[4] He attended West Chester University,[5] where he graduated with a degree in psychology, and also played in cover bands including Hot Spoon Gilly.

[2][6] His major label debut album Black Hole Rainbow was released on January 10, 2020, on Capitol Records.

[10] On October 22, 2020, Gilfillian released a track-by-track cover of Marvin Gaye's 1971 album What's Going On[11] with 100% of the profits donated to Tennessee's Equity Alliance Fund.

Produced by Jeremy Lutito (Joy Oladokun, NEEDTOBREATHE), the album includes the single “All I Really Wanna Do” which peaked at No.

Gilfillian performed at Newport Folk Festival and Montreal Jazz Fest,[15] and at the 2018 NFL draft in Dallas.