“Orphan Annie” was written by Norman Blake. It is on his first solo album, Home in Sulphur Springs (Rounder, 1972), recorded on 30 December 1971 at Glaser Sound Studios in Nashville with Blake on guitar and mandolin and Tut Taylor on Dobro.
The song is sung by a traveler who has been on the road too long. He has been riding planes and hailing cabs in search of sunshine he keeps missing, and he is sitting in New York City, wishing he were in Nashville around Fifth and Broadway, where the Cumberland runs and home is not far away. He asks Annie whether her Nashville nights are still warm, whether a storm is coming up west of town, and whether the rivers are dark and muddy where the willows grow, and he counts nine more days until he is home off the road.
Tony Rice sang and played it on his 1983 Sugar Hill album Church Street Blues, recorded at 1750 Arch Studios in Berkeley, California, and the Tony Rice Unit’s live album Live at the Birchmere (Acoustic Disc, 2022) includes it. The Punch Brothers recorded it in November 2020 at Blackbird Studios in Nashville for Hell on Church Street (Nonesuch, 2022), with Chris Thile singing lead, Chris Eldridge and Gabe Witcher on harmony, Noam Pikelny on banjo and Paul Kowert on bass. The Darrell Webb Band included it on Lover’s Leap (Mountain Fever, 2017).