With a soulful, smoky vocal delivery that works in tandem with her intimate, noir-shaded songs, Ashley Shadow is the project of Vancouver musician Ashley Webber. She contributed to recordings by the likes of Bonnie "Prince" Billy and the Cave Singers before making her solo debut with 2016's Ashley Shadow. The former's Will Oldham returned the favor by appearing on her second album, Only the End, in 2021.

Long before adopting the Shadow moniker, Webber played bass in post-punk band the Organ. Formed in 2001, they released a series of EPs and one full-length, 2004's Grab That Gun, before Webber left the group in 2005. Over the next decade, she collaborated with an assortment of well-regarded artists, including singing for the Pink Mountaintops (2006's Axis of Evol and 2009's Outside Love), Bonnie "Prince" Billy (2008's Lie Down in the Light), and the Cave Singers (2009's Welcome Joy). Webber signed with Felte Records for her eponymous Ashley Shadow debut. Produced by Joshua Wells of Black Mountain and Lightning Dust (the latter his duo with Ashley's sister Amber Webber), it was released in April 2016.

The songwriter reconnected with Wells to record her second album, Only the End, which arrived on Felte in September 2021. It featured a duet with Bonnie "Prince" Billy ("Don't Slow Me Down").

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