Born and raised in Seattle, O'Connor was always a bit out of sync with his teenage peers. Understandably so, since he was winning fiddle contests and had mapped out a sketchy career path. O'Connor moved to Nashville in 1983, already a former sideman for jazz violinist Stephane Grappelli, a job that allowed him to play the stage at Carnegie Hall. At the time O'Connor arrived in Music City (the post-Urban Cowboy era), fiddle was hardly in vogue, and it took a couple of years for him to make his mark. Finally, in 1985 the Nitty Gritty Dirt Band used him in their single "High Horse"; thanks to that work, O'Connor's phone number became a popular one with country record producers. Over the next five years he played on 450 albums, including such stellar projects as Trio by Dolly Parton, Linda Ronstadt, and Emmylou Harris; Always & Forever by Randy Travis; Killin' Time by Clint Black; and Loving Proof by Ricky Van Shelton. Despite his success, O'Connor gave up session work to concentrate on his own solo career, increasingly rooted in the classical realm thanks to collaborators including Yo-Yo Ma, Wynton Marsalis, and Edgar Meyer.