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Rainey studied at the New England Conservatory of Music with free jazz saxophonist Joe Maneri. Rainey's music during his early- to mid-twenties was, like Maneri's, characterized by long microtonal lines. Rainey's first CD, Ink, featuring Dan DeChellis, was released in 1997. After a controversial 1998 solo concert in Washington D. C. attracted a considerable amount of attention to Rainey's music, he and trumpeter Greg Kelley formed Nmperign with the goal of avoiding linear approaches to form and melodic contour. Nmperign, including Rainey, Kelley and Tatsuya Nakatani, recorded its first CD in 1998.
Since 1998, Rainey has recorded extensively, including a number of projects with nmperign (minus Nakatani) and collaborations with musicians and composers like Jason Lescalleet, Le Quan Ninh, Ralf Wehowsky, etc. He continues to pursue a more sound-based (as opposed to note-based) approach in his work with nmperign, whereas his solo work, while far from traditional, often involves the use of more melodic lines. Since 2000, he has also led the bsc, a large ensemble that uses both acoustic instruments and electronics.
Beginning in 2005, Rainey has released a handful of works based around electronics and field recordings, notably his 2006 collaboration with Ralf Wehowsky, I don't think I can see you tonight, and his solo EP, Two Bites of a Bitter Sweet.
Rainey also occasionally appears as a sideman in more traditional settings, most recently in recurring work with ex-Galaxie 500 indie rock duo Damon & Naomi, for whom he has also done horn and string arrangements.