Connan originally started a "blues-pop" band whilst living in Wellington, New Zealand, ...
as Connan and the Mockasins. The group consisted of Connan Hosford (vocals, guitar), Ross Walker (upright acoustic bass) and Seamus Ebbs (drums).
In April–May 2006, the band released their second EP, Uuu It's Teasy, and toured New Zealand to promote the album. They played a fundraising New Zealand show in Wellington on 26 May 2006, before relocating to London on the 30th.
After a series of concerts in London, the band visited New Zealand again for a national 2006/2007 Summer tour.
In 2007, the band moved from London to a village in East Sussex south of England. Ross Walker was replaced by James Milne, of Lawrence Arabia and Reduction Agents fame, on bass guitar. The band then played the CMJ festival in New York. Towards the end of 2007 Ebbs left the band to pursue his career, shortly before Hosford returned to New Zealand for a national tour in 2008 with a new lineup - becoming a solo act under the name 'Connan Mockasin'.
In 2008, Connan collaborated with Norman Cook (Fatboy Slim) on a song for the upcoming Brighton Port Authority album. He also finished a tour with Pete & The Pirates and set out on a February tour with Late of the Pier. Connan has also collaborated with musicians Liam Finn and Lawrence Arabia. Finn also contributed to their last album. In 2009, Connan Mockasin started touring with befriended band The Veils through Europe, as well as gigs with Liam Finn and Micachu & the Shapes.
In August 2009, Liam Finn performed with a new band called BARB on a small New Zealand tour consisting of Connan Hosford, Lawrence Arabia (James Milne), Eliza Jane Barnes, Seamus Ebbs, Jol Mulholland and Wild Bill Rickets. Their album (recorded at Roundhead Studios in Auckland, New Zealand) is set for release in August 2010.
Connan plays a reshaped Stratocaster, similar in looks to a Vox Teardrop.
In 2010 Connan embarked on a UK tour with Crowded House, playing huge theatre-like venues with mostly seated areas. This proved an interesting challenge for Connan and his group as most would consider his music much more alternative or left-field than that of Crowded House, although Connan had expressed an interest in playing to seated crowds in places such as libraries or theatres.
Connan supported Mystery Jets at their gig on 8 July at Somerset House in London with a line up consisting of Elroy Finn (brother of Liam Finn) on drums, Wild Bill Rickets on percussion and Nick Harsant on bass. That summer the line up (with occasional guests on guitar and keys) played several festival shows such as Latitude Festival and Offset Festival.
In 2010 Connan supported Warpaint on some of their UK tour dates.