Tim Heidecker Doesn’t Mind Getting Serious

Tim Heidecker doesn’t love traveling, but he loves touring. He enjoys living out of a bus, waking up every morning in a new town, even showering at the venue, living light, living on his toes.

“I don’t really like vacations,” says the 48-year-old comedian-musician-actor-writer-producer, whose multi-hyphenates alone could attest to that fact. “It’s like, all right, what do I do? What museum am I looking at now? The work I do is so fun that I don’t have to kill time looking at statues in town. I like the work, I like hanging out with people, I like the camaraderie. I don’t need to go to any museums anymore.”

It’s late August, and Heidecker and I are chatting backstage before he and his band, the Very Good Band, play one of New York’s annual SummerStage concerts in Central Park. They’re slotted in between sets from budding Brooklyn-based singer-songwriter Fenne Lilly and certified indie favorite Snail Mail. After tonight’s gig, they’ll hit the road, opening up a string of shows for Waxahatchee. (Heidecker’s chief musical collaborator and bassist, Eliana Athayde, also plays bass with Waxahatchee.) 

There’s a chance that, even now, some might be surprised to find Heidecker on these kinds of bills. He’s still best known as an alt-comedy legend thanks largely to his work with Eric Wareheim, as well as On Cinema with Gregg Turkington. But since 2016, he’s released five albums of vintage singer-songwriter fare, using music as a vehicle for explorations of nostalgia, grief, politics, heartbreak, and aging. He’s worked with Weyes Blood, the Lemon Twigs, and Mac DeMarco, and both indie sensation MJ Lenderman and critic’s favorite Nate Amos (Water From Your Eyes, This Is Lorelei) have cited his albums as an influence.

“I should hope so!” Heidecker cracks of the impact he’s had on this new generation of indie rockers. “I’m waiting for a flood of those kind of quotes.”

His next album, Slipping Away (out Oct. 18 via Bloodshot Records), uses a “before and after the fall” framing to balance some of Heidecker’s most fun and freewheeling work, and some of his most pensive and apocalyptic. It opens with a charming portrait of writer’s block and closes with a landscape of impending doom (albeit with a glimmer of hope, courtesy of a coda sung by Heidecker’s daughter, Amelia). In between are songs about awkward marriage proposals and baseball, work and family, societal collapse and pervasive dread. 

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“My job the past eight years, or whatever, has been to try to push my audience to have a more open mind about what you’d expect from me,” Heidecker says. “I feel like it would be more rewarding if [as a fan] I happened to like a comedian and their music. I think that would be cool.”

Slipping Away is also Heidecker’s first album with the Very Good Band. He assembled the group through recommendations, and some played on his previous records; but it wasn’t until they all first toured together in 2022 that they coalesced as a band. Their presence in the studio made for a more fruitful and collaborative process, Heidecker says. And also — just as important — “the hang was more natural and fun. I wanted that feeling of, like, the drummer’s laid his parts down, but he’s gonna hang out for the rest of the day and have lunch with us.” 

During our conversation, Heidecker spoke about Slipping Away, the challenges of embracing sincerity, how his musical career has developed and flourished, the end of the world, and why his next record might need to be funny.

Where did this album begin for you?
The first tour I did with the Very Good Band, Ellie [Athayde] brought an acoustic guitar along. It was a practice guitar that I picked up backstage and started playing. She said, “There’s a lot of songs in that guitar,” which is a very poetic thing. It was the song “Hey, Would You Call My Mom for Me” that I [first] started writing. 

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What were some of the challenges of making this record?
I think it’s whenever I break into full sincerity mode, full vulnerable writing mode. I’m uncomfortable doing it. I know my audience is going to be uncomfortable [laughs], or they’re unsure whether or not it’s a joke. But I still do it. The biggest example is ending it with this thing from my daughter. I was like, “Do I really want to go that deep into this serious, emotional thing? Is it cringy? Is it corny?” But I got the support of my band and the guy who made the record, Ian [Doerr]. Some other people. They were like, “It’s pretty, it’s cool, we get it.” 

Your past albums have gone into that mode, but the back half of Slipping Away is very bleak and heavy. Did it feel like you were taking it a step further?
Definitely. That’s been the progression — it’s been out there and it shouldn’t be shocking if you’re into it. But there are people that don’t want that. I want to. In my acting, my writing, my music, if I have an idea that doesn’t necessarily fit into the box of comedy, I don’t want to not explore that. There were apocalyptic thoughts happening in 2022 and ’23, and I love those kinds of shows, movies, and books. So I wanted to explore writing in that mode.

What were some of the apocalyptic things you were drawing on?
It’s in my bones, my DNA a little bit. There’s a couple Leonard Cohen songs that I connected with. With “I Went Into Town,” I was like, let’s see if we can get that “Famous Blue Raincoat” feeling. The Talking Heads’ “Nothing But Flowers” was a big one for “Bows and Arrows” — it felt like the opposite of that song. I was watching The Last of Us. I’m watching The Leftovers right now; it’s so fucking good.

How is that feeling in your DNA?
I grew up at the end of the Cold War, on Red Dawn and War Games, and nuclear annihilation. It’s always been a very real possibility in the modern age. And I guess traveling around and seeing certain places post-pandemic, where things hadn’t come back to normal yet. Things were not going well. It seems to be getting better, but at the time of writing, it just felt like, what’s next?

When did you hit upon this “before and after the fall” structure?
A fair amount of the bleak, narrative-driven story-songs came first, but I didn’t want the record to be overwhelmed with that. I had some other songs that felt like they could be a setup. There’s a character — who’s always me, essentially — at a crossroads of middle age, thinking about family, thinking about life. But there’s something worse coming, something changing. That’s the last song on the first side, “Something, Somewhere,” and then it’s like something happens when you flip the record. 

Tell me about writing that song.
On that tour, I noted this melancholy feeling when you’re doing something, like a tour, and you look at the schedule and you’re past the halfway point. It’s like the end of summer when you’re going back to school. I just hadn’t thought about how that’s a real feeling. I guess there’s a name for it; the Germans probably have a better name for it. But this nostalgia, this melancholy. You know that scene in The Sopranos when Tony is in the coma and there’s always that light? I was thinking about that scene and the idea of this dream-feeling of something bad’s coming. I feel that way every morning when I look at my phone to see what I missed in the news. 

What’s it’s like having fans connect and form relationships with your music? Is it different from how people have connected with your comedy?
There’s not a lot to relate to, necessarily, with the comedy. You can love it and be a fan of it, but this is much more personal and I think people are connecting to it on that level. I’ve been doing this long enough that I’m letting people know it’s OK to not be drenched in irony all the time. We can still have fun. I still want to laugh. But it’s OK to cry or be moved or talk about real stuff. And I think it’s important, especially for men, to have that allowance. Give them the permission to be like, “We can be upset about something, or moved by something, or feel the need to reach out and talk about stuff.”

The album opens with “Well’s Running Dry,” a song about not not being able to write a song. How do you deal with writer’s block, doubt, or insecurity in your creative practice?
I definitely go through periods of doubt and dryness of ideas — it’s natural. There’s a perception of me as very prolific, which isn’t always a good thing. I just make a lot of stuff. I always go to this Paul McCartney quote, “Work begets inspiration.” Just start making something. Something good’s gonna come out of that. 

That song’s also a tribute to the band. Because it’s not so much about coming up with good ideas, it’s about being with these people and playing music — that’s what I love to do… I need people around. I need an audience. I need collaborators. The solo part of this is the least fun part.

That makes for an interesting contrast with “Bottom of the Eighth,” which turns a trip to a baseball game into a meditation on work, committing to a dream job, and trying to hold onto what you love even if success is fleeting or elusive. 
Absolutely. I love baseball, clearly, and it’s similar to entertainment: Your expectations better be low for this life — even lower for baseball or sports. It’s such rare air at the top. So you better like playing baseball, whether you’re making a living at it or not. Same with this. I know where I’m at and I’m grateful for what I have. But of course, there’s moments where you’re like, “Why don’t I have that status in the world?” But I think we all go through that cycle of thought.

Satisfaction can be hard to accept, and you don’t want to confuse it with complacency.
Right. I’m doing this tour, which feels like a step down in a way because it’s a support role, but it’s like, people are gonna come and maybe there’s gonna be a new audience out there not expecting it. Expectations are really important to keep in check. 

It’s been eight years since you released In Glendale, which kicked off this songwriting journey. How do you think you’ve grown or changed as a songwriter?
I’ve gotten marginally better, I think. I know where my pocket is. It’s still a mystery, though. I don’t know where these things come from. I don’t know how I can write a three-chord song that hasn’t been really written before. I just don’t know how that works [laughs].

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I haven’t written a good song in a while, since this record. There’s a few I’m working on. But I like that it goes away completely and then something will come, and that will inspire three more songs. 

Do you feel like songwriting has been an exercise in allowing yourself to be more sincere? And do you think you’re reaching a point where your audience is expecting it and ready to engage with it on its terms? 
I will be anxious about it always, and we’ll see how this tour goes, how the reactions are. There’s certainly funny songs I can play, and I can break the ice with that stuff. I mean, the next move, to be honest, is probably to do something that’s just overtly funny [laughs]. Just remind people that I still love doing that. Eric and I want to make another Pusswhip Banggang record, which we did years ago. Making music is so fun, and I don’t want to get pigeonholed into like, “I’ve got to write soul-searching, heavy, end-of-the-world music for the rest of time.” I want to go wherever I feel inspired at the moment. I always try to think about, how can I subvert expectations? And right now it’s been going into the serious realm. But I don’t want people expecting me to write serious music for the rest of my life, either.