Jacob Milstein is a tonic concoction of low-res Americana and devout lyricism, of jeweled folk lulls and twisted country enchantments.

Having moved frequently earlier in life, from Oklahoma to New York City to Montana to New Orleans to Nashville, Tennessee, Milstein is a buzzing embodiment of whatever warped affinities and acoustics make up the American songbook.

After dozens of demos and DIY recordings as a folk soloist, Milstein's first full-length album, As Free As Wanting Anything, came out in 2015, introducing audiences to his ornate vibrato, velveteen portraiture, and captivating feel. This was a follow-up to his bedroom split 12" in 2012, Graduation Music, and his 2013 release of the cassette Charm as one half of the Northwestern punk band Oll Breds.

Since this early work, he has written constantly, and honed his storytelling, stage, and improvisational craft. 2019 saw his first release in four years, the single The Old Flames Look So Bright. In 2020 he formed the pandemic-era Nashville indie two-piece Paperboat to home record and release the lush and eclectic album Big Tent in 2021, and throughout 2022 and 2023, he gathered a family of backing musicians to perform 3 hour shows every week, entirely of his original songs, at some of East Nashville's most popular nightlife establishments.

2022 also saw the releases of a single Old Timer, with a double single, Demosahoya, in June, and When the Sun Comes Up and On the Plains, later that year. In 2023, the rate of releases ramped up: in June, he began the project of putting out an unreleased song every week for a year. The series, called Invitation to a Ritual, led not only to a constant stream of songs, but to the writing of series of personal stories in correspondence to his growing mailing list. In 2024, the pace of those song releases relaxed to accomodate the development of the live show Lonelyland, which, with his band and stage crew, Milstein debuted in Nashville in March.