Come autore "conto terzi", ha scritto canzoni per Gary Allan, Mark Chesnutt, Elvis Costello, The Dixie Chicks, Vince Gill, Patty Loveless, George Strait, Lee Ann Womack, Blake Shelton e altri. Ha collaborato inoltre con Dr. Ralph Stanley, Buddy Miller e Donna the Buffalo.
Discografia parziale 1991 - Planet of Love 1994 - Pretty Close to the Truth 1995 - Every Second Counts 1996 - Persimmons 1998 - Whisper 1999 - I Feel Like Singing Today 1999 - Onward Through It All 2001 - The Other Sessions 2001 - Point of No Return: The Unreleased 1989 Album 2002 - Lost in the Lonesome Pines 2003 - Wait 'Til Spring 2004 - Headed for the Hills 2006 - Bluegrass 2006 - Country Super Hits Vol. 1 2007 - The Bluegrass Diaries 2008 - Honey Songs & the Dream Players 2009 - Could We Get Any Closer? 2010 - Patchwork River 2011 - Reason and Rhyme 2012 - Carolina Moonrise 2012 - Buddy & Jim 2013 - Old Time Angels 2013 - Black Roses 2014 - I'm a Song 2015 - Soul Searching 2016 - This Changes Everything 2017 - London Southern 2018 - Time Flies 2018 - Jim Lauderdale and Roland White 2019 - From Another World
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