Born and raised in Bray, Regan came to prominence with the release of his debut studio album, The End of History in 2006.

Mojo magazine gave the album four stars in a review that dubbed the disc "a debut that oozes rare confidence, startling maturity and originality".

[citation needed] The album received a slew of 4 and 5 star reviews from publications including The Times and The Guardian.

[4] Around this time, Regan was photographed by Annie Leibovitz for Vanity Fair magazine's prestigious music portfolio.

[9] Regan released the album to critical acclaim on 8 February 2010,[10] achieving several four-star reviews from several publications, including Mojo, Uncut, Q, Hot Press, Financial Times, The Daily Telegraph, The Guardian and The Independent.

[12] The following year in August, Regan released his third studio album, 100 Acres of Sycamore, with the track "Dogwood Blossom" featuring prominently in Shane Meadows' TV drama This Is England '88.

[13] On 17 August 2012, Hot Press announced that Regan had completed his fourth studio album, The Bunkhouse Vol.

[14] In April 2017, Regan released his fifth studio album The Meetings of the Waters via independent label Abbey Records under his imprint 'Tsuneni Ai'.

To support the lead single, also titled "The Meetings of the Waters", Regan released a music video starring actor Cillian Murphy.

His single "Be Good or Be Gone" has been used in the television dramas Grey's Anatomy, Nearly Famous, and Skins and "Dogwood Blossom" featured in hit series' This Is England '88 and Normal People.