Chris Castig Co-founder of Adjunct Prof at Columbia University Business School.

The Sound of Songwriting: with Keller Williams

7 min read

“I’m a music lover first, musician second, and songwriter third”, Keller Williams admits. He pauses for a moment continues, “Yeah, that statement says it pretty clean and clear, I’m in it for the love of music, and for love of performing the music I love, and songwriting that’s next.”

With each bar of music Williams has written, you can feel his sincerity and gratitude for having the opportunity to live his dream as a professional musician. “Starting out, the object was to play music and make a living no matter what, and once I started to do that I started to really appreciate that”, he tells me. Later explaining that his inclination to play solo shows serendipitously came from the fact that earlier in his career it was more cost effective “rather than splitting $150 four ways”. Now almost twenty years later, Wiliams has led a prolific: including 16 albums, a variety of side-projects, and the musical curiosity to navigate unfamiliar genres (distant from his bluegrass roots) such as like techno and children’s music.

In regard to songwriting he tells me, “I’m lucky for the ability to come up with these songs that some people like, but at the same time it’s more about performing.” Indeed, Williams is probably best known for his live shows. At a Keller Williams show he almost always performs solo, playing half a dozen instruments one after another and looping these sounds, all of which consummate in a wonderfully orchestrated live rendition of the original album recording.

A common thread throughout all of Williams’ music is his desire to write songs that not only entertain his audience, but can simultaneously amuse himself: a song like “Bob Rules” hilariously imagines what it might feel like to be a contestant on The Price Is Right. And then there’s “Doobie in My Pocket” – a song about boarding a plane with the realization that you may have left marijuana in your suitcase (along with the paranoid assumption that the TSA are onto you!). “You’ve got to pay attention, or you’ll miss the punch line”, Williams warns his audience prior to performing “Doobie in My Pocket” live for the first time.

At a crowded mid-town diner in New York City, Williams and I spent a long lunch discussing his inspiration for writing songs, as well as the stories behind some of his fan’s favorite song such as “Kidney in a Cooler” and the enigmatic “Multisylabic”.

When I inquired about the meaning of some of the words in “Multisylabic”, Williams veers from his train of thought and begins recounting the lyrics to me from across the table, “Multisyllabic, Sans-linguistic pro-fantastic, Slyly systematic…”. Before diving into the story, Williams pauses to sip his coffee and starts chuckling, “Remember what I said in the beginning about songwriting? So… I’m probably a lyricist fourth.”

What is your process for writing a song?

A lot of my songwriting stems from the chorus. I start with a chorus and then once I have the chorus the verses fall into place. And then if I get lucky, a bridge falls into place.

Do you write at certain times?

Before I had kids, I’d spent three or four weeks on tour and come back with 2 weeks off. And the first week I’d just get used to being off the road and decompressing, and then the second week is when the boredom kicks in, it’s like a kid. You get used to the routine of being on the road.

So that second week, that’s when the bulk of my creative juices start flowing. But after I started to have kids there was less and less boredom time. All the time was being focused on them, and then when they would go to sleep I’d have my creative time. Or sometimes I’d get up at 5:30 and 6 in the morning.

Where does inspiration come from?

Sometimes songwriting stems from conversation with really interesting intelligent people that I have in my life, and I might stop and say, “Hey can I have that? Can I use that?” hopefully they say yes – sometimes they say OK but you’ve got to cut me in on it. So maybe I’ll give “executive producer” credit.

Is there a song you’re thinking of in particular?

My friend Cam, he was on the management team, and we gave our selves the writing assignment of trying to come up with super intricate words, that are really smart intelligent words, that are not in my personal vocabulary, but yet trying to create a song with it, and not necessarily have it mean something. What we came up with a song called “Multisyllabic” [Dream].

Do you find yourself gravitating toward a writing formula?

We’ll it’s almost impossible to write something that hasn’t been written before, although we all strive for that, we strive to write something that lasts longer than we do. And that’s kind of my ultimate goal too.

I can’t really deny the formula I came with as far, chorus, verse, chorus, jam section bridge, verse, chorus. It’s hard to stray away from something like that.

What I have noticed is that the older I get, I give myself more writing assignments, which push me creatively.

What do you mean by “writing assignments”?

I give myself writing assignments, for example: ‘write a bluegrass science fiction song.’ I’ve never tried to do that before, it’s not something that totally hasn’t been done before, but it’s something I’ve never done before.

Can you give examples of songs where you may have strayed from writing such positive songs?

Once I tried to step aside from all this good that is happening to me try to focus on something that is a different emotion – so I wrote about an ear infection. And that was real-time writing – during the ear infection. It’s a real physical kind of pain. That song was written in the 4th hour after taking my painkillers [when all the pain comes back].

I’ve never gone political, but I came up with this one song kind to poke fun at Rush Limbaugh – I guess there was a time when he was on the news saying “I Hope You Fail” talking directly at Obama, so I took his words and spun them around, and wrote a song with his words about him, with the focus being on free speech, and how Rush is the alpha male of free speech and able to say almost anything he wants and the country thrives on that and gets off on it.

And so whether you agree with him or not, it’s here to stay because he’s totally allowed to do that. And this song was kind of the same thing, taking his mentality, not necessarily his right wing political views, but just free speech in general and using my right of free speech to make fun of Rush Limbaugh. So that’s kind of my songwriting,

I wonder about “Odd”. I wonder if it has to do with this new writing regiment you talked about, because I feel like the songs at this period in your life are become more serious, and less comedic.

Which in a way, is odd.

Exactly, is that why you named the album “Odd”?

Yeah if you listen to my music I go from these happy go lyrics that I usually have, and then you hear this and it’s definitely odd, that’s kind of where the concept came from. We tossed around words like “Wack”. Like, ‘This whole record is “Wack!”

“Odd” works much better than “Wack”

Yeah I agree. Also I think the album artwork kind of scares people, it’s a very Meatloaf 80’s metal type of imagery. Which is what I was going for: the Fabio, black light Spencer’s Gifts thing. I was going for funny – the only way I can have abs and big monster pecks is to draw them in.

Much of your live show is solo with instruments looping, so when you’re writing songs I wonder if you’re playing with loops at the beginning of the writing process?

No, writing is just on a guitar, or in a notebook. The looping is pretty much spontaneous, and on stage.

The albums are definitely studio, we’re actually in the studio playing the instruments, playing to a click track. After the guitar track, put in a bass line, play it all the way through, there’s no looping when we do it live, I like to use humans.

Who is the first person you share a new song with?

My wife, Emily.

She’s your producer?

I definitely value her opinion, and there’s some stuff that I know that she won’t like and I might not show her those, because I know that I like it, and so whenever I write something new, whether it’s ready or not, I’m going to play it at the next show. I’m so excited to have new material that I definitely don’t wait around until it’s perfected. And she definitely has a problem with that. She wants me to work on stuff – sometimes I won’t have the words fully memorized. But my way of thinking is that it’s my song, it’s my way of thinking is that it’s my song… it’s the first time I’m playing it, I can make up words as I go along too. [laughs]

But I value her opinion. I usually run everything by her, and she gives me writing assignments too. I have a fun times twisting those writing assignments around and having fun with that.

And she knows when there hasn’t been a song written for a while!

She takes some of the stuff that I say too, she’ll point out little sayings that I say and stop me. She might say, “Oh that would make a great kids song”

When I posted on Facebook that I’d be interviewing you about songwriting today, I received an overwhelming number of replies from your fans. So, I’d like to ask you about a two songs in particular that kept coming up.

My fans are the best. Sure.

“PORTAPOTTY”. Did you ever fall in love with the girl in the Porta-potty line?

I think in general there’s been a lot of Porta-potty sightings, I did Grateful Dead shows, and Phish shows from 1987 until around ‘95. At the time I was in my early twenties and going to a lot of shows, making as much money as I can to buy a bunch of tickets and going out for 2 weeks with The Dead.

In the late 80s, up until 1990, they were letting people camp in the parking lots at Grateful Dead shows. They would do like 3 nights in one venue and then a day off, and in that day off people would leave that parking lot and go to the next parking lot where the next show was. And you could stay there for three days. And of course it turned into this whole village. Going into the show was the last thing on some people’s minds. So this is where I was when I wrote Port-a-potty.

You’re curious if it’s true? It wasn’t one particular girl, but a type of girl that you see.

Kidney in the Cooler, is it true?

100% true. On the way down to Deep Ellum, a section of Dallas, we broke down in Perry, Oklahoma and we got towed.

That line about “Little America”? That came when we were driving through Wyoming: on these big billboards we kept reading: “Little America! 100 miles! Hot Dogs! Swimming Pools!”, and then “80 miles!”, “20 miles!”

So you eventually made it to “Little America”, and what was it?

Little America was this giant oasis of a truck stop in the middle of the Wyoming wide open. Giant multi-acre hotels, showers, and a 24 hour auto-repair garage. And that’s what got us! We had a leaking radiator at the time and thought, “ok we’ll just go get this fixed we’ve got a day or two to kill.” And that took a whole 28 hours, which put us off schedule a day.

So we’re driving south, and two days later we break down in Oklahoma. They couldn’t work on our car because there was a woman delivering a kidney who’s car had broke down as well. She had this kidney in a Playmate cooler and was on her way to Oklahoma City. So they all had to work on her car first. We stayed in that town for three days!

Kidney in a cooler? You can’t make that stuff up.

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Chris Castig Co-founder of Adjunct Prof at Columbia University Business School.