Photo: Kyle Craighead Haynam

JACKSON, Wyo. — Dry wit with a raw honesty, lyrical quirkiness, and an evocative voice that brings to mind Fiona Apple’s deeper cuts, Abby Webster lives in a Wilson cabin and writes songs on piano, guitar and ukulele. Though she’s been relatively quiet as a stage performer since moving to the valley two and half years ago from San Francisco, she’s a prolific songwriter that’s aiming to change that. In July, she was one of two artists in the state to be awarded a Performing Arts Music Fellowship from the National Endowment of the Arts and the Wyoming Arts Council, “a merit-based honor of excellence in an artist’s field” that was accompanied by a $3,000 award.

“I’ve never applied for anything like that before,” Webster said. “I’ve never won anything and that was really moving to me. I cried when I found out. It was helpful, too, because I used the money to buy some gear that I needed. It’s so hard paying for that stuff out-of-pocket.”

The fellowship “excellence” refers to Webster’s growing discography, which includes the most recent five-song cup of tea, cup of joe EP (Sept. 2020), singles “Sick” (April 2020) and “Tall Boy” (2017), Reverie EP (2017), Put a Box to Your Ear; Listen to the Ocean (2016), and Drunk & Pretty (2010). Aside from solo ventures, Webster has an electronic duo with long time collaborator Trey George called Ski Lift, which has also been releasing music for about a decade. Offerings include the recent two-song single “But We Love Each Other” (Aug. 2020), “I Want You More Than Myself” (2019), How Seriously You Take Yourself EP (2018), and the debut Romantic EP (2011).

Lyrics from “Sick”: Well I’m felling sick, so I can’t sing for very long.
                                   Need ginger and honey; I am the ant trapped in your honey.
                                   All I do is think of you in the soft blue rain
                                   blurring the window you look through all day,
                                   afraid to leave the prison you’ve made,
                                   skippin’ town in an alcohol haze,
                                   keeping all your promises vague,
                                   now you don’t have anything to say.

Though cup of tea, cup of joe was softly released to BandCamp just a couple of months ago, it’s not likely to stay online long. The handful of tracks will be remixed and coupled with “Sick” and another batch of songs that will culminate into a full-length release in early 2021, Polyphony. The release process is also fluid regarding how and when it will be released.

“I hate the songs and just not proud of them but the reason is because I waited too long,” admitted Webster. “My friend Julia started managing me and I’m talking to this label out of Oakland so I still need to do some thinking on that. I’m not sure if it will be released under the label yet, but the date will be January 15.”

Webster’s first life memory was a light-up toy keyboard at a neighbor’s house when she was about three years old. The programmed sounds caught her ear. And though the philosophy major followed music obsessively while growing up, she was more devoted to being a dancer until the passion for writing poems and stories led her to write her first song at age seventeen. That ushered the recording of her debut album Drunk & Pretty when she was nineteen, coupled with a dive into the instrumental side of composition.

“I learned to play instruments so far as I needed to support my writing,” Webster said. “That first album was my introduction to piano. I took a break for a while after.”

She would re-tap that musical spirit in college as a background singer and eventually as lead singer for Jessie James Wax Museum. She also taught herself to play organ. At the time, she looked to indie folk songwriters as inspiration.

“Writing-wise, I loved the confessional style of Bright Eyes/Connor Oberst and Joanna Newsome. That pushed me to want to make music. What struck me about that music was how it made me feel, and that’s what I became attached to. There was something deeper about it.”

During Webster’s pop-up outdoor concert at the Center for the Arts back in September, she told stories behind many of the songs, including a stomp-country tune that stands out from the vibe of the rest of her repertoire. After referring to an ex-boyfriend that was on the short side, the signature chorus line got a chuckle from the crowd: “I ain’t got no boy but I got my tall boy / don’t need no small man when I got my tall can.”

As a seasoned studio musician, Webster enjoys the creative control that it offers. Connecting that to the live show is a different challenge.

“I hate playing live, well, I shouldn’t say that…I love it. It’s taken me a lot of time to get there. I don’t like to be the center of attention but I’ve worked on it. People’s reactions to me when I’ve played live have been strong for the most part. It really gives me room for expressiveness that I don’t have when I record. I’ve had people come up to me and cry [after hearing a song], and that’s really powerful and amazing but also makes me feel uncomfortable. Jackson audiences have been less emotional.”

“When I record, I like having more control over my voice to manipulate and sound differently. Like Ski Lift, that’s a different voice. My new record, that’s a different voice than I’ve had in my previous releases. I think one of the strong points of my music is the raw and emotive aspects and that can be tough [to capture] in the studio.”

Jackson’s music scene has long been a head-scratcher for specific types of musicians that don’t fit into the box required to perform on local stages. Metal, hip-hop, punk, avant-garde—there currently aren’t stages for those genres. Even for an acoustic singer-songwriter it can be tough when original music is the focus, though it hasn’t been without encouragement from other locals.

“The Jackson scene is a lot more welcoming than other places for me. Musicians were excited for me to be here. That’s really refreshing. There’s less pretension in it. I haven’t performed that much here because I don’t think my music is that conducive to a resort town since I don’t cover other people’s songs. For the most part, I write avant-garde pop songs. It’s funny, musicians I’ve talked to here are admittedly grateful for the work of playing weddings, and they play into a system. I want to start a folk band and would enjoy performing more, moving in the direction of my song ‘Tall Boy.’”

To keep up with Webster’s releases, visit or follow her at

Buckrail @ Aaron

Aaron Davis is a songwriter, multi-instrumentalist, vocalist, and producer-engineer at Three Hearted Recording Studio, covering the Teton County music scene as a journalist-photographer since 2005.