Comedian and musician Tim Heidecker hit the road last summer for his Two Tims tour. It featured two acts: a stand-up comedy set by his alter ego, “Tim Heidecker,” a hacky, misogynist idiot; and live music by the real Tim Heidecker & The Very Good Band. His diary of the tour, From the Bus, is one of the three mini-books that make up McSweeney’s 72. Our website editor, Chris Monks, caught up with Tim recently to discuss the book, his music, and his comedy career.

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CHRIS MONKS: From the Bus is the first thing I’ve read by you that isn’t in the voice of one of your personas. Was it refreshing writing it, given you’re often writing absurd, exaggerated versions of yourself?

TIM HEIDECKER: I let my real self sink into my music as well as a bit of my personal life on Office Hours. For a few years, I’ve been writing a weekly blog for patrons, and it’s been therapeutic and fun to find my voice through journaling. I think Nick Cave, and his Red Hand site, has been helpful in feeling more comfortable putting down the pretense of irony every once in a while.

CM: In the book’s intro, you write how you were inspired by Donald Fagen’s tour diary Eminent Hipsters. What in particular do you like about his memoir, and how has Steely Dan influenced your songwriting?

TH: Fagen perfectly captured the subtle and grinding annoyances of tour life, and made it funny. While I still love the road, I expect to grow weary of it in my later years. And, yeah, Steely Dan was huge for me in my late thirties and early forties. They, along with Randy Newman and Warren Zevon, reminded me you can make serious music without losing your sense of humor.

CM: Growing up, I considered Steely Dan my parents’ music, but now I have a real fondness for them. What is it about Steely Dan, in particular, that so many people gravitate to them in their thirties and forties?

TH: They weren’t that big in my growing up. I don’t think my parents really cared about them all that much. I just knew the hits and that famous sample of “Peg” in that Arrested Development song, which I remember just loving. In my thirties, I started digging into the singer-songwriter movement of the seventies and found so many gems that never got a lot of radio play. That just led me down a long road of great music, and Steely Dan was all over it. I think their humor is something that often gets lost, their irony—it’s really great. Also, their mastery of the studio. The records just sound so good, and I don’t think that’s something you really can appreciate as a younger person. Or it’s certainly not something I appreciated.

CM: From the Bus includes many funny details about the day-to-day minutiae of touring, from the meals to the accommodations to the struggle of finding adequate bathrooms. I found it all oddly enthralling, probably because I get nervous about traveling and logistics in general. How did you handle the stress of all of that?

TH: I’ve been touring for about fifteen years, once every few years, so I’ve gotten used to the lifestyle and learned what’s important and what you just accept as the reality of the situation. My tour manager for many of those tours, JP, is just really, really good at it, as well as being a good and fun friend to be around. He does his best to make things as pleasant as possible. There’s a trippy exhaustion that sets in, but there’s also wonderful adrenaline that comes with live performing that balances it out. The stress for me comes from worrying about everyone else, their health and safety.

CM: Early in your music career, you said you had to convince folks it was not a bit. And throughout the tour, there are times when you’re concerned about audiences navigating between the two Tims. Is it tiring having to manage expectations and explain which “Tim Heidecker” you currently are?

TH: No, it’s not tiring. I’m always expecting people to miss the plot, and when they dial into it, I’m just grateful.

CM: How does your comedy writing influence your songwriting, and vice versa? Or are they two separate processes?

TH: I don’t know if they influence each other, but they both come from the same brain, so I think my comedy ideas often have some dark seriousness baked in them, and the music also has some funny twists and turns here and there. The process is similar in many ways—a germ of an idea forms somehow (that I don’t really understand!), and it’s worked over privately until it’s ready to present. It’s then brought to a partner or collaborators and gets crafted and worked on until I’m really happy with it. I’ve always said that the collaboration is the best part. When the partnership is working, it’s pure recreational fun.

CM: You’re very prolific, with multiple comedy and music projects in the last few years, and now a book. How do you juggle all the collaborations? How do you decide which ideas to do with which writing partners?

TH: It’s pretty organic and natural. There’s just people I vibe with and people I don’t. If I’m feeling excited about working with someone, I will try to make that happen, and often it doesn’t, for all sorts of reasons. It all stems from trying to approach these projects from a place of playfulness. It’s what I’d want to be doing with friends.

CM: The relationship you’ve cultivated with your fans, whether through Tim & Eric, On Cinema, or Office Hours is pretty unique, as they participate to the point where they often feel like part of the act. They’re intensely all-in on the many different inside jokes and memes. On Cinema-heads are particularly committed to the bits and hilariously engage with you and Gregg Turkington online. Was audience participation something you intended when you first started doing the show, or was it more organic and took on a life of its own?

TH: I don’t think it was ever the intention, but it’s a nice bonus. We sometimes discuss ideas in terms of how they will play with our audiences, but it doesn’t really change how we approach them. I agree it’s special and unique as far as I can tell.

CM: You mention in the diary that, now that you’re older, your comedy has veered away from ironic detachment. Is that a product of your comic sensibilities changing over time, or does the current state of the world also play a role?

TH: I still love playing in irony, parody, satire, and exploring damaged, awkward relationships (see my latest interview with Kyle Mooney), because it’s all forms of playing. I think I’ve just learned to not make that all I’m about, because you can get very cynical and boring if you limit your creativity to one specific lane. Some have done it masterfully, but it doesn’t work for me. I’m too antsy.

CM: That’s one of the things I love about On Cinema, how your character changes from season to season. The show’s new season just started, and “Tim” has reinvented himself yet again. What inspired this latest version of him?

TH: It’s now becoming a process of elimination where we ask, “What haven’t I done!?” This Tim (now known as “T. Amato” on the show) has taken on a multilevel marketing, entrepreneurial vibe, inspired by a lot of grifter-seeming YouTubers. Most glaringly, this new awful person, Patrick Bet-David, and his crew of goons.

CM: Are there plans to get back on the bus and tour this year?

TH: I don’t know if it will involve a bus, but I’m doing a few weeks in the late summer with Waxahatchee and Snail Mail—where I’m one of the openers, or “support,” as they say in the biz. Bigger outdoor venues—it will be a different experience as I know there will be a mix of fans and people who don’t know my musical side, and it’s my job to win them over!