? Wait, wait. Now it’s not going to happen at all?” It really felt like, “I guess this is the end of Broadway for a while,” you know?

But the last month or so it seems like the tides are turning and we’re seeing lights at the ends of tunnels and having really great discussions and creative meetings. I can’t even properly describe it. This project truly has given me more joy than I’ve had doing anything else in the pop world, literally ever.

How would you say that this unexpected hiatus has impacted the show’s creative development?

It’s definitely given us a lot of time to take a lot of hard looks and make important tweaks and revisions. There’ve been many, many discussions. Without getting too far into it, but with the Black Lives Matter movement having such a moment after George Floyd was publicly lynched, the theater community—particularly the theater community of people of color— were like, “Hey, listen to us. This is what we want. We’re here, too”. Our team had to really take some steps and reexamine several things. We have to and are continuing to answer and ask a lot of questions. It’s been amazing and sometimes difficult, but so necessary.

Luckily, we’re still in our developmental stage because now we can really practice what we’re preaching. We can really dig into a lot of issues on racial equity, safe spaces and hiring practices. I think there’s a lot more that we have to do but we actually have the time now so I’m very grateful for that. I think it will allow us to come out even stronger and more glorious on the other end.

I’m sorry if I’m being vague, I just haven’t really spoken about this publicly yet and I can’t say too many specifics – but I do feel like as white people and creators in the theater, we have a responsibility to uplift voices of non-whites. It’s something we were partially doing but partial just isn’t good enough. It’s given us a lot of time to figure out how to make this the best possible piece in a global sense.

So while I was devastated in the moment when our plans got postponed, now I’m very thankful and appreciative for it because it’s given us the space to do a lot of shifting, growing, and implementing. Now I’m just SO excited to get it back going again! I think and hope it’s going to be really amazing.

To wrap up, are you working on any new music at the moment? If so, will it follow the 1980s-inspired synthpop sound of Stranger Songs or the more traditional singer-songwriter sound of “Build It Up”?

I am working on something! It’s not an album, it’s just a song that I wrote. It’s not 80s synthpop. It’s probably more along the lines of a “Build it Up.” It’s not quite as singer-songerwritery, yet still in that realm. I think Stranger Songs was a bit of a capsule because it was so influenced by Stranger Things, that I don’t necessarily—I’m not saying never—but I don’t think that’s what’s coming out of my brain right now.

But this song that I’m working on right now is something that I’m very excited about. It’s actually being produced while we are speaking, it’s being worked on today. I’ve been listening to a lot of FINNEAS lately, and he definitely embraces a lot of singer-songwriter qualities but sort of infuses that sound with pop. I really love those elements of both. That’s a world that I really like sonically right now.

Thank you so much, Ingrid! It’s always such a pleasure to chat with you and I can’t wait to watch the show on Thursday. Is there anything else that you want to add that we didn’t discuss?

Just that the Holiday Hop is going to be so fun and festive. I can’t wait! Thank you, Alex!

CLICK HERE to purchase tickets for Ingrid Michaelson’s 14th annual Holiday Hop, taking place this Thursday at 8:00 pm EST. CLICK HERE to purchase Ingrid and Jason Mraz’ holiday single “Christmas Valentine,” and CLICK HERE to purchase Ingrid’s must-have holiday album, Songs For The Season.

Ingrid Michaelson Holiday Hop 2020

Alex has been writing for PopBytes since 2011. As the Theater Editor, he focuses on all aspects of Broadway, Off-Broadway, Regional Theater, and beyond. Alex lives in Western Massachusetts and can be found on Twitter at @AlexKNagorski.