Ingrid Michaelson charmed fans with her quirky glasses and ukulele, singing songs about her sweater and the catchiest stream of internal neurosis ever. Fast-forward to her seventh album, "It Doesn't Have to Make Sense," which dropped in August, and the Staten Island-bred singer-songwriterisn't quite as upbeat. Faced with the death of her mother and divorce, Michaelson unapologetically sings about heartache, tragedy and well, acceptance and subsequent joy. She declares it an indulgence in a "myrid of emotions" when she picks up the phone from San Francisco, where she and her crew are about to depart for Alcatraz for a daytime excursion.
You’re on your seventh album. How are you handling spreading out the material into a live show? Especially in the cities where you’ll be doing back-to-back nights?
It’s not easy. It took us a few days of being on tour to figure out what worked, and what didn’t. There’s always going to be those five or six you have to do (“The Way I Am,” “Girls Chase Boys,” “You and I,” “Hell No,” “Be OK”), and then the ones you know are going to get people energized, so you work around that. We have an alternate set for the double night, so it’s not totally the same. It’s nice because we’ll play songs we haven’t been playing for the past two weeks, and like I said, there’s a lot to choose from.
"It Doesn't Have to Make Sense" came from some very sad personal times in your life. Was the songwriting process more therapeutic and natural or was it more difficult to get out and write down?
I wasn’t even planning on writing; it just sort of happened. It took me about a year and a half to finish and I didn’t even know what the album was going to be about — but then, I never know until a record’s over and I look back and am like, ‘OK, so that’s what it is.’ This one is about human emotion, the highs and the very lows of the last few years. I found myself feeling guilty for having these joyful moments, but after talking to people, I decided my mother wouldn’t want me to be so, so very sad all the time. I think the record celebrates every corner of your emotional experience. I was trying to quantify the world and define everything after my mom passed away, so that’s why this record was so different.
Is there anything on the album that’s been particularly difficult to perform live?
I lost my mom about two and a half years ago and much of the record is about her. And there’s one song that’s very, very sad. I played it the first night, but I can’t play it again. It’s too much. You have to figure out what are the songs you can’t physically play for one reason or another live, and that one, I need more time to go by before I can sing it again.
Can we discuss the video for “Hell No,” which is essential you singing the song through a series of Snapchat filters? Was that actually filmed on Snapchat?
Off all the social media outlets, that’s the one that strikes me. You can’t take yourself seriously on Snapchat. And I thought, ‘How funny would it be if we made a video using all of the filters?’ I just woke up each day and was like, ‘So what’s the latest filter,’ and did a couple takes and then edited them all together after a month. It took about two hours. [Laughs] It was very inexpensive. It’s my most inexpensive video yet, and one of my favorites.
And on the bigger screen, you’re due to star in Sam Hoffman’s “Humor Me” with Jemaine Clement and Elliot Gould. Any spoilers?
I have a pretty substantial role so it’s pretty exciting. I play a down on my luck musician and a recording drug and alcohol user. It’s very funny and sweet. I haven’t seen it yet, so I can’t tell you much except that it’s coming up.
Are you a “Flight of the Conchords” fan?
Oh my God, of course. Working with [Clement] was really, really fun.
You’ve been pretty vocal about this year’s election and open about your support of Hillary Clinton. Was there a reason you felt you should speak out this year to your fans?
I don’t think I’m incredibly political. And for my social media presence, I can’t help what I say. It is what it is. I think it’s important to show young people what I think, for sure, but I’m not going to get on a soapbox. The other day in Seattle [during a show], I said I hated Trump and the audience erupted into applause. Usually, I stay quiet on political issues, but this has been such a travesty that I’m not going to shy away from it. We’re in dire times. But it’s looking like it’s going to be good.
Let’s hope so.
I know. I don’t know where my place is. This is the most vocal I’ve ever been, and I’m very honestly anti-Trump. It’s a scary, horrible thing that could actually be a possibility. And that, to me, is terrifying.