| 1990 | Ben's Song | | | | | | | |
| 1990 | I'll Accept the Rose | | | | Chanson | | | |
| 1990 | Lady | | | | | | | |
| 1990 | Let Me Drown | | | | | | | |
| 1990 winner | Don't Turn Your Back | | | | | | | |
| 1991 | Rave On | | | | | | | |
| 1991 | So Listen | | | | | | | |
| 1991 | Weather Out the Storm | | | | | | | |
| 1991 (Holly Cole) | Girl Talk | | | | Chanson | | | |
| 1991 winner | Home I'll Be | | | | Chanson | | | |
| 1992 | Days and Days | | | | | | | |
| 1992 | I Never Met a Liar (I Didn't Like) | | | | | | | |
| 1992 | Man of Steel | | | | | | | |
| 1992 | The Path of Thorns (Terms) | | | | | | | |
| 1992 winner | Orangedale Whistle | | | | | | | |
| 1993 | Fare Thee Well Love | | | | Chanson | | | |
| 1993 | Memory Waltz | | | | | | | |
| 1993 | Underwhelmed | | | | | | | |
| 1993 winner | In My Father's House | | | | | | | |
| 1994 | Just Another Boy (Who Wanted to Fly) | | | | | | | |
| 1994 | Rise Again | | | | Chanson | | | |
| 1994 | Stone and Sand and Sea and Sky | | | | Chanson | | | |
| 1994 | We Can Do Anything | | | | | | | |
| 1994 winner | Man of a Thousand Songs | | | | | | | |
| 1995 | Angels | | | | | | | |
| 1995 | Borders and Time | | | | Chanson | | | |
| 1995 | North Country | | | | Chanson | | | |
| 1995 | Reel 'n' Roll | | | | | | | |
| 1995 winner | Which Way Does the River Run | | | | | | | |
| 1996 | Curious | | | | | | | |
| 1996 | Long Night | | | | | | | |
| 1996 | Shade of Your Love | | | | | | | |
| 1996 | You Feel the Same Way Too | | | | | | | |
| 1996 winner | Peter's Dream | | | | | | | |
| 1997 | A List of Things | | | | | | | |
| 1997 | Don't Take Me Home | | | | | | | |
| 1997 | Fast as I Can | | | | | | | |
| 1997 | Jerk | | | | | | | |
| 1997 winner | Sleepy Maggie | | | | | | | |
| 1998 | Building a Mystery | | | | Chanson | | | |
| 1998 | Everything You've Done Wrong | | | | Chanson | | | |
| 1998 | Fiddle & Bow | | | | | | | |
| 1998 | It's a Personal Thing | | | | Chanson | | | |
| 1998 winner | When I'm Up | | | | Chanson | | | |
| 1999 | Adam's Rib | | | | | | | |
| 1999 | Maybe You're Right | | | | | | | |
| 1999 | Rootbeer & Licorice | | | | | | | |
| 1999 | The Band's Still Playing | | | | | | | |
| 1999 winner | Falling | | | | | | | |
| 2000 | Consequence Free | | | | | | | |
| 2000 | In My Hands | | | | | | | |
| 2000 co-winner | 12 Years Old | | | | | | | |
| 2000 co-winner | Sorry | | | | | | | |
| 2001 | Everything Shines | | | | | | | |
| 2001 | Get Me Through December | | | | | | | |
| 2001 | Make It Go Away | | | | | | | |
| 2001 (Julian Austin) | Take the Money and Run | | | | Chanson | | | |
| 2001 winner | Tattooed | | | | | | | |
| 2002 | Invisible Science | | | | | | | |
| 2002 | It's Not About You | | | | Chanson | | | |
| 2002 | Live | | | | | | | |
| 2002 | Livin' a Lie | | | | | | | |
| 2002 winner | Followed Her Around | | | | | | | |
| 2003 | I'd Never Walk Away | | | | Chanson | | | |
| 2003 | Midnight Angel | | | | | | | |
| 2003 | Sea of No Cares | | | | Chanson | | | |
| 2003 | The Other Man | | | | | | | |
| 2003 winner | Here | | | | | | | |
| 2004 | Another California Song | | | | | | | |
| 2004 | City of Lakes | | | | | | | |
| 2004 | Morning Bound Train | | | | | | | |
| 2004 | The Rest of My Life | | | | | | | |
| 2004 winner | King for a Day | | | | | | | |
| 2005 | Butterfly | | | | | | | |
| 2005 | Happy Baby | | | | | | | |
| 2005 | Not Ready to Go | | | | | | | |
| 2005 | When I Am King | | | | | | | |
| 2005 winner | Sunburn | | | | | | | |
| 2006 | All Used Up | | | | | | | |
| 2006 | Cocaine Cowgirl | | | | | | | |
| 2006 | So She's Leaving | | | | | | | |
| 2006 | Sweet Symphony | | | | | | | |
| 2006 winner | Blackbird | | | | | | | |
| 2007 | Don't Hold Me Down | | | | | | | |
| 2007 | Marching Machine | | | | | | | |
| 2007 | Poor Ol' Broken Hearted Me | | | | | | | |
| 2007 | Run | | | | | | | |
| 2007 winner | Nowhere With You | | | | | | | |
| 2008 | All About U | | | | | | | |
| 2008 | Caught Up to You | | | | | | | |
| 2008 | Lake of Fire | | | | | | | |
| 2008 | Weighty Ghost | | | | | | | |
| 2008 winner | Fashionable People | | | | | | | |
| 2009 | Afflicted | | | | | | | |
| 2009 | Face of the Earth | | | | | | | |
| 2009 | Make You Move | | | | | | | |
| 2009 | Tall Trees | | | | | | | |
| 2009 winner | We Are Young and So Is the Night | | | | | | | |
| 2010 | Anybody Listening | | | | | | | |
| 2010 | Atlas | | | | | | | |
