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US singer-songwriter Ryan Adams has described Galway-based Crowley as among "the best songwriters no-ones heard of'. Despite such commendation, the slightly sombre singer-songwriter tellingly recorded his third and fourth albums in his sister's former and current houses (respectively) rather than anywhere more extravagant or palatial. Prior to this, Crowley had sought (and obtained) an Arts Council grant to fund flights to the USA to record his second album, 2001's When You Are Here You Are Family, with producer Steve Albini. The ensuing album, which drew its name from a line of New York graffiti that Crowley had inadvertently photographed, was recorded in just five days. A sense of low key seems apposite for Crowley: his music is brooding, sorrowful and understated, inviting comparison with Smog, Red House Painters, Low and James Yorkston.

Since releasing 2004's A Northern Country, Crowley has increasingly become aligned with Fence, the music-making collective that includes Yorkston, King Cresote and the Pictish Trail among its numbers: he featured on their Don't Fudge With The Fence compilation. Crowley also contributed a cover of "West Palm Beach" to the Will Oldham tribute album I Am A Cold Rock, I Am Dull Grass. He has notably opened for, and found kindred spirits in, artists including José González, Howe Gelb and Badly Drawn Boy.