Jason Darling grew up near Woodstock, NY, and began playing guitar at a young age. After bouncing through a next-generation Deadhead phase, Darling ended up in Greenwich Village, retracing Bob Dylan's footsteps, digging on slide guitar and folk-blues, and scraping by with handyman work at local recording studios. Casual collaborations with pal Leona Naess started paying the bills when she signed with MCA. Darling contributed guitar to 2000's Comatised and participated in the resulting world tour. In between dates he signed with L.A. indie Surprise Truck, wrote and recorded his debut album, and issued it in early 2001. Underground was a literate yet rootsy affair that showcased Darling's expressive slide guitar work. In October 2003, he returned with Night Like My Head (Yep Roc). The effort featured broader arrangements that were filled out with keys and drum programming, and drew comparisons to the work of Shawn Mullins and Jeb Loy Nichols. Darling supported the album with numerous dates, mostly on the East Coast.

Acoustic guitar-driven rock, very much influenced by Neil Young. Jason Darling acknowledges as much with the first song, placing Young dead center in the piece. But the real link is the poetic way Darling expresses himself. The lyrics (and the guitar work, occasionally) don't always follow an obvious linear track. The stuff can get a bit expressionistic at times. The only way to make that work is for the poetry to resolve itself. In other words, the shit had better be good. And Darling is. He slings his songs with an easy intensity, the kind of delivery that's impossible to teach. He is his songs. Kinda cool when that sorta thing works out. There aren't many people who can pull off an ambitious set of songs like this. Hell, most wouldn't even try.. Darling succeeds in spectacular fashion.”

— Reviews - Jason Darling - Aiding and Abetting