Kasey Chambers is a country-folk iconoclast who isn’t afraid of vulnerability—the 2002 Australian chart-topper “Not Pretty Enough” was refreshingly frank about personal insecurities tied to narrow beauty standards—and challenging herself sonically. Born in 1976, the Mount Gambier native grew up idolizing Emmylou Harris and initially started playing professionally in a country-folk band with her parents and younger brother in the mid-’80s. By the time she was a teenager, Chambers fronted the quartet, which became known as The Dead Ringer Band and released four well-regarded albums before splitting up in the late ’90s. Chambers made her solo debut in 1999 with The Captain, which spawned the beloved, aching twang-pop title track, before breaking out in 2001 with Barricades and Brickwalls. That album became her best-selling and first No. 1 solo album in Australia—and it freed her up to explore country music’s other avenues, including sinewy Americana (“Pony”), fragile acoustic rock (a cover of Crowded House’s “Better Be Home Soon”), and traditional folk (the spare “Rattlin’ Bones,” with then-husband Shane Nicholson). Chambers has continued to push herself to explore new vistas as her career has progressed, leading to empowered songs such as 2017’s “Ain’t No Little Girl,” a torchy blues-rock number that asserts personal authority and self-confidence.