After 20 years, Tim Heidecker’s career remains an enigma of the most delightful sort. 

Rightfully revered as an alt-comedy legend for his work across five seasons of Adult Swim’s seminal "Tim and Eric Awesome Show, Great Job!," Heidecker’s subsequent gigs have included an ongoing 13-year stretch hosting the satirical "On Cinema" podcast (in character) with fellow comic Gregg Turkington, his 2020 anti-comedy special An Evening with Tim Heidecker, and as of Oct. 18, the release of his fifth studio album as a musician. 

Out Oct. 18, Slipping Away is anything but a jokester having a laugh in the studio. Rather, the album is the latest and strongest example of a pivot into sincerity — a journey that's been an adventure for both Heidecker and his fans. 

"For the past two summers, as I've toured, there's been a bit of confusion and snickering and people not being sure how to react," Heidecker tells GRAMMY.com. "But by and large, it's a good group of people who are making the transition along with me."

Speaking by phone from his home in Los Angeles, Heidecker was also quick to offer reassurances that he has no intentions of making things too heavy or moribund on his fall tour, where he’ll be supporting the likes of Waxahatchee and Snail Mail. That’s a serious bill for a funny man, but Heidecker is ready for the challenge. 

"We don't take things too seriously," he says of his music and tourmates. "There's room to have fun — we just also want it to be okay for people to emote and to feel vulnerable. We can talk about our anxieties and fears and then can go back to goofing on stuff a minute later. That's how human beings should be, I think. I like making a big old gumbo of experiences." 

That’s certainly one way to describe Heidecker’s eclectic, beloved and singular output as a comedian. But while his early forays into music may include an undeniably catchy urine-themed Americana song, his last few albums have seen the 48-year-old deal with topics that aren’t always primed for a punchline. Slipping Away touches on everything from climate dread to writer’s block, demonstrating Heidecker's genuine ambitions as a musician in tandem with the talented Very Good Band.

Heidecker spoke with GRAMMY.com about his approach to songcraft, his role as a curator of comedy’s next generation, and how he earned the title of "Dad of the Year" — the name of his new single — by taking his kids to an AJR concert. 

This conversation has been edited for brevity and clarity. 

Before we dive into your fantastic new album, what's it been like to watch the current Republican candidate for vice president seemingly reenact your film Mr. America as his entire campaign strategy? 

Yeah. It's a blast. I couldn't get enough of it. I hope people are discovering that movie. We made it in the era of Trump that we're still somehow in. This has happened before, where we do something on the show and then it kind of happens in real life. 

In some ways, I wish you were worse at it, but immense kudos are nonetheless warranted. 

Yeah, I've got to stop manifesting things into existence. 

Slipping Away isn't the first of your music releases to embrace sincerity as a powerful theme. You've said that, to a certain extent, all your records are concept albums. Given your daughter's vocals are featured on the track "Bells Are Ringing," would you say fatherhood served as a major theme of your latest record? 

For sure. I can't separate my creativity from my experience as a father anymore. When the kids were a little younger, it was easier, because babies are a little more neutral in your life. Of course, that's not entirely true. If you watch season three of "Check It Out! With Dr. Steve Brule," there's a lot of diaper humor going on. If you go back and look at my life post-kids, they've definitely influenced my work. 

Half this record is about mundane, midlife, personal anxieties, and then the second half of the record is way more macro with things falling apart. The record starts in a very grounded place, with normal feelings, and then devolves into more abstract anxieties about the world. 

The lead single, "Well’s Running Dry," deals with the theme of writer's block, which some of your fans may find surprising, given you seem to consistently be involved in a bevy of different projects. Is writer's block a situation you've faced often? 

I think I've always had a different perception of my output than my fans do. I always feel like I could be more productive. I go through periods of feeling like the well has run dry, and I'm a little less disciplined about writing and stuff now. 

Comedy, for sure, has always been a young man's game, I think. It's a little slower these days, and I've gone through periods of feeling not very fulfilled creatively. We all go through it. I think it's natural. It reminds me of a quote from [director and comedian] Mike Nichols that I heard years ago. He said that writer's block isn't a thing because your brain is just processing stuff in your subconscious. You're always working, you're always observing, you're always processing. And then, one morning, during a run or a shower or something, something is going to pop. 

Like the evolution of a thought? 

Yeah. I've got things I'm working on right now, but I also feel like creativity comes in big waves, at least for me. 

A lot of the songs for this record were written in a short amount of time, but then I'll go months without writing a song. Then I'll get a song, and that inspires another song, and it's like a chain reaction. It's a mysterious thing: this world of making things.

You've referred to Slipping Away as "a true group project." How did going into the studio with the Very Good Band help shape this record into its final form?

I've known everybody in the Very Good Band since before we first toured in 2022. I've worked with them as session musicians on other records, but I didn't really know them that well. I just knew that they were good players. When I asked everybody to do this tour, I got to really bond with them. I didn't know I would like them so much, as people, and I didn't know that we would all enjoy playing together so much, but that's what happened.

Going into this record, my desire was to really try to make this a group effort: something that wasn't just people coming in for a day, recording all their parts, and going home. It was like: let's come in every day and approach these songs together. I still ultimately made the decisions, but I really wanted it to feel like we were a band that went into the studio to make a record together. And that's what we did. It was great fun.

I say this about movies and television and stuff: most of the joy and the motivation to do it is getting to hang out and to spend time with people I like. That's what this was too.

How does finding that common spark in a studio compare with the energy of a writer's room when everything is clicking?

I love an audience, whether it's two people or 600 people. In a writer's room, you're performing a lot: you're pitching and you're trying to sell what's in your mind to people to get them on board. That process is the same in the studio. With the band, you're trying to communicate what's inside of you to them, and to get them to take your thing and make it better.

In both cases, it's all about having the right combination of people. If the chemistry is good and the people are happy to be there and the talent lines up in the right way, it's magical.

Just as Bob Odenkirk helped open the door for "Tim and Eric," it's been wonderful to see you champion people like Vera Drew and John Early, who are now blossoming. Where does getting to witness the successes of "The People's Joker" or John Early's latest special rank on the list of things  that bring you the most professional satisfaction?

I am jealous and envious and full of sour grapes for anyone else's success. No, I'm so happy for them. Of course, I don't take full credit at all. I'm so picky and judgmental about comedy and music things, but when I see something that I enjoy, I'm the first to champion it.

Usually, my tastes are not very mainstream. I can't stand when social media gives its attention to something that's already seemingly hugely popular, like "The Real Housewives of Beverly Hills" or whatever. I'm like... but this John Early guy is the funniest thing, or Vera, or whomever it is. I also want to be regarded as a guy who, if you want to look for something to consume, I'll always be here with some suggestions.

You’ve credited David Byrne as a major influence. Is it fair to say that both music and comedy have been swimming in your brain together from the get go?

Oh yeah. I think music and comedy are peanut butter and chocolate. Look at musical comedy: the Beatles are hilarious; the Monty Python guys make good music. I think we all start out wanting to make stuff, and when you're younger, it's easier to make music or to have a band than it is to say, make a movie. Now, of course, it's a little different because my daughter makes movies every weekend with her friends — like they have their iPad and she can edit it.

How you wish to express yourself manifests in different ways at different times in your life. I like going back and forth between those two things and drama and whatever other mediums my self-expression may take. That's what it is. I'm not worried about how things are being classified but more just trying to get you to see an idea in its purest form.

Your "Office Hours" show has welcomed a slew of incredible guests, including many excellent musicians. Between getting to chat with folks like whistler Molly Lewis and touring with the likes of Waxahatchee and Snail Mail, has spending time with these artists changed or shaped your own approach to music?

I'm very grateful that, over the past 10 years, I've been accepted into this group of talented singer/songwriters and musicians, and that I get to collaborate with them and play with them. They see me as kind of a novelty — they understand that I'm outside my comfort zone but they treat me with great respect.

Ellie [Athayde, bassist for Waxahatchee] is the bass player in our band and she's always like, "You you've got such a weird life." Because I'll check in with her and tell her that I'm doing a movie with Kevin Kline or something and she's just like, "What is this life you lead?" They're used to putting out a record, going on tour, then putting out another record out and going back on tour. If they're not on tour, they're writing. I get to play around in so many different sandboxes that I think it's interesting for some of those people to talk to me about what I'm doing.

Does the Very Good Band keep a pee-themed Americana track in their back pocket, just in case the mood calls for it? 

That song is called "Hot Piss" and it's interesting. It's become my "Free Bird" or at least the closer that people call out for from the beginning of the show onwards. Now I'm thinking, "Do I not play that?" And I going to tour and not even play that song? If I remove it from the equation, what happens? To be clear, I've got plenty of songs. That's not the issue. It's just whether playing that song to a Waxahatchee crowd would be a mistake... or is it hilarious?

I think you've got to get Katie Crutchfield to join you for it. Only solution.

Precisely.

Before I let you go, it's so lovely to hear your daughter Amelia's voice on the last track of your new record. What artists or music acts have you two bonded over so far?

That's nice to hear. I'm glad. It was a risk. When I was playing it for everybody, I was like, "You guys tell me if this is too corny or something" but everybody thought it was great.

Recently, we went to go see this group, AJR, that my daughter and my son both love. They play their music constantly in the car. It's not my thing, but it's very clever and well-executed and very catchy. They were coming to L.A., so I pulled my star card and wrote them on Instagram to say we'd love to come to the show. Turns out they were big fans, which is nice, so we got the full VIP treatment. I love being able to offer that the other way when people write me. I'm very happy to put people on the list — it's a fun treat.

We went to see them at Kia Forum, which is the big arena [in L.A.]. They had bells and whistles galore with unbelievable lights and visuals. It was very theatrical. It was so mind-blowing, what they're able to tour and the scope of it. My daughter was just blown away. She'd never been to a big arena show like that before. I have so many videos of them with their brains just exploding as these things were happening on stage. And then she got to meet the guys, and they got a picture together. It was very sweet. I felt like the dad of the year.

What would be a comparable show that you saw at that age?

I saw the Monkees’ reunion tour in 1986. That was my first concert, but they did not exactly have all the bells and whistles of AJR on that tour. There was no VIP section. They weren't even a VIP version of themselves.