1988 Trio - Dolly Parton / Emmylou Harris / Linda Ronstadt
1989 Hank Williams Jr./ Hank Williams Sr.; There's A Tear In My Beer
1990 Lorrie Morgan / Keith Whitley; 'Til A Tear Becomes A Rose
1991 Mark O'Connor & The New Nashville Cats (featuring Vince Gill, Ricky Skaggs and Steve Wariner)
1992 Marty Stuart / Travis Tritt Honky Tonkin' Is What I Do Best
1993 George Jones with Vince Gill, Mark Chesnutt, Garth Brooks, Travis Tritt, Joe Diffle, Alan Jackson, Pam Tillis, T. Graham Brown, Patty Loveless, Clint Black; I Don't Need Your Rockin' Chair
1994 Reba McEntire with Linda Davis; Does He Love You
1995 Shenandoah with Alison Krauss Somewhere in the Vicinity of the Heart
1996 Dolly Parton with special guest Vince Gill; I Will Always Love You
1997 Tim McGraw with Faith Hill; It's Your Love
1998 Patty Loveless (with special guest George Jones); You Don't Seem To Miss Me
1999 Vince Gill with Patty Loveless; My Kind Of Woman/My Kind Of Man
2000 George Strait with Alan Jackson; Murder on Music Row
2001 Brad Paisley with featured vocals by George Jones, Bill Anderson and Buck Owens; Too Country
2002 Willie Nelson with Lee Ann Womack; Mendocino County Line
2003 Alan Jackson and Jimmy Buffett; It's Five O'Clock Somewhere
2004 Brad Paisley with Alison Krauss; Whiskey Lullaby
2005 George Strait with Lee Ann Womack; Good Times, Bad Times
2006 Brad Paisley with Dolly Parton; When I Get Where I'm Going
2007 Tracy Lawrence with Kenny Chesney & Tim McGraw; Find Out Who Your Friends Are
2008 Alison Krauss with Robert Plant; Gone, Gone, Gone