After a short stint with the group Black Bear and a European vacation, Diane returned to the States and began work on her next album, which saw the light of day as The Pirate's Gospel in 2004. It caught the attention of small label Holocene Music, which reissued the album in 2006 with new artwork and a revised track listing.

The Pirate's Gospel was critically well received, and over the next year and a half, Alela Diane's star was on the ascent. A 10" vinyl five-song EP, Songs Whistled Through White Teeth, was released in the U.K. in 2006, and Diane toured extensively in both the United States and the British Isles during the following year. In 2008, she toured Europe once again and found time to record an album with Headless Heroes, a side project whose debut album, The Silence of Love, was a collection of cover songs. Her next solo LP, To Be Still, marked her debut for Rough Trade in 2009. Although it was universally well-received by critics, Diane ditched the album's hushed, intimate appeal in favor of a beefier sound, which was unveiled on 2011's Alela Diane & Wild Divine. Toward the end of her marriage to Wild Divine's guitarist Tom Bevitori, Diane began writing songs that would ultimately comprise 2013's About Farewell, a stark, honest portrayal of their break-up. ~ Chris True