Singer and songwriter Dar Williams became a major figure in the contemporary folk music community in the 1990s with her warmly observational songs which are often leavened with gentle wit and pithy wisdom. Williams’ music is tuneful and makes room for upbeat pop influences as well as more somber acoustic sounds, and deals with topical and feminist themes in a manner that’s human and grounded rather than didactic. 1997’s End of the Summer was Williams’ first creative breakthrough after some promising early efforts, 2005’s My Better Self was an album that blended streamlined contemporary pop sounds with personal lyrics, and 2021’s I’ll Meet You Here was a mature and introspective collection about facing life’s uncertainties.

A lot of artists defy categorization. Some do so because they are tirelessly searching for the place they fit, while others are constantly chasing trends. Some, though, are genuinely exploring and expressing their myriad influences. Amy Ray belongs in the latter group. Pulling from every direction — Patty Griffin to Patti Smith, Big Star to Bon Iver — Ray’s music might best be described as folk-rock, though even that would be a tough sell, depending on the song. Ray’s musical beginnings trace back to her high school days in Atlanta, Georgia, when she and Emily Saliers formed the duo that would become the Indigo Girls. Their story started in 1981 with a basement tape called “Tuesday’s Children” and went on to include a deal with Epic Records in 1988, a Grammy in 1990, and nearly 20 albums over more than 35 years. Rooted in shared passions for harmony and justice, the Indigo Girls have forged a career that combines artistry and activism to push against every boundary and box anyone tries to put them in. As activists, they have supported as many great causes as they can, from LGBTQ+ rights to voter registration, going so far as to co-found a Native environmental justice organization, Honor the Earth, with Winona LaDuke in 1993. As artists, they have dipped their toes into a similar multitude of waters — folk, rock, country, pop, and more — but the resulting releases are always pure Indigo.