In 1998, Redmond encountered vocalist/songwriter Uniit Carruyo at an open-mic night at Collegetown Bagels, in Ithaca. Soon, she was in the band as well, and they began to play out with more frequency. The band recorded their debut album, The Things We Keep, in early 1999, which was subsequently released on the burgeoning I-Town imprint. The album established the band's airy sound, drawing from the worldbeat tradition of Paul Simon and Lucky Dube, a mix of distinctly American pop hooks with African arrangements. The band wasn't always convincing in their attempts at reggae, but managed to parlay it into something more interesting by playing up their strengths: knowing that they couldn't necessarily form a deep pocket, they emphasized the breeziness of the music to great success.
The group's second record, Good Thoughts, was released the following year, and greatly benefited from a higher production value, as well as the contributions of cellist Hank Roberts (another I-Town member) on several cuts. Though the band continued to tour and record at a hectic pace, laying down tracks for a new album, both Sim and Carruyo managed to find time to record and release solo discs -- Redmond contributing with Wishing Well, and Carruyo with Uniit. Soon after, Life Is Water -- the latest from the Sim Redmond Band -- was released. The band followed the release with their first national tour, including several gigs on a self-named I-Town Roadshow, which exposed the groups in many major markets for the first time. ~ Jesse Jarnow, Rovi