| Year | Winner(s) | Title | Nominees | Ref. |
| 1987 | Al Bunetta, Dan Einstein, Hank Neuberger (producer), various artists | Tribute to Steve Goodman | - John Prine for German Afternoons
- Loudon Wainwright III for I'm Alright
- Nanci Griffith for Last of the True Believers
- Peter, Paul & Mary for No Easy Walk to Freedom
| |
| 1988 | Steve Goodman | Unfinished Business | - Joan Baez for Asimbonanga
- John Hartford for Annual Waltz
- Loudon Wainwright III for More Love Songs
- Washington Squares for The Washington Squares
| |
| 1989 | Tracy Chapman | Tracy Chapman | - John Prine for John Prine Live
- Michelle Shocked for Short Sharp Shocked
- Sweet Honey in the Rock for "Emergency"
- Clive Risko, Various Artists for Homeland - A Collection of Black South African Music
| |
| 1990 | Indigo Girls | Indigo Girls | - Gipsy Kings for "Bamboleo"
- BeauSoleil for Bayou Cadillac
- Tracy Chapman for Crossroads
- Guy Clark for Old Friends
| |
| 1991 | Shawn Colvin | Steady On | - Suzanne Vega for Days of Open Hand
- Indigo Girls for "Hammer and a Nail"
- Maura O'Connell for Helpless Heart
| |
| 1992 | John Prine | The Missing Years | - Indigo Girls for Live - Back On the Bus Y'all
- BeauSoleil for Cajun Conja
- Rosanne Cash for Interiors
- Jerry Garcia, David Grisman for Jerry Garcia & David Grisman
| |
| 1993 | The Chieftains | Another Country | - Joan Baez for Play Me Backwards
- T-Bone Burnett for The Criminal Under My Own Hat
- Indigo Girls for Rites of Passage
- Michelle Shocked for Arkansas Traveler
| |
| 1994 | Nanci Griffith | Other Voices, Other Rooms | - BeauSoleil for La Danse de la Vie
- Shawn Colvin for Fat City
- Bob Dylan for Good As I Been to You
- Jimmie Dale Gilmore for Spinning Around the Sun
- Janis Ian for Breaking Silence
| |
| 1995 | Johnny Cash | American Recordings | - Shawn Colvin for Cover Girl
- Iris DeMent for My Life
- Nanci Griffith for Flyer
- Indigo Girls for Swamp Ophelia
| |
| 1996 | Emmylou Harris | Wrecking Ball | - The Chieftains for The Long Black Veil
- Bob Dylan for MTV Unplugged
- Steve Earle for Train a Comin'
- John Prine for Lost Dogs and Mixed Blessings
| |
| 1997 | Bruce Springsteen | The Ghost of Tom Joad | - Jerry Douglas, Peter Rowan for Yonder
- Jimmie Dale Gilmore for Braver New World
- Richard Thompson for You? Me? Us?
- Gillian Welch for Revival
| |
| 1998 | Bob Dylan | Time Out of Mind | - Guy Clark for Keepers - A Live Recording
- Iris DeMent for The Way I Should
- Indigo Girls for Shaming of the Sun
- John Prine for Live on Tour
| |
| 1999 | Lucinda Williams | Car Wheels on a Gravel Road | - Billy Bragg, Wilco for Mermaid Avenue
- Steve Earle for El Corazon
- Emmylou Harris for Spyboy
- Lyle Lovett for Step Inside This House
| |
| 2000 | Tom Waits | Mule Variations | - BeauSoleil for Cajunization
- Ani DiFranco, Utah Phillips for Fellow Workers
- John Prine for In Spite of Ourselves
- Linda Ronstadt, Emmylou Harris for Western Wall - The Tucson Sessions
| |
| 2001 | Emmylou Harris | Red Dirt Girl | - Billy Bragg, Wilco for Mermaid Avenue Vol. II
- Johnny Cash for American III: Solitary Man
- Steve Earle for Transcendental Blues
- John Hiatt for Crossing Muddy Waters
| |
| 2002 | Bob Dylan | Love and Theft | - Buddy and Julie Miller for Buddy & Julie Miller
- Various Artists for Poet: A Tribute to Townes van Zandt
- Gillian Welch for Time (The Revelator)
- Lucinda Williams for Essence
| |
| 2003 | Nickel Creek | This Side | - Johnny Cash for American IV: The Man Comes Around
- The Chieftains for Down the Old Plank Road: The Nashville Sessions
- Steve Earle for Jerusalem
- Patty Griffin for 1000 Kisses
| |
| 2004 | Warren Zevon | The Wind | - Rosanne Cash for Rules of Travel
- Emmylou Harris for Stumble into Grace
- Tom Paxton for Looking for the Moon
- Lucinda Williams for World Without Tears
| |
| 2005 | Steve Earle | The Revolution Starts... Now | - Ani DiFranco for Educated Guess
- Eliza Gilkyson for Land of Milk and Honey
- Patty Griffin for Impossible Dream
- John Carter Cash, Various Artists for The Unbroken Circle - The Musical Heritage of the Carter Family
| |
| 2006 | John Prine | Fair & Square | - Ry Cooder for Chávez Ravine
- Rodney Crowell for The Outsider
- Nickel Creek for Why Should the Fire Die?
- Bruce Springsteen for Devils & Dust
| |
| 2007 | Bob Dylan | Modern Times | - Jackson Browne for Solo Acoustic, Vol. 1
- Rosanne Cash for Black Cadillac
- Guy Clark for Workbench Songs
- Mark Knopfler, Emmylou Harris for All the Roadrunning
| |
| 2008 | Steve Earle | Washington Square Serenade | - Mary Chapin Carpenter for The Calling
- Ry Cooder for My Name Is Buddy
- Patty Griffin for Children Running Through
- Tom Waits for Orphans
| |
| 2009 | Robert Plant, Alison Krauss | Raising Sand | - Joan Baez for Day After Tomorrow
- Ry Cooder for I, Flathead
- Rodney Crowell for Sex & Gasoline
- Emmylou Harris for All I Intended to Be
| |
| 2010 | Steve Earle | Townes | - Neko Case for Middle Cyclone
- Tracy Chapman for Our Bright Future
- Shawn Colvin for Live
- Elvis Costello for Secret, Profane & Sugarcane
| |
| 2011 | Ray LaMontagne, The Pariah Dogs | God Willin' and the Creek Don't Rise | - Jackson Browne, David Lindley for Love Is Strange: En Vivo Con Tino
- Mary Chapin Carpenter for The Age of Miracles
- Guy Clark for Somedays the Song Writes You
- Richard Thompson for Dream Attic
| |