Although Annie and the Oakies is a relatively recent name in the southern Wisconsin bluegrass scene, its roots run much deeper. All the members of A&TO were part of the Oak Street Ramblers, a Madison favorite for nearly two decades. In 2022, the band rebranded and released its eponymous debut album. Although Annie and the Oakies has a foundation based on classic bluegrass stylings, its repertoire divulges a wider range of influences. Indeed, the unexpected cover song reworked to fit a bluegrass lineup has become a staple of the band’s live performances.

The band consists of Annie Emmenegger on guitar and vocals, Ian Alderman on mandolin, dobro, and vocals, Jeff Kunkle on bass, Mark Schlutt on banjo and vocals, and Tina Thompson on fiddle. When not playing together, all of the members are involved in side projects that allow them to explore the diversity of their musical DNA. Annie frequently performs solo gigs in the area. Mark and Ian are founding members of the up-and-coming bluegrass act Sorry Mountain. Tina, an accomplished classical performer, leads the Yahara String Quartet. Jeff plays electric bass in the regionally popular Cajun Strangers and the synth-rock band The Moonboot.

Since its inception, the band has played several high-profile shows, including the Stoughton Opera House, LarryFest, multiple Madison festivals, and a sold-out album release show at the North Street Cabaret. They have a monthly residency at the Harmony Bar and Grill in Madison, performing every second Wednesday of the month. And, most importantly, every Thursday night is band practice in Jeff’s basement, as has been the case for over twenty years.