McKeown's 2005 album, "We Will Become Like Birds" (produced by Tucker Martine), served as a departure from her earlier work, with a more rock-oriented sound. At a September 1, 2008, concert at The Gravity Lounge in Charlottesville, Virginia, McKeown told the audience that she wrote this album "in an attempt to write myself out of the worst heartache I'd experienced up to that point." Her next studio release, "Sing You Sinners", was released in Europe on the 23 October 2006 and in the United States on January 9, 2007 by Nettwerk. It consists mostly of covers of jazz standards from the 1920s through 1950s.