Man, no matter how many times you hear this one, it hits hard…

Brad Paisley and Allison Krauss teamed up for the now iconic “Whiskey Lullaby” back in 2003 on Brad’s Mud On The Tires album. While it peaked at Number 3 on the Country Charts, it went on to win the CMA Song of the Year award and is now 2x Certified Platinum by RIAA.

And to this day, it’s commonly regarded as one of the saddest country songs of all time.

No shortage of artists have put their spin on it over the years, most recently with Cleto Cordero of Flatland Cavalry teaming up with his wife Kaitlin Butts on her Sad Yeehaw Sessions EPbut there will always just be something special about having Brad on the track.

Perhaps it’s the difference between this song and some of his more questionable others

Regardless, Brad played the Opry back on September 16th of last year and brought out old reliable, teaming up with Caylee Hammack for the duet.

Caylee has linked up with a few artists recently for some great collaborations, like Ashley McBryde’s “Brenda Put Your Bra On,” Chris Stapleton on “Small Town Hypocrite”, and the legend Alan Jackson a few years ago with the Don Williams song “Lord, I Hope This Day Is Good”.

Safe to say, the two blew it out of the park, and no matter how many times you’ve heard the song, it’s always worth another listen.


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