Cliff Westfall

Baby You Win

New album, Baby You Win, out July 13.

New York-based, Kentucky-bred songwriter Cliff Westfall can make you laugh out loud or cry in your beer – sometimes in the same song. Whether delivering an uptempo country shuffle or a sentimental weeper, he dives headlong into tales of heartache, loss and addiction, transforming them into hook-laden gems with a mixture of cleverness and bravado. Indeed, for Westfall, that transformation is central to what country music is all about.


New York-based country songwriter Cliff Westfall writes songs about heartache, loss, addiction… you know, funny songs. Or he can turn on a dime and dive headlong into a sentimental weeper.

The Kentucky native delivers with a mixture of wit and bravado that, for Westfall, is central to what country music is all about. On his new album, Baby You Win, to be released July 13, 2018, he’s assembled a crew of some of New York’s best musicians to explore a new idea of Americana, drawing inspiration from sources often forgotten by the current country scene. 

“I feel like the humor of people like Roger Miller, Don Gibson, and Del Reeves is neglected nowadays,” Westfall says. “A lot of current country music makes you want to ask, ‘Hey, does anybody remember laughter?’ And you know, it’s not really anything against what anyone else is doing, it’s just that the ability to laugh at your troubles seems to have gotten lost.”

The songs on Baby You Win are bitingly acerbic, dependent on the twisty puns, bittersweet humor, and turns of phrase that used to define country music.  

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"more and more" premieres on popmatters

PopMatters is premiering my song “More and More” today. It’s a pretty sweet review, and really an honor to be featured there. As some of you know, this song was a finalist at the MerleFest songwriting competition this year, and it’s the first track we’re releasing into the wild, so please stay tuned for further news. And after you check it out, feel free to pre-order my album [release date July 13, 2018] here.

Check out the premiere here!

"More and More" finalist in MerleFest Chris Austin Songwriting Competition

"More and More," a track from my upcoming album Baby You Win is a finalist in the Chris Austin Songwriting Competition that's held at the legendary MerleFest in North Carolina later this month. I'm honored it was selected and thrilled to perform the song in front of a panel of judges that includes Rodney Crowell and Johnny Williams.

Learn more about the songwriting contest here and listen to the track below!