Why Vilray Plays a Cheap Old Gibson: Limitations, Subway Woodshedding, and Writing Songs From 1947

The Musician Who Quit for Ten Years

Vilray writes songs that sound like they fell out of a 1947 songbook. He performs them in duo with Rachel Price of Lake Street Dive, the two of them huddled around a single ribbon microphone, and the whole thing feels so complete and so historically fluent that it is easy to assume he has been doing it since birth.

He has not. In his early twenties, after writing intentionally absurd songs with the friends who would go on to form Lake Street Dive, Vilray stopped. Not a slow fade. A full stop. He took a job above a factory in Queens, did accounting, moved into customer service, eventually ran the customer service department, and did not write, sing, perform, or play guitar for roughly seven years.

What is striking is that he does not describe those years as wasted. He describes them as necessary.

"When I entered it, I was pretty self-conscious about my output. I would write songs and I would say this sucks for this reason or that reason. It made songwriting extremely unfun."

If you have ever put the guitar down because your own internal critic got louder than your curiosity, that is a familiar feeling. The interesting part is what pulled him back.

A Broken Pinky and the Subway Woodshed

Vilray broke his pinky. Suddenly, not playing was no longer a choice he was making, it was a condition imposed on him. That flipped something psychologically. Not playing because you might get back to it someday is comfortable. Not playing because your hand is in a cast makes the mortality of the whole enterprise very obvious.

A friend who ran a free jazz series in a Williamsburg basement booked him for a show six months out. Vilray protested that he had nothing to play. The friend told him to start thinking about it.

So Vilray went underground. Literally. He started busking in the subway to get back into fighting form, playing standards and near-standards that he half remembered by ear, working them out in skeletal, imperfect versions.

Why the Subway Is a Perfect Practice Room

This is one of the most useful ideas in the whole conversation, and it is worth unpacking for anyone trying to rebuild chops or prepare material for a gig.

• Audience turnover creates infinite repetition. A crowd forms, a train comes, the crowd leaves, a new crowd forms. You can play the same tune ten times in a row and every performance is a first performance for someone. Mistakes are absorbed by the churn.
• Real stakes without real consequences. There are actual human beings listening, so your nervous system treats it as a performance. But nobody is reviewing you, and nobody is coming back tomorrow.
• Immediate correction. As Vilray put it, you finish a tune, realize you got one chord wrong, and fix it on the next pass while it is still fresh.

Most of us do not have a subway platform, but the principle transfers. Find a low-stakes context with a real listener and a repeat loop: an open mic where you play the same tune three weeks running, a farmers market, a nursing home, a video camera you actually publish to. Repetition plus mild social pressure is the fastest chops-recovery protocol there is.

Playing under the street also taught him something about the music itself. Old love songs, played face to face with people who were between work and home, or falling in love, or getting broken up with, genuinely landed. That gave him the confidence to start slipping his own originals into the set to see if anyone would notice they were not standards. Nobody did.

Then Rachel Price came to one of his early shows and said, essentially, let us make music together.

The Guitar: A Gibson ES-125 and the Case for Limitation

Vilray plays a mid-sixties Gibson ES-125, a P90-loaded archtop that was Gibson's affordable workhorse for decades. It is not a fancy guitar. That is the point.

Why the P90

The P90 is a single coil pickup with a wide, flat coil, and it sat at the center of the sound of jazz guitar from the mid-fifties through the mid-sixties. Vilray's take is simple: P90s have a personality that got sanded off when humbuckers arrived. Humbuckers were quieter and more stable, but some of the character went with the noise. If your ear is drawn to that midrange bark with a little air on top, the P90 is the pickup that made those records.

Why the Lack of Sustain Is a Feature

Here is the detail most players miss. On many ES-125 style guitars, the bridge is anchored directly into the top rather than floating freely, so the top barely vibrates. The result is a hollow guitar that behaves almost like a solid body with a very fast decay. Notes fall off quickly and there is very little bloom.

"It can be frustrating in a kind of way, but it is also like, oh wow, that is part of it."

Listen to Wes Montgomery or Grant Green with that in mind and a lot of phrasing choices make sense. They could not lean on a note and let it ring through a ballad. They had to keep moving inside a dotted quarter. The instrument's shortcoming became a rhythmic aesthetic.

Practical takeaway: before you fight your gear, ask what your gear is telling you to play. A guitar with short decay pushes you toward continuous eighth note lines, chord melody with reattacks, and rhythmic density. A guitar with enormous sustain invites space and long held notes. Neither is better. Matching your vocabulary to your instrument is a shortcut to sounding intentional.

Technology Writes the Music

Vilray extends this idea into a broader theory, and it is one of the best segments of the interview: nearly every revolution in music has a technological precursor.

• The ribbon microphone created crooning. Before ribbons, singers used harsh, high-end-heavy microphones that required volume to register. So you stood in front of a big band and belted like a trumpet, which is why Rudy Vallee sounds the way he does. The ribbon mic arrives, and suddenly Bing Crosby is possible. Intimacy became recordable.
• Wartime and Depression-era budget guitars were built with whatever materials were available, and their cheap, boxy voices became iconic tones rather than compromises.
• The flamenco guitar is essentially a lightly built classical with less sustain, and that fast decay is exactly what allows rapid-fire lines to speak without notes smearing into each other. The technique grew out of the instrument.

The lesson for players: what sounds like an aesthetic inevitability is usually circumstance. That is liberating. You are allowed to build your sound around whatever you actually own.

Writing Songs for Ghosts

Ask Vilray how he crafts songs that pass as lost standards and his answer is disarmingly concrete. He picks a singer and writes for them.

"This is going to be a song for Peggy Lee. This is for Frank. This is for Ella Fitzgerald. This is for Fats Waller. Those people have different tastes, and obviously it is all transmuted through my conception of them, so there is no truth to it. That is what makes it authentic and not stale."

The distinction he draws matters. Copying a specific song feels dead, like someone trying to get as close as legally possible to a tune they love. Writing toward an imagined artist is different. You are filtering a style through your own faulty, personal impression of a person, and the gap between the real Nat King Cole and your version of him is where your originality lives.

His song "Hate Is the Basis of Love" started exactly this way. A wedding commission client mentioned that she and her partner loved the same things but, more importantly, hated the same things. Vilray heard the phrase "hate is the basis of love" as a Nat King Cole shout chorus, complete with the early-forties trick of a second voice singing in unison, an effect the King Cole Trio used before double tracking existed.

Try This Exercise

Pick an artist you love from a specific era. Write a tune they would have chosen to record. Not a tune that sounds like a song they did record, but one they would have picked from a stack of demos. That constraint forces you to think about a whole sensibility: phrasing, range, humor, harmonic taste, subject matter. It is one of the most efficient songwriting prompts available.

Commissions as a Songwriting Engine

Vilray writes commissioned songs for weddings and anniversaries, and he treats them as real work rather than favors. His method is worth stealing: he asks the client to send everything, the longer the better, and specifically asks them not to tell him what the song should be.

"I do not want to write your song," he says. "Just tell me everything, and then I will find the thing."

This gives him raw material with no imposed structure, which is exactly what a writer needs. It also produces songs that outlive their occasion. "Do Friends Fall in Love," one of the duo's best known tunes, was his first commission, written for a couple to walk down the aisle to.

He is also honest about failure. Sometimes it does not come, and he refunds people. Not because their story was boring, but because he was not in the right place. Writing on demand is not a factory process, even for someone very good at it.

The Study Habit Underneath All of It

Two things built Vilray's fluency, and neither is a scale exercise.

Obsessive chronological listening. At LaGuardia High School in New York, he was required to take jazz courses to keep playing guitar. He fell in headfirst, bought a giant album guide, and followed sidemen like hyperlinks. Blue Train led to Lee Morgan, which led to Art Blakey, which led to Wayne Shorter, which led to Herbie Hancock. By graduation he had worked more or less chronologically from 1936 to 1976.

Transcribing arrangements, not just solos. Currently he is learning Sinatra Capitol Records material arranged by Nelson Riddle and Gordon Jenkins, adapting string and horn writing to guitar. He cannot play a whole arrangement, and that is fine. He grabs little horn parts to weave between chord changes.

The insight he pulled from it is one guitarists chronically neglect: where you play something changes what it means. In "In the Wee Small Hours," a melodic idea is stated, then restated later by strings from a different register. Same notes, different color. On guitar you have the same option built into the fretboard, and most players never use it.

Practical takeaway: take one eight-bar melody and play it in four different positions on the neck. Same pitches, different string sets. Notice how the low, thick version and the airy high version tell different emotional stories. Then start using that as a compositional device rather than an accident of fingering.

What to Take Away

• Time away from the instrument is not necessarily lost time. Vilray came back without the self-consciousness that had made writing miserable.
• Build a low-stakes performance loop. Repetition in front of real humans beats repetition in your bedroom.
• Stop fighting your guitar's limitations. Short sustain, a quirky pickup, a boxy tone: these are prompts, not problems.
• Study arrangers, not only guitarists. Horn and string writing will teach you voicing and register in ways guitar tab never will.
• Write for a specific imagined artist. The imperfection of your impression is the source of your voice.
• Follow sidemen through discographies. It is still the best way to build deep historical fluency.

Vilray's whole career is an argument that constraint is generative. A cheap guitar with no sustain, a subway platform with no green room, a decade with no music at all. Each of those looked like a limitation, and each one shaped the sound.