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.

about cliff westfall

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, 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. Westfall’s a true son of Kentucky and an honest student of the genre, but refuses to be constrained by its definitions. He cites Chuck Berry as his favorite lyricist, arguing that some of Berry’s songs were much closer to their country cousins than lines of race and genre might have suggested. This is Americana outside the box, made by an artist gleefully rifling through the dusty record bins of American roots music and converting them into something new. 

To record Baby You Win, Cliff Westfall enlisted producer Bryce Goggin (Pavement, the Ramones, Antony and the Johnsons, Evan Dando, Phish, Akron Family) and renowned New York guitarist Graham Norwood. The three drew from their extensive connections to assemble a band with a massive list of credits on the scene, like electric guitarist Scott Metzger (Shooter Jennings, Phil Lesh, Joe Russo’s Almost Dead), pedal steel player Dan Iead (Norah Jones, Valerie June), bassist Jeremy Chatzky (Ronnie Spector, Bruce Springsteen, Laura Cantrell), drummer David Christian (Danger Mouse, Mary Timony’s Helium), even the keyboardist from Bruce Springsteen’s E Street Band - Charlie Giordano. The album was cut and mixed over just nine days at Goggin’s studio. “A lot of it was pretty organic,” Westfall says. “That’s how Bryce works and I was lucky enough to have a band good enough to make that work.”

The songs on Baby You Win draw from Westfall’s abiding love of great songwriting. He has an obsessive passion about the smallest details of his favorite songs and albums and he’s lived a life chasing those obsessions. He used to sneak into a friend’s family diner in the wee hours of the morning, after the Owensboro bars had closed, to eat biscuits and gravy and listen to the jukebox’s only two Dwight Yoakam 45s over and over again. Westfall’s love for Yoakam translates to opening song “It Hurt Her to Hurt Me.” His interest in Jerry Lee Lewis’ late 60s Mercury Sessions can be heard in “Till the Right One Comes Along.” A bit of Bob Dylan pops up in “I’ll Play the Fool” and the 70s harmony haze of Laurel Canyon comes around in “The Man I Used to Be.” 

Cliff Westfall was born and raised in Owensboro, not far from tiny Rosine, Kentucky where Bill Monroe invented bluegrass music, and he grew up listening endlessly to Kentuckians like The Everly Brothers who changed the path of popular music. Though he got his start playing cowpunk music in Kentucky, he soon left his home state behind for the bright lights of New York City. “The term ‘country music’ is almost a misnomer anyway,” argues Westfall. “A big part of the original audience was people a generation or two removed from the farm who had migrated to the city. People more familiar with factory work and honky tonks than with the back end of a mule, you know? The music they wanted to hear was as much about cutting loose, dancing and having a good time as it was about sadness and hardship. That was kind of the story of my family. Or maybe I’m just attracted to neon lights, I don’t know.”

That is to say, country music was born in cities big and small, throughout the South and wherever Southerners ended up, as much as it was in the country. And though rural America is endlessly mythologized today in modern country music, the city is still at the heart of country, and still a source of new inspirations and influences on the traditions. On Baby You Win, Cliff Westfall brings his Kentucky roots to a very urban New York world, opening up the old country sounds to a much wider vision of Americana.