The Best Song From Every GRAMMY-Award Winning Best Country Album

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In 1965 and 1966, Roger Miller took home the GRAMMY Award for Best Country & Western Album. After that, the category was discontinued until 1995 when it received its current denomination of Best Country Album. At this point, a number of these albums have become legendary in their own right, but we have to ask– what’s the best song on each of these albums? Let’s dissect.

The Best Songs From Every GRAMMY-Award Winning Best Country Album:

1995. Stones in The Road // Mary Chapin Carpenter // “Shut Up and Kiss Me”

1996. The Woman in Me // Shania Twain // “You Win My Love”

On an album that produced four No.1 songs, it’s hard to pick a favorite. But, “You Win My Love” is the choice.

1997. The Road to Ensenada // Lyle Lovett // “Don’t Touch My Hat”

1998. Unchained // Johnny Cash // “Unchained”

1999. Wide Open Spaces // The Dixie Chicks // “You Were Mine”

Safe to say– this album defined a generation. It produced three No. 1 singles and two other Top 10 hits, but musically– “You Were Mine” is the best.

2000. Fly // The Dixie Chicks // “Let Him Fly”

2001. Breathe // Faith Hill // “The Way You Love Me”

“Breathe” won the GRAMMY for Best Country Song, but “The Way You Love Me” is the one you could listen to on repeat.

2002. Timeless: Hank Williams Tribute // Various Artists // “I Can’t Get You Off Of My Mind”

2003. Home // Dixie Chicks // “Travelin’ Soldier”

Actually, this one has two– you just can’t ignore “Top of the World.”

2004. Livin’, Lovin’, Losin’: Songs of the Louvin Brothers // Various // “How’s The World Treating You”


2005. Van Lear Rose // Loretta Lynn // “Portland, Oregon”

Jack White produced and played on this album. He thought of it as an experiment and it ended in greatness.

2006. Lonely Runs Both Ways // Alison Krauss and Union Station // “Restless”

2007. Taking the Long Way // Dixie Chicks //  “Not Ready to Make Nice”

They may have been “kicked out” of country music, but “Not Ready to Make Nice” was a statement and still resonates today.

2008. These Days // Vince Gill // All

This is an album of 43 songs and features every name in country music. You pick.

2009. Troubador // George Strait // “Troubador”

2010. Fearless // Taylor Swift // “White Horse”

2011. Need You Now // Lady Antebellum // “American Honey”

This coming of age ballad is more fun to listen to than “Need You Now,” though that one musically deserved every accolade it received.

2012. Own The Night // Lady Antbellum // “We Owned the Night”

2013. Uncaged // Zac Brown Band // “Sweet Annie”

2014. Same Trailer, Different Park // Kacey Musgraves // “Keep It To Yourself”

Kacey Musgraves is a lyrical genius and she gets no better than “Keep It To Yourself.”

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