What Is My Problem?

I gave music my best shot. Starting in 1998 and 1999 (when I recorded, released, and re-released Playing God) through late 2003 (when I started business school), I wrote probably 40 songs per year, took every gig I could get, participated in songwriting showcases, attended conferences, hired publicists and radio promotors, and pursued every angle I could think of to establish myself as a singer/songwriter.

It’s not like I didn’t have opportunities. I made my first two albums with Tommy West, who produced every Jim Croce song and dozens of other hits besides. Tommy struck a licensing deal with Sliced Bread Records, the Philadelphia label that released Playing God and championed it to an extent I couldn’t. I was selected for prestigious showcases at the Telluride Bluegrass Festival (4 or maybe 5 times) and the Rocky Mountain Folks Festival (twice), where I was exposed to all sorts of people, including an agent named Sean Laroche, who had connections because he’d worked for Frank Barsalona at Premier Talent in the 70s and more recently at Fleming, Tamulevich, and Associates, who booked many of the top folk and singer/songwriter acts of the day. With Sean’s help, I opened for established artists on the East Coast listening room circuit and way beyond: Club Passim, Iron Horse, Tin Angel, Birchmere, Ram’s Head, Club Helsinki, Club Cafe, Freight and Salvage, etc. Through songwriting associates, I became friends with Suzanne Vega, who carted me around the U.S. and Europe on a long tour that included venues like the Fillmore and Shepard’s Bush Empire and led directly to a spot at the Newport Folk Festival. Toward the end of that run, Suzanne connected me with Judy Collins’s label, Wildflower Records, which might have been willing to help me get to the next level if I’d stuck with it. I had the same lawyer as ZZ Top, for crying out loud!

Here’s one issue, though: I had great people helping me – Sean Laroche became one of my best friends, and Tommy West was a father figure – but not all of them could go the extra mile. Sean, for example, was semi-retired and suffering from various ailments. He also had other clients, including Mary Gauthier, who started to break around that time and commanded a disproportionate share of his time and energy. Tommy had been a gigantic success, but was never a mover or a shaker; rather, he was a homebody who had to be lured into the city from his farmhouse in rural New Jersey. In short, I didn’t have an Albert Grossman: a dynamic, highly-motivated dealmaker who could hustle around drumming up interest and making things happen.

I probably should have convinced an industrious friend to help, because I was in no way equipped to make things happen myself. First, having majored in English and generally resisted any kind of practical orientation in my academic and professional life, I lacked frameworks and inclination to think strategically about my career. Second, I’ve always gravitated toward purists like Jack Hardy, who espoused art over commerce with evangelical ardor. Thanks to Jack, I developed a “write more, better songs” mindset that has served me well. On the other hand, I was taught to disdain self-promotion. Literally, we sat around deriding “peddlers” who cared more about hawking their wares than creating great wares.

I don’t mean to set myself up as some kind of idealist, holed up in a railroad apartment with a crust of bread and an acoustic guitar while my peers sold themselves in the dark alleys of folk music. I sold myself to the best of my ability, but had limited ability. Not so limited, though, as to be totally incompetent. If my music was good enough, wouldn’t it have sold itself? The fact is, my music wasn’t right, or at least wasn’t ready. Take, for example, the 7th track from Playing God:

I took the title, List of Enemies, from the end of the 7th line of the 8th verse of a Dan Bern called Estelle. His song was discursive, insightful, and brilliant, while mine was tightly centered around resentment and revenge. It’s not a bad song in the folk/rock vein, and possibly funny…if you assume I’m writing from the point of view of character or Randy Newman-style untrustworthy narrator. But I wasn’t doing either of those things! Rather, I was expressing anger, which is what a lot of my songs did at the time, including Spitting Nails, When I Wrote the Book, and Everyone’s An Actor in New York, which are 2nd, 4th, and 5th on my debut album. I had nice songs too – e.g. Little Things, I Turn Slowly Around, Witchcraft Lover, and $100 Bills – but they were kind of weird and may have been subsumed into the vortex of negativity.

I recall one late-night song circle at the Kerrville Folk Festival when I busted out List of Enemies with the support of a like-minded friend. Every song had been gentler and more optimistic than the last, and we’d had enough. Where was real life? In our defense, we were the New York Boys, and could claim a gritty existence relative to the rural Northeasterners and Texas hill country wanderers who comprise the folk community. It was part of our branding! That’s all well and good, but List of Enemies went down like a lead balloon and must have contributed to my earning a problematic reputation. In fact, when I went back to Kerrville a year or two later and re-introduced myself to one songwriter/musician whose friendship I aspired to, he pointed and said “I remember you…ANGRY SONGS!”

Another issue along the same lines is my sense of humor: people don’t always register the deadpan aspect of what I’m doing, which can be catastrophic. Once, after playing a particular song at a gig in Delaware that was strange in many ways, a listener came up to me and asked for a free CD. When I said no, he responded with pointed criticism: “Your first song sucked. I couldn’t tell if you were joking!”

Actually, misinterpretation has been a through-line in my various careers. At Clorox, I received formal feedback that people couldn’t tell when I was joking in meetings; I introduce myself to my Little League teams by explaining that frowns and glares may or may not reflect my state of mind. I even invented a game called “Is Coach Bob joking?” as a vehicle for examples: “This season, the three coach’s kids will always bat first, second, and third, and playing pitcher, catcher, and shortstop. Is Coach Bob joking?” Trust me, they don’t always know.

I’m still deadpan as hell, but I have ways of dealing with it in songs and on stage. For example, I might push my lyrics to the point where only a crazy person could be serious. Does anyone really believe I’m as ecstatically pro-Trump as a singalong called Dystopian Hellscape might purport?

On stage, I will sometimes allude to impending humor in a song introduction, if there’s risk of regrettable misunderstanding. But I’d prefer not to have to explain. Instead, I set up humor with humor. For example, I might signal a mood by starting with a short, improvised song about being the opening act – customized to the situation, undeniably kooky – and then follow with I Think I’ve Taken Enough Shit From You This Year, which works best when you understand its comedic intent from the beginning. This technique can generate unintended consequences – such as when I follow a funny song like Canadian Border Fence or Don Jr. in Handcuffs, Crying with Celebrating Nothing or Cocaine Ruins Everything, which seem funny at first but turn out not to be funny at all – but generally gets the job done.

One thing I’m very deliberately not doing anymore is writing angry songs. That’s not because I don’t feel anger, though I’ve mellowed significantly in the last twenty years. But when I address something that pisses me off, I take a more enlightened tack: instead of complaining or accusing, I explore. Shiny Silver, for example, could have been a bitter rant against rich white men. Instead, I tried to imagine what the characters might be thinking and feeling. I even try for empathy in my Donald Trump, Jr. song: “Also, we could see that the ordeal was terrifying/Don Jr. in handcuffs, crying.” In my opinion, this approach minimizes confusion/revulsion, but also – more importantly – generates songs that are deeper or at least more multi-faceted than a lot of my early songs. It’s a whole new way of writing, and it’s working for me.

I probably could have figured all this out earlier. Valentine’s Day and Tolstoy have a lot in common with recent songs, and they came out on Welcome to My Century in 2001. Why didn’t I pursue that path? Probably because I didn’t actually identify the path, but rather stumbled to and fro along various paths like most of us do. Who knows if it even would have made a difference, given the many active variables including luck? Be that as it may, I’m making up for lost time by exploring in songs to the best of my ability and selling myself in positive, authentic ways. Who knows, maybe it’s not too late to make it in show biz…