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Season 2 continues with a very special guest — singer, songwriter, and actor Rainsford (Rainey Qualley)!

In this episode, Will dives deep into Rainey’s world of atmospheric indie pop and her journey from acting in shows like Mad Men and films like Ocean’s 8 to releasing heartfelt songs like Horse and her latest single Butterfly. They talk about how becoming a new mother has reshaped her outlook on life, the meaning behind her upcoming debut album Before Blue, and why writing about happiness is harder than writing heartbreak.

Of course, it wouldn’t be The Encore Club without some chaos — Rainey builds her dream concert in a crumbling seaside castle filled with animals, choosing Cocteau Twins, Dolly Parton, and the legendary Prince as her lineup. Expect fun games like Play, Repeat, Delete and Mashup Apocalypse, unexpected stories from her career, and a few laughs along the way. This episode is equal parts heartfelt and entertaining, giving fans a closer look at one of indie pop’s most intriguing voices.