Having started as a drummer, Pilley started songwriting in 1989. Together with guitar-player Ross Edmond, Al Denholm (Bass) and Iain Bruce (Drums), he founded Hobotalk in the late 1990s. In 1998, Hobotalk signed to Hut Records. Debut-EP Pictures of Romance was released in November 1999. Both the EP and the following Scotland-Tour (supporting the indie-rock-band Gomez (band)) received positive critical response for their heartfelt sound rooted in American-style folk.
Hobotalk's debut album Beauty in Madness was released in 2000 and also widely received with critical acclaim being shortlisted for the Mercury Prize. Despite all this, the album had only little sales and was hardly noticed by a wider public.
In 2002, the band split from Hut Records. It was not until 2005 that a second album was released. Notes on Sunset appeared on Circular Records (UK) and Glitterhouse Records (Europe).Again, the album gained positive reviews, but did not form a commercial breakthrough for the band.
The bands line up by now was Pilley, Ali Petrie (keys) ,Klive Smith (guitar), Allan Cranston (drums), Nick Houldsworth (guitar,mandolin).
In 2007, Hobotalk's the album Homesick for Nowhere was released.
"Alone again or" saw Hobotalks final album release in 2008.
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