That McEnroe cover for your album Ad Out. When did you know you wanted that image as a cover?

For readers who might not understand the reference, I’ll explain that “ad out” is a tennis score called out by the server or judge when, after deuce has been reached, the receiver is one point away from winning the game. Many of the album’s narrators, I thought, were like those servers, beset but not defeated. (For balance, the album also has three songs whose lyrics might be called domestic realism, sung by happier characters loosely patterned after myself.) Anyway, Leo Mason’s photo of McEnroe lying exhausted on the Wimbledon grass seemed in the spirit, so I asked the artist Jacob Allers-Hatlie if he could use the photo as a model for a cover painting. I originally imagined the figure’s McEnrovian features would be obscured, but Jacob was right to keep them pretty much intact. Jacob’s a lot younger than I am and was hardly familiar with McEnroe, and I think that distance—like a game of telephone—made the cover image more interesting.

I really loved Amateurs, to the point when the movie The Wife came out I thought you should get royalties. You write cinematically. Is that a conscious decision?

I should say that Meg Wolitzer’s The Wife, from which the movie was adapted, came out about a decade before Amateurs, so probably the royalties should trickle in the other direction. I read and admired another of Wolitzer’s novels but didn’t read The Wife, and for better or worse I avoided stories about ghostwriting while I was working on the novel. Though my novel tells a different sort of story, it is tied to the history of women being uncredited or undercredited for writing or contributing significantly to work attributed to men, a history handled with more depth by writers other than I. I tried not to trivialize the issue. Regarding cinematic influences, I haven’t written with an eye toward a long-shot adaptation, but film has so pervasively changed how we see things, it’s hard for me to imagine a scene without at some point framing that mental image cinematographically. Also, Amateurs draws loosely on romantic comedy, from Jane Austen to Hollywood, though I was carefree with the form. These acknowledgements made, my novels contain a lot of interiority and time-hopping of the type easier to manage on the page; I reckon they’d struggle on the screen. In light of that, directors and studios should know that I’m willing to sell rights on the cheap.

I have such fond memories of your “Governor of Fun” early music career. Do you still roll out that moniker on occasion or is it retired for good?

Thanks for going way back! I’ve demoted myself to Country Commissioner of Fun. It hasn’t caught on. One advantage of obscurity is that audiences don’t loudly demand old material, and I’m keener to play songs from the last eight or nine years, things I’ve written since returning to music after a long break. But I still like “Governor of Fun” and am prepared to play it, though it has one note (A4) now out of my range on all but the best days.

You are such a diverse artist, between music, writing — books and criticism — visual art, and more. Does inhaling art in all forms fill you up creatively or do you ever feel overstimulated and just need to zone out for a while? Does either tack work better in finding your own ideas — filling your curiosity or emptying your mind?

If you’ll forgive the self-indulgence, it might be easier for me to answer this question with some—perhaps too much—personal history, then conclude with an attempt at self-analysis. I don’t have aptitude as a visual artist, though for some reason I’m not ashamed to post my childlike drawings online. It’s really just two things, music and writing, and those have been linked for me since I was a teenager. Back then, while spending most of my fast-food and bag-boy money on records, I read music criticism almost exclusively and aspired to be a music critic myself, though I didn’t take many practical steps to realize that goal until much later. I had also taken about a year and a half of piano lessons and had learned basic guitar chords from my stepfather and from Mel Bay instructional books. But I wasn’t a disciplined or even a fully competent musician; I thought of myself as a fan who sometimes wrote songs. My music career, if that’s the word for it, started when at nineteen I made a cassette of my mostly jokey songs with Al Lehman, Terry Eason, and other musicians who were a bit older and much more proficient than I was. They introduced me to Pat O’Brien and Steve Parker, and we started playing rock shows. I carried on with different bands throughout the nineties and got more go-getting, put out records with indie labels, and did some touring, but I was never able to professionalize playing music in the conventional sense, by which I mean I never made money on it.

Writing, then, was a return to something I’d long wanted to do, but it was also a practical shift. A more practical shift would have been to move into a field with brighter prospects than journalism. So maybe I was a failed musician who became a critic, but before that I’d been a failed critic who became a musician; I’ve tried to subvert cliché through circularity. Those first years working as a writer were exciting: I was reading ambitiously, learning from editors and style manuals and from writing a lot on deadline. My wife and I were both working long hours while raising our son through his babyhood and toddlerdom. Our floors were covered with Cheerios, which mice ate fearlessly in daylight. I liked and still like writing for newspapers and magazines, but by 2006 I missed making up stuff from scratch. On top of that the old-model alternative weeklies were fading, so there weren’t as many paying outlets for the sort of informal criticism that best suits me. I left an editorial position to freelance as an editor and writer, and to try to write fiction. A few years later, my first novel spurred me to return to writing songs.

Another key part of this story is that my wife, Nina Hale, has always supported my work. With much determination and brilliant instincts, she turned a solo internet-marketing operation into a mid-sized advertising agency, now employee owned. That eventually generated enough money for us both to devote more time to noncommercial creative pursuits. In addition to her work in advertising, Nina designs and sews clothes, upholsters furniture, serves on boards, and works on projects that occupy a space between craft and conceptual art. For my creative work, I’ve joked that with talent, perseverance, and 25 years of spousal patronage, some things are possible. There’s some truth to that, but the other truth is that we have this joyful, harmonious, mutually supportive marriage, and we inspire each other.

At times, such as when entertaining regret-based fantasies while jogging, I’ve wished I had been single-mindedly disciplined and ambitious, worked more exclusively and uninterruptedly on songwriting, fiction, piano playing, criticism, or what have you rather than periodically shifting my focus. Possibly I’d be further along in one of those areas. I’d also be a different person, so my actual self wouldn’t get to enjoy all the resulting status and virtuosity. In real life I try to work with care on whatever seems most compelling and feasible at the time. Moving back and forth between concentrations has had advantages. For instance, writing—and reading more critically—has made me a more careful and maybe a more distinctive lyricist than I was before.

The different forms do give me access to different ideas—or different vantages on the same ideas—but I’m more aware of the different skills they employ and develop. I like crafting and revising sentences and analyzing things in prose, which is tricky in song, though right now I’m trying to conceive a musical project that would let me write more prosaic lyrics. I also like melody, harmony, and playing with and learning from other musicians, and I can’t do that in a novel or essay. It’s psychologically convenient to think one is always getting better, but I do think I’m getting better, or at least I’m excited about projects that prod me to try new things. With songwriting, I’m not a technically advanced musician, but I’ve enjoyed slowly improving on the piano, teaching myself more music theory, and trying to disrupt my pop songs slightly with a few unexpected intervals and harmonies. It’s a pleasure to work with other musicians who help realize and enrich the songs. And though I’m still fumbling, I’m getting better at notating and charting my songs with these fancy pencils I learned about from a memoir by the jazz pianist Fred Hersch. That’s become one of my favorite things. I’m also excited to be working periodically on music criticism again and feel sharper in that area, though I’m no longer equipped to write much about contemporary pop.

I became an Invisible String Band fan after reading Amateurs. Have you heard from others that you’ve turned them on to bands after reading your books?

I’ve heard from a few fellow ISB fans, but I think you’re the first to tell me they were steered to their music by the book. They can be polarizing, so maybe others were steered but unconverted.

Writing books and recording albums are no easy feat. When do you know that you have an idea worth following up on and spending hundreds of hours – and sometimes years – on?

I’m not sure I do. I frequently have ideas that seem like they could bear fruit and sustain my interest, but many of them don’t. Some of those abandoned ideas are poorly conceived (contrived or overreaching or at odds with my actual skills), but many just come at the wrong time. I think it helps to have inexhaustible material, stuff you won’t quickly tire of and will never resolve, but you could probably find that in any material if you dug deep enough. In any case, the novels didn’t sustain my interest because I had novel premises (I didn’t) or original and coherent ideas I needed to convey; the sustaining ideas were essentially aesthetic, and tautological: I have an idea for a book, and the idea is the book itself. A few years in I could tell the books would in fact be finished but wouldn’t be what I’d imagined, a little less than I’d imagined, frankly, but still satisfying. I want writing to be fun, engaging, and challenging; if it’s compelling me to come back to it, and if I suspect it won’t be universally tedious to others, I trust it’s worth pursuing. Of course, one’s own interest, though essential, isn’t a reliable indicator of quality, and I suppose that’s where it helps to develop a detached editorial mindset, and to take advantage of guidance form perceptive editors.

The albums are different in that, while I might strive for some thematic or procedural coherence, they’ve so far all been collections of autonomous songs. Some of the songs might take a week or two to write, some will come together in a day or two, and some will be written in stages: maybe I’ll set aside a verse for a later date when I have more time or motivation to finish. In any case, no one song results from a serious time commitment, and the rejects aren’t long mourned. Sometimes I have to professionally record a song before I realize it’s not up to scratch, and alas sometimes I don’t fully see a song’s defects until after I’ve released it. For an album, I’ll aim to write sixteen to twenty songs, record thirteen or fourteen, and pare down to ten or eleven.

I loved how much your characters in Boarded Windows seemed to live inside art and their own influences. You give the reader quite an education in a multitude of genres and forms. I loved that you created a musician in the book named Bolling Greene and even put out an album of his (your) songs. Did the writing of the book help you unlock musical ideas to put into the album?

I had something on an intellectual awakening in my late twenties and early thirties—I went back to school for part of that time, but it continued even after I dropped out yet again to work at City Pages, and I’d say I was pretentiously and haphazardly electrified by books and ideas in the way college students sometimes are. I had always been passionate about music, so maybe that lifelong interest in music and this alleged intellectual awakening that preceded the novel’s composition made me want to write about characters who were trying to live through and as art. I also wanted the book to somehow feel like a country song. While working on the manuscript, I came up with some of the Greene character’s song titles and lyric fragments. After the manuscript had been submitted to publishers, I turned some of those fragments into songs. About half the album’s songs are unfaithful covers, in some sense, of Greene’s songs, while the rest derive from the novel in other ways or use some of its images, phrases, or themes. (Themes such as … loneliness.) Conceptually, it could be tighter, but it was a fun way to write. I often like coming up with strategies that create a few layers of distance between me and the song. A forthcoming album, Munson-Hicks Party Supplies, has some of that layering in that it’s a set of my songs written in character and mostly sung by my friend John Munson. We did the basic tracking with guitarist Zacc Harris and drummer Richard Medek, and several very cool guests joined us for some songs.

You submitted monthly puzzles to the Paris Review for years. Do you still do puzzles?

That was a fun gig, though I was running out of ideas around the time an editorial change at the Paris Review Daily hastened the column’s demise. I haven’t written puzzles lately, but I’ve been fooling around with songs written under constraints: a melody whose intervals come from my immediate family’s birth dates, for instance, and a lyric that follows the alphabet—“All because Cheryl didn’t …,” and so on, though that’s not actually a lyric I’m working on. Of course, rhyme is a constraint, and I generally use it in song.

You turned me on to a lot of great theater during your time as a critic for City Pages. Do you still see a lot of theater?

I’m glad I led you to see some good shows when I was on that beat—I didn’t bring hard-won theatrical expertise to the position and regret some of what I wrote, though I did see a lot of great productions and mostly enjoyed the deadline work. I’m afraid I haven’t been seeing enough theater to comment generally on the scene, but I still like seeing shows, and John Munson and I have been working on and off on a musical. A few of those songs are included on the album I mentioned above.

Are you more an introvert or an extrovert in your creative life?

The writing is more necessary to my happiness, though every creative project I take on is designed with some sort of audience in mind, and I don’t think I’d be motivated to write without the prospect of an audience, however small. I love playing with other musicians and am lucky to have played with so many good ones. Solo shows can be cool, too—I miss the group interplay and the rhythmic drive, but it can be a good way to draw people into the songs. When things are grooving during a show, I’m very happy, and onstage and off I often have an entertainer’s instincts and insecurities, but I don’t hunger to perform all the time. Granted, my audience isn’t widespread, and I’m not working tirelessly to expand it, so attractive gigging opportunities aren’t coming in hourly and internationally. Lately I’ve been performing here and there as a sideperson with Lucy Michelle—that’s a fun way to play in public without being responsible for the draw.

How important is a sense of irreverence to your work? It seems to be embedded in just about everything you’ve done, which is a rare thing. Your work has a bit of Harry Nilsson in it and few people attempt or can pull that off.

I was raised by funny people, and I think I have an intractably seriocomic worldview. I’ve written some merely or defensively jokey stuff, and some things that aren’t deliberately funny, but the work that feels truest to my sensibilities is funny in spots but not chiefly out for laughs. I’m flattered that you brought up Nilsson—I wish I could sing like him! He was witty but soulful, too, and his music was as interesting as his lyrics—I’m not a great talent like that, but I’ve loved him since I was a boy, and his is the sort of blend I’m after even when I’m taking cues from different influences.

You’ve mentioned how it’s important to you that your work give off a feeling to the reader/listener and how that has equal importance to you as plot. Who inspired you to approach writing that way?

As a reader I’m mostly drawn to style, wit, intelligence, discernment, depth of feeling. I do admire masters of plot—Dickens or Jane Austen or suspense novelists such as Ross MacDonald—and I want a story to be soundly and elegantly constructed, but I don’t exactly read for plot. I rarely remember them. If a book is tightly plotted but badly or blandly written, or if I find the prose otherwise off-putting, I’ll quit. Likewise with nonfiction—unless I have to learn something and know of no better-written alternative. I read a lot of essays and criticism, and I’m sometimes drawn to work that blurs the line between fiction and essay. Lydia Davis, Thomas Bernhard, and Nicholson Baker are among the writers who influenced Boarded Windows. With Amateurs, which is more plotted than the first book, I was especially thinking of British comic novelists such as Barbara Pym, Muriel Spark, Evelyn Waugh, and Penelope Fitzgerald.

With songs I try to balance narrative or emotional clarity with what I hope will be evocative abstraction. And a lot of lyric writing is about the sound of words, how those sounds facilitate singing and support the melody, and sometimes how they serve the rhyme scheme.

Photos courtesy of Wilson Webb.