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So Long So Wrong, another Union Station album, was released in 1997 and won the Grammy Award for Best Bluegrass Album.One critic said its sound was "rather untraditional" and "likely [to] change quite a few ...minds about bluegrass." and was included on the Buffy soundtrack in 1999.
She also collaborated on a project with the Cox Family in 1994, a bluegrass album called I Know Who Holds Tomorrow.
Later that year, she signed to Rounder Records, and in 1987, at 16, she released her debut album Too Late to Cry with Union Station as her backup band.
The album includes the traditional tunes "Wild Bill Jones" and "Beaumont Rag", along with a bluegrass interpretation of The Allman Brothers' "Midnight Rider".
From the age of 12 she performed with bassist and songwriter John Pennell in a band called "Silver Rail", replacing their previous fiddler Andrea Zonn.
and wrote some of her early work including the popular "Every Time You Say Goodbye".
She was invited to join the band with which she still performs, Alison Krauss and Union Station (AKUS), and later released her first album with them as a group in 1989.