Born in 1981, Day started playing piano as a youngster and took hold of a guitar at age 14. By the next year, he had secured his first live appearance at Captain Nick's; two years later, he was touring full-time. Citing Jeff Buckley, Radiohead, and Dave Matthews among his main influences, Day focused heavily on pop-minded acoustic music, and his recognition grew as he opened for the likes of the Wallflowers, Shawn Mullins, Remy Zero, and David Gray. By 2000, Day had amassed enough original material to release an LP, Australia, which he financed himself.
When Stop All the World Now appeared that October, it was a polished, richly produced record that revealed a newfound emphasis on pop/rock music. "Collide" became a Top 40 single, and Day continued to tour in support of the album through 2005. Although a handful of legal battles forced him to take some time off of the road, he still celebrated his live act by issuing the Live From… EP before the year's end.