Ingrid Michaelson on Her New Holiday Single and When It's OK to Play Christmas Music: 'I Have Pretty Strict Rules'

do not reuse - only for christmas album
Shervin Lainez
Ingrid Michaelson

She'll release the holiday album 'Songs for the Season' on Oct. 26. "Even for me, that feels early," she jokes.

Ingrid Michaelson knows that it's a bit early to be thinking about the holidays. That hasn't stopped the singer -- a self-described "Christmas-obsessed human" -- from already wrapping some gifts and watching Elf. This year she's taking her Christmas craze to a whole new level by releasing a holiday album, Songs for the Season, on Oct. 26 via her Cabin 24 Records. The first single, a rendition of the classic "Looks Like a Cold, Cold Winter," is out today; she's also turning her annual New York-based Holiday Hop show into a 14-date tour, titled Ingrid Michaelson Trio Presents Songs for the Season.   

Songs for the Season -- which includes guest appearances from Leslie Odom Jr., Christina Perri and Grace VanderWaal -- finds Michaelson putting a twist on well-known classics as well as sharing an original track, "Happy, Happy Christmas." And it arrives at a time when Michaelson is reconfiguring her own holiday routine: Until last year, the singer-songwriter had spent every Christmas in her parents’ house opening gifts; now, with both of her parents having passed away, she says she’s trying to find a way to hold on to her favorite traditions of the season. "It was very difficult, because I like things to be the same," she says. "I want traditions to be the same. I think part of me likes to keep the Holiday Hop very steady."   

Below, Michaelson tells Billboard about putting together the album, how she's breathing new life into her covers and when she thinks it's acceptable to play Christmas music.   

You're sharing the first taste of this new album. What are you most excited about?    

I’m just so anxious just to start the whole thing off. I love Christmas time. It’s something that growing up was always really important in my family, and it was just a really wonderful time. We would have a big Christmas Eve party every year. Everybody of different faiths would come to our house. My dad played piano, and everybody would sing Christmas carols and eat too much and drink too much. [Christmas] is kind of like a light. When I’m feeling down, I’m like, Well at least Christmas is coming in four months. This whole project has really been my whole career in the making. I’ve wanted to do this for so long, but I just couldn’t find the right moment within my other projects that I’m doing.

Why did you pick “Looks Like a Cold, Cold Winter” as the first single?

I've only heard Bing Crosby do it. I don’t know why there aren’t more versions. I like it because while this is primarily a Christmas record -- there are eight songs that literally say the word "Christmas" and there are four that don’t -- I wanted there to be a handful of songs where, if you didn't celebrate Christmas or didn't want to hear about Christmas, you could still have something to hold on to. So, that song, to me, is like, Let’s bundle up inside when it’s cold out. It’s a not-creepy, not-predatory version of “Baby, It’s Cold Outside.”

How comfortable did you feel taking on some of the classics?

It’s hard, because I wanted to stay true to that sound, but at the same time, you don’t want to just regurgitate something. You have to put a little bit of your own spin on things. Also, my voice isn’t really a chameleon voice. I just sing the way I sing. I definitely tried to not riff. I paid very close attention to my vocals in a way that I normally don’t. I felt pretty comfortable shaking things up a bit, because I still feel like we were being really respectful to that sound.

Your rendition of “All I Want for Christmas Is You” is a lot more mellowed out.

That one was a song that I wanted to do stripped down. That song is very difficult, it’s very nuanced. There are a lot of jazz progressions in that song. My producer, Dan Romer [who co-produced the record with Saul Simon-MacWilliams], took it and simplified a lot of it. It just lent itself to this more somber [vibe] instead of happy, tied-up-with-a-bow [feeling]. It became this longing, like “I don’t have you, and all I want is you.” And then when Leslie [Odom Jr.] sang it, it was so beautiful. Getting together with him was a dream. I feel like that song is the most modern one on the record. But in simplifying it, it fits with that nostalgic vibe in a way that it wouldn’t have if we had just done a traditional cover of it.

How has your Holiday Hop show evolved over the years?

You don’t want things to change too much. Obviously, with new records come new songs. We always end with “Have Yourself a Merry Little Christmas” with me and my bass player, who has been in my band since 2005. I definitely have songs where I’m like, "We have to do these." And then we’ll throw in some new stuff. We’ll do the ones that everyone wants to hear like, “The Way I Am” and “Be OK” and stuff like that. In some ways it grows, and in some ways it has stayed the exact same. Last Christmas was the first time I didn’t wake up in my parents’ house and open Christmas presents because both of my parents have passed away now. It was very difficult, because I like things to be the same. I want traditions to be the same. I think part of me likes to keep the Holiday Hop very steady.

Do you have a favorite holiday tradition?

It’s so sad, because it doesn’t happen anymore. I adored waking up and going downstairs and being with my family and opening up presents. And it doesn’t exist for me anymore. So last year, my boyfriend’s daughters -- who are 17 and 19 -- slept over, and we woke up, and then my brother and my then-pregnant sister-in-law all opened presents at my apartment. And then my aunt and uncle and a bunch of my cousins and my cousins’ kids and family friends came over. It was like this new tradition that we normally have done at my parents’ house. It was strange, because it felt different, but it still felt really nice.

What about a favorite Christmas song in general?

My favorite Christmas song is “Have Yourself a Merry Little Christmas.” The Judy Garland version that she sings in Meet Me in St. Louis. It’s just the best. Her voice is so untethered, and she’s really a vocal icon of mine. The line that kills me and makes me cry [is] “Someday soon we all will be together, if the fates allow.” Just the idea of hopefully next year, we’ll still be doing this, we’ll still be together -- as a kid, I just would be so destroyed when I watched that. It just stuck with me. I grew up watching old movie musicals. I never listened to the radio. I just watched Danny Kaye, Fred Astaire, Judy Garland and Bing Crosby. That was the root of my musicality. It stems from that. I sing it every year, and I love it.

Tell me about the album's one original holiday song.

Well, the hope was at least to have an original song. I wrote that song maybe two years ago. It was about my mother, who I lost in 2014. It’s obviously quite melancholy, and it’s called “Happy, Happy Christmas,” which is very ironic, because it’s not happy at all. But it is if you really listen to it. The strings in the background are so beautiful -- they just destroy me. A lot of people have someone that they love that is missing around the holidays. It makes holidays a very lonely time and a very hard time for people. I wanted to acknowledge that that exists in the world. There’s also something cathartic about hearing somebody sing the thing that you’re feeling, especially around that time of the year. I felt like it was important for me to acknowledge that, while I do love Christmas, and it is a very special time of year for me, there are also really, really dark and sad moments, too.

When do you think is an acceptable time to start listening to holiday music?

I think people want to wait until -- I say this as I’m releasing a single -- after Halloween. [Laughs] That’s why we picked a song about temperature instead of “White Christmas.” But it’s funny, because we obviously asked around, and you talk to people who do this for a living, and they’re like, “Yeah, you gotta have it out in October.” And I was like, "That’s so early!" Even for me, that feels early. I don’t want to annoy people and put it out in October, but that was the advice. So I was like, "Well, if that’s what everyone else does...."

It can be dangerous to start listening to holiday music because once you do, that’s all you want to listen to until the day comes.

I know! It puts you in such a good mood. It’s funny, because I’ve been listening to these mixes because we’ve been working on it for so long. It’s jarring to be listening to this in June when it’s hot out. And I was like, “This is wrong.” I have pretty strict rules. I don’t watch Christmas movies or listen to any Christmas music [before a certain point]. Like, sometimes, some cable channels randomly will have a Christmas movie on in the middle of the summer, and I’m like, “No, no, no!” I won’t even go near it. I need it to be special. But you know, September, October, November, December. So, I have four months. That’s all I’m asking for.

Ingrid Michaelson Trio Songs for the Season Tour Dates:

Nov 26              Portland, OR                Revolution Hall           
Nov 29              San Francisco, CA      The Masonic
Nov 30              Los Angeles, CA         The Cathedral Sanctuary at Immanuel Presbyterian Church
Dec 3                Denver, CO                  Boettcher Concert Hall    
Dec 5                Saint Paul, MN             The Fitzgerald Theater
Dec 6                Madison, WI                 The Orpheum Theater
Dec 7                Chicago, IL                   Vic Theatre​
Dec 8                Cleveland, OH              Agora Theatre​
Dec 9                Royal Oak, MI               Royal Oak Music Theatre​
Dec 11              Munhall, PA                  Carnegie of Homestead Music Hall
Dec 12              Washington DC            Lincoln Theatre​
Dec 14              Glenside, PA                 Keswick Theatre​
Dec 15              Boston, MA                   Orpheum Theatre​
Dec 17              New York, NY                Beacon Theatre