Clare Bowditch began writing songs at the age of three, and continued writing them in private until 1998, when she met John Hedigan and, on the same night, formed a band. They called themselves "Red Raku", and recorded two albums along with producer/drummer Marty Brown, who is now Clare's husband. Having performed on the Melbourne pub circuit since she was seventeen years old, first with Quarter Acre Dream and then with Red Raku (they recorded two albums), Bowditch first came to prominence in 2005 with the release of her second album What Was Left, which received excellent critical reviews, and high rotation airplay on national radio stations such as Triple J, although her success can be largely credited to the strong support of local independent radio stations throughout Australia, who championed her early work.
On stage, Bowditch is known best for the beauty of her songs but also for her satirical on-stage humour, her unconventional use of everyday objects (tea-pots, bottles, old Casiotone) for sound-effects, and her ability to tell the truth but tell it slant.
Clare supported Leonard Cohen on his 2010 Australian tour after being handpicked by the Canadian singer-songwriter. Bowditch was joined by fellow Australian musician Deborah Conway, who was the support act for the second show of the Melbourne stop of the tour. Clare revealed in a 2012 interview that she received a marriage proposal from Cohen during the tour, which also involved a shared journey in Cohen's private tour jet—Bowditch turned down the proposal and explained, "I got to spend all that time with him. Most of the time I just sat there watching and smiling and being amazed at the theatre of it all. He was absolutely charming."