Described as "a psych-funk oddball...a contrarian", Mockasin played a role in the contemporary crossover of psychedelia with indie music, and has been praised for his unique approach to songwriting.

[6] Mockasin has also worked with Lawrence Arabia, Liam Finn, Dev Hynes, Mick Fleetwood, and MGMT, as well as his own father on the 2021 album It's Just Wind released through American label Mexican Summer.

[7] Those who have cited him as an influence include Beach House, Tyler, the Creator, Nilüfer Yanya, James Blake and Charlotte Gainsbourg.

[8][6] Mockasin was born in Napier in 1983, and raised in the "dinky wee settlement" of Te Awanga in Hawke's Bay, to father Ade Hosford, a musician formerly of Autumn Stone and Philharmonia Orange.

In 2003, after moving back to Wellington, Mockasin briefly played in a band called "The Hornery Stiffmen" (later to become a track title on "Please Turn Me into The Snat"),[12] consisting of Blake Pryor (bass) (who later appeared as an actor in "Bostyn 'n Dobsyn") and Christopher Chalmers (drums), before forming his principal New Zealand group "Connan and the Mockasins", named after Connan's interest in making his own shoes.

[13] Playing alongside Connan were Ross Walker (upright acoustic bass) and Seamus Ebbs (drums).

The first release to bear the name "Connan Mockasin" was the 2010 LP, "Please Turn Me into The Snat", which was re-released as "Forever Dolphin Love" the following year.

[14][15] This album saw a significant change in style to Connan's previous work, and has been described by critics as "fluid", "meandering and blissful", "seemingly effortless" and "mesmerising".

[18] It was at this stage Hosford put together an incarnation of the existing Connan Mockasin live band: Matthew Eccles (drums), Nicholas Harsant (bass), Sam Dust (keyboards) and Rory McCarthy (percussion).

[20] Connan Mockasin toured with Radiohead in Australia and New Zealand throughout November 2012, playing sold-out shows in Auckland, Brisbane, Sydney and Melbourne.

Jassbusters will accompany a five-part film written and directed by Connan called "Bostyn 'n Dobsyn", which took an alleged 20 years to develop, and reached its current form after a 10-day shoot in Los Angeles in July 2016.

The first episode "Belly Bubble" was premiered at the Vista Theatre, Los Angeles before a concert by Jassbusters, followed by a Connan Mockasin performance.

Recorded at Gary's Electric Studio in Brooklyn, Mockasin, along with Jassbusters' real-life counterparts (Nicholas Harsant on bass, Matthew Eccles on drums, and Rory McCarthy (AKA infinite bisous) on rhythm guitar), freestyled across long live takes, weaving under, over, and straight through each other's blurry riffs."

Mockasin's music is known for its unconventional subject matter, themes, styles and instrumentation; he has been positively labelled as openly "weird", and a pioneer of "trippy, mutated soul".

Those who have cited him as an influence include Beach House, Tyler, the Creator, Nilüfer Yanya, James Blake and Charlotte Gainsbourg, the latter two he has since collaborated with.

[35] Connan briefly curated concerts under the title "Mockasin's Wet Dream", the first of which took place in London's Moth Club,[36] in collaboration with Charnwood based online music-library Tasty Morsels.

The second Wet Dream would take place at Texan festival Marfa Myths, organised by American label Mexican Summer, and would include appearances by Ariel Pink and Andrew Van Wyngarden.