Careless Love, first released in 2004, is a rich collection of cover versions with tunes from Bob Dylan to James P Johnson, and included Peyroux's milestone rendition of Leonard Cohen's Dance Me to the End of Love. For the sole original on the album, producer Klein and Jesse Harris co-wrote Madeleine's signature tune and many fans' favourite, Don't Wait Too Long.

With sales of half a million copies, the album shifted Peyroux from the exclusive Jazz realm into the mainstream arena, and it remains her most popular release. This deluxe edition includes a full previously-unreleased 2005 live set, recorded by Basque Public Radio for the Festival de Jazz de Vitoria-Gasteiz in Spain. Madeleine performs the repertoire from Careless Love, plus additional bonus songs.