Waiting on a (Small) Change
Tom Waits and the idea of a pivot
Happy End of Seasonal Depression to all who observe! Perhaps now that the sun sets at 7:00 I can pretend I have more time and use that time to write this newsletter. Perhaps now I won’t start movie marathons as soon as it’s dark enough to turn the TV on without dealing with the glare. Maybe I’ll get to read for pleasure again once my NYC class trip is over. Who knows.
In all honesty the next two months are probably just going to be manic marathon reads of the next five Dungeon Crawler Carl books, since hopefully I’ll get all of them from the libary before the new one comes out.
In the meantime though, I wrote an essay about the Tom Waits biography I read for my publishing class last month and now I’m posting it here because it’s basically the same writing I do here but about a Tom Waits bio instead of fiction. I’ve expanded on some bits of it, so it’s not just a copy and paste rehash - no word limits here!
For some context, this was an essay that had a prompt about some of the topics we’d been talking about in class, and I focused on ambition, failure, and community. We got to pick the biography we wanted to read, so of course I had to be difficult and pick a musician instead of a writer (the assignment said “artist” so it was up to interpretation). My mom really liked Tom Waits, though I don’t remember her playing a single album when I was a kid. She had about 2/3rd of his albums on CD and they were on the special CD rack I wasn’t allowed to touch, so I only listened to the albums I could get from the library: Swordfishtrombones, Frank’s Wild Years, Alice, and Mule Variations.
My mom was aggressively possesive of music. No one was allowed to like what she liked, every good band had to be kept a secret. I, on the other hand, cannot shut up about how much I love the new Johnny Blue Skies (aka Sturgill Simpson) album Mutiny After Midnight and telling literally anyone who will listen that the line from “Make America Fuk Again” about having “Hunter Biden energy” and “making a hooker fuck around and fall in love” is just so top tier. My favorite songs are “Stay On That” and “Situation.” I listened to the album 25 times last week when it got “leaked” on youtube. Like legit no joke 25 times. Go buy it it’s amazing I preordered both the CD and the clear vinyl record, even before I knew that this album was going to be masterpiece of dance, joy, and horniness.
Anywho. Back to the matter at hand.
Better Off Without A Wife: Reflections on Tom Waits, Ambition, and Changing Your Mind
Barney Hoskyns’ biography of Tom Waits, Lowside of the Road starts the way that most biographies start, with the story of where the subject came from, their childhood, etc. It’s in these early moments that so often we see the first inklings of a desire for fame and fortune, and while it manifests a little differently for Waits, it’s still from an early age that we see the character begin to emerge. Dressing in such a way that puts him out of step with his peers and carrying a decorative cane, the young Waits seemed to already be putting together what would ultimately define Wait’s career - the portrayal of a character, sometimes to his own detriment, especially in the early 70s through 80s.
He was never performing as himself, very much on purpose, but underlying the facade is still a strong desire to perform. Not necessarily live, though, it turned out that Waits did not enjoy touring, one of the few authentic facets of the cantankerous attitude he often had while on stage. But in the studio, each album finds Waits more often than not inhabiting the characters of his sings, whether one offs, like the older man (much older than Waits’ 23 at time of recording) Tom Frost in “Martha” on Closing Time or the recurring character Frank, likely modeled after his own father, on Swordfishtrombones’ “Franks Wild Years” and the subsequent musical and album of the same name.
Waits also moonlighted as a character actor, appearing in multiple Francis Ford Coppola films including Bram Stoker’s Dracula (1992), Jim Jarmusch’s Down By Law (1986), and other films after the publication of this book. Ultimately, I think that most important facet of Waits’ ambitions were those that had to with storytelling. Performance was certainly an aspect, but where I see Waits at his most evocative and powerful is on the albums where he is functioning as a storyteller. Though he tends to disavow the albums he recorded before meeting his wife Kathleen Brennan, Waits has a through line on those albums that carries from his Asylum records to his Island and ANTI records that centers on storytelling and character building. The biggest distinction from his early albums is Waits’ desire to shed the concept of his persona as a character.
His early persona of a drunkard with an affinity for jazz and projection of imagined poverty proved to be stickier than he would have liked and he has largely spent his time (at least with American audiences) shedding that skin, especially once he moved from Asylum records to Island. But despite that, he still created a discography full of characters that were not just extensions of himself, and I think ultimately that’s the evolutionary realization of the ambitions of character he had shown since he was a child.
Failure is such an odd thing to discuss in this context, because in the US, Tom Waits could easily be considered a commercial failure and just left at that. His 1992 Frito-Lay lawsuit won him 2.6 million dollars, more than all the sales of his records had made up to that point. (Hoskyns, pg. 356) His success as an artist was certainly not without setbacks, but I don’t think any aspect of his career could be considered a failure in the way that I think we might traditionally think of it. The closest his career came to failure was his tour opening from Frank Zappa’s band Mothers of Invention, where fans of Mothers of Invention were decidedly not fans of the jazz stylings of Waits and his touring band. Crowd ranged from bored to actively hostile, and these early touring experiences probably informed Waits’ dislike of touring throughout his career. But ultimately, the tour was not a failure - he still got paid, he wasn’t kicked off the tour, and by all accounts, Frank Zappa was a mentor to Waits and an overall good tour mate.
The failure came not from a lack of success, but rather from just being in the wrong room. The albums Mothers of Invention had released most recently prior to their 1974 tour, Burnt Weeny Sandwich and Weasels Ripped My Flesh (both released in 1970), were closer stylistically to the albums waits would release in the 1990s than to anything Waits was doing at the time of the tour.
Waits still continued to record music, despite having to work a little harder to find his audience, especially with executives often struggling to market him even as a “prestige” artist, with his only real airplay being on college radio. Though it’s not explicitly stated in the text, I don’t think it’s a reach to say that Waits continued writing and recording music because he simply didn’t know what else to do with himself, besides drinking, which even he knew was not going to work out long term, leading to multiple attempts at sobriety, which did eventually stick.
If anything, in the way Waits’ career is framed in this biography, there really wasn’t any great “failure,” which I think is largely the biggest fault of the book. The hero worship of Waits by Hoskyns tends to gloss over some of the more negative aspects of Waits’ history, especially his alcoholism, and also has a vague sense of resentment towards Kathleen Brennan at the same time it acknowledges that her presence is likely one of the biggest factors in Waits’ continuing production of and experimentation with music. Ultimately, it turns out despite his insistence on Nighthawks at the Diner, Waits was likely not better off without a wife, as Brennan would push him to work with Robert Wilson, whom Brennan greatly admired, leading to Black Rider and Alice, both of which began as music for theatrical productions Wilson wrote. Brennan was also likely the biggest factor to Waits success in getting sober for good.
The pursuit of experimentation leads to what I think is the most important part of Tom Waits’ career - The pivot. The ability to leave behind a persona and a style in pursuit of another, to pursue other creative avenues, and work to create authentically. It’s not that Waits’ early work is inauthentic, but rather that it was built on a persona and as Waits evolved and matured he wanted to leave it behind. The true failure would have been for Waits to continue to produce music acting in a way that was more phony than the original persona had been or to quit completely. The pivot is the most important aspect to dedication to craft, in my opinion.
While obviously there are artists and writers who can work in the same medium or genre or style for their entire careers (the Beastie Boys and James Taylor come to mind), for me it’s more important to see the artists who successfully pull off the pivot. Ambition is helpful as a starter, and obviously no career is without failures (no matter how much your biographer wants to pretend otherwise), but in order to have a career that lasts and leaves a legacy, sometimes there has to be a pivot.
The artists and writers I admire the most are almost all people who have done a pivot (or five) or work in various genres – David Bowie, Sarah MacLean, Sturgill Simpson, Norman Jewison. Having read this biography of Tom Waits, I am left considering why this idea of being able to pivot is so important to me. There are other aspects of his history and career that I resonated with, like the way he built his community, or didn’t build, as the case may be, especially when he decided he was going in a new direction and not taking anyone with him, and how important his privacy is to him.
But in terms of creative fulfillment, the way that Waits consistently just did what he wanted for the most part regarding his sound is, if nothing else, an endorsement for flying below the radar of fame. Because he wasn’t making the record label the amounts of money that his label peers were, they were largely hands off on production. As someone who does want to work in more commercially leaning genres, it’s interesting to think about how I plan to function within the constraints of both a publisher’s desires but also the consideration of audiences while still pursuing creative fulfillment. Waits was making more money off lawsuits than his music and paying his bills with royalties from other musicians like The Eagles (“Ol’ 55”) and Rod Stewart (“Downtown Train”).
I know myself fairly well, and one of the character shortfalls I am least likely to work on is how easily I get bored. I pick things up, I’m obsessed, and then I’m over it. On the one hand, that is probability a liability in terms of finishing things and sticking things out, but I’m an optimist and I think it’s a strength in that I’m unlikely to get pigeonholed. I love to try new things, and while I don’t know that I would do a total pivot like Waits did when he no longer wanted to be a drunk jazz man, where I leave everyone and everything behind and burn some bridges and leave some friends in the dust, there’s something comforting about seeing artists able to find success after changing their minds/style/genre.
David Bowie made a career out of pivots and innovations and while Tom Waits can be sorted into two distinct eras - jazz and experimental, there are other forays into acting and being a dad, showing a persistence in his determination to not be tied to being just one thing. But within his various different aspects at the end of the day he is a constant of sorts, the mythology he built around himself all coming together to become Tom Waits, as opposed to David Bowie, who is defined by his chameleonic existence. Though Waits claims that he was done with jazz, it’s influence and the influences of the other music he drew inspiration from on his Asylum records are still present in his later albums. His efforts to preserve his privacy mean that on some level he is appearing as a character anytime he performs, whether conscious or not, though I think it is more conscious than Hoskyns wants to admit in the book.
I also thought a lot about how I value my privacy, and the privacy of my family as I read the book, and how that is at odds with my ambitions for fame and fortune. I really do like the more public facing aspects of being a writer, not as much as the writing itself, obviously, but it feels like one more avenue to achieve my socialite dreams. But with that also comes the weight of deciding how to present myself and how much of myself I want to be on display, and how much access I want readers to have, which is something I think needs to be a consideration early on. As I read about Wait’s early career and how accessible he was in his Tropicana bungalow, and the reputation that he built for himself, there was a sense that later on there was regret that he allowed people so much access to him, similar to the regret he expressed about having built a character that was drunk jazz man, as later on in life it was hard to shake either, even when he did get sober. The privacy thing I think was easier just by nature of living in a time before social media and also never achieving the levels of fame that would lead to paparazzi tracking down your family residence.
I have always intended to publish under a pen name, but I also have written my newsletter for almost three years under my own name, and now have to decide if I want to continue to do that or retcon the whole thing and change every refence to my name to my pen name. Though a much smaller scale issue, I’m facing much the same dilemma as Waits, having allowed people access to information about me that I now think I would rather they did not have.
But ultimately, the most important takeaway for me is the idea that I can always change my mind. Seeing another creative who successfully changes up what they’re doing and pursues creative fulfillment in the way that best suits them at the time is a reminder that I can do the same. It’s hard sometimes to remember that it doesn’t matter how much time or effort I put into something, if I’m not happy I can always change my mind, and those experiences will still serve me. I am not tied to what I wrote as an undergrad (crime fiction), or to the careers I thought I was going to have (I’m actually really glad the homicide detective thing didn’t work out). All that matters in the end is that I’m pursuing what makes me feel creatively fulfilled and lets me write and produce the work that feels authentic to me.
Other Things I Read And watched Recently
Road Trip With A VAmpire, Jenna Levine - have we talked about how much I love road trip stories?
I’ve watched 15 movies since my last ‘here’s what I’m watching’ update, so I think maybe I’ll just do a big movie round up for my next post.


