Webley plays the guitar and accordion, sometimes providing percussion by stomping or shaking a plastic vodka bottle filled with coins.

He has also organized several commemorative concerts and events memorializing everything from tragedies in his hometown of Everett, Washington, to tomatoes.

[5] His sound has been compared to Tom Waits,[6] Vladimir Vysotsky,[7] Leonard Cohen,[6] and Bob Dylan.

Webley organized the Monsters of Accordion tour, an all-accordion extravaganza that took place on the West Coast.

[13] The tour came together when Webley was invited to play at an accordion shop in Oakland, and met two Bay Area accordionists, Daniel Ari and Aaron Seeman.

[14] The tour has since featured such accordionists as Corn Mo, Geoff Berner, Amy Denio, Mark Growden, (former Gogol Bordello member) Stevhen Iancu, and Eric Stern (frontman of Vagabond Opera).

It was performed live at the historic Everett Theater one day before the centennial (hence the title, One Hundred Years Ago Tomorrow).

The troupe put on free performances across 5 states, attracting crowds hundreds or even thousands to waterfront parks, marinas, and boat ramps.

[25][26][27][28][29] Webley has announced that there will be a series of 11 collaborative projects between him and his songwriter friends, and each recording will be limited to 1,111 numbered copies.

Webley repeated this tradition the following two nights, first after a concert at Bard College, where he and a group of students collaborated on a song called "Clown Car to Mulberry", then at Sarah Lawrence College, where Webley and almost the entire audience performed the hardcore punk-inspired "Bad Milk".

At a concert at The Saint in Asbury Park, New Jersey, in January 2009, Webley was joined on stage by Calamity Menagerie to perform "Ways To Love" and "Quite Contrary" – a song he rarely plays at live shows.

In December 2011, Webley announced the intention to make his back catalogue available as paid downloads online on the website BandCamp.

In February 2018, Webley announced the release of the new Amanda Palmer music video "Judy Blume" which he directed.