By: Alex Brook Lynn
March 16, 2023

One in a series of 25 enthusiastic posts, contributed by 25 HILOBROW friends and regulars, on the topic of favorite Country singles from the Sixties (1964–1973). Series edited by Josh Glenn. BONUS: Check out the DOLLY YOUR ENTHUSIASM playlist on Spotify.



I grew up in New York City during the 1990s, a head-down headphone era. Hip-hop beats and jazz horns made the perfect soundtrack for bouncing up and down flights of stairs and running for trains. New York City was less a part of the US and more the capital of the world. In 2001, when I first heard “The Winner” by country-folk man Bobby Bare, I was eighteen years old; before then, I barely thought of myself as an American.

“The Winner” is a rhyming story-song with a punchline, featuring fictional hero Tigerman McCool. He’s an aging tough guy at a local dive bar who schools the narrator, a young contender, on the folly of barroom brawling for street cred. Old toughs comically aware of their own futility was what I grew up around… only my dad and uncles were Jewish criminals from Brooklyn.

Bobby Bare had come back to RCA Records in 1973 specifically to work with Shel Silverstein. He’d had a bunch of success since the late 1950s with songs adjacent to country but categorized more as folk. He had a honey tone to his voice that made him universally comforting, resigned but jolly. His tunes were sentimental. Shel was a Chicago-born children’s book writer who had spent the early ’70s penning some of country’s most cherished anthems.

The song was released on the album Lullabys, Legends and Lies in November 1973, a few months after the last US troops left South Vietnam. The war destroyed faith in the great mythos of American masculinity and its value as the world’s savior, a set of beliefs codified after World War II with its definitive victory over a clear enemy. Tigerman looks at the narrator, “with his knuckles clenching white,” and decides against an ass-kicking in favor of mocking the glory that the younger man seeks. It’s hard not to imagine Bobby and Shel, having already served in a forgotten war, regarding the boys signing up for Vietnam in a similar fashion.

Silverstein could lyrically twist human suffering and preciousness around each other like a candy cane. The result was an album that felt like a morality play told by a comic to a kindergarten class. It made me feel like there was a continuity between us in a vast unending Americanness.

“The Winner” was a gateway, for me, into post-“Golden Era” Nashville country. I had found this kind of music a few months before the September 11th attacks, when I would be introduced to America in body and spirit. New York City had, after all, officially become part of the U.S. that day. A short time later I learned to drive, and traveled south for the first time in my life. As the new wars began, I was lost and directionless, and began to appreciate sounds from a world more used to highways and quiet dusks, houses on dirt roads, and the levity in life-long drinking habits.


DOLLY YOUR ENTHUSIASM: INTRODUCTION by Josh Glenn | David Cantwell on Porter Wagoner and Dolly Parton’s WE FOUND IT | Lucy Sante on Johnny & June Carter Cash’s JACKSON | Mimi Lipson on George Jones’s WALK THROUGH THIS WORLD WITH ME | Steacy Easton on Olivia Newton-John’s LET ME BE THERE | Annie Zaleski on Tammy Wynette’s D-I-V-O-R-C-E | Carl Wilson on Tom T. Hall’s THAT’S HOW I GOT TO MEMPHIS | Josh Glenn on Commander Cody and His Lost Planet Airmen’s BACK TO TENNESSEE | Elizabeth Nelson on Skeeter Davis’s I DIDN’T CRY TODAY | Carlo Rotella on Buck Owens’ TOGETHER AGAIN | Lynn Peril on Roger Miller’s THE MOON IS HIGH | Erik Davis on Kris Kristofferson’s SUNDAY MORNIN’ COMIN’ DOWN | Francesca Royster on Linda Martell’s BAD CASE OF THE BLUES | Amanda Martinez on Bobbie Gentry’s FANCY | Erin Osmon on John Prine’s PARADISE | Douglas Wolk on The Byrds’ DRUG STORE TRUCK DRIVIN’ MAN | David Warner on Willie Nelson’s WHISKEY RIVER | Will Groff on Tanya Tucker’s DELTA DAWN | Natalie Weiner on Dolly Parton’s IN THE GOOD OLD DAYS (WHEN TIMES WERE BAD) | Charlie Mitchell on Stonewall Jackson’s I WASHED MY HANDS IN MUDDY WATER | Nadine Hubbs on Dolly Parton’s COAT OF MANY COLORS | Jada Watson on Loretta Lynn’s DON’T COME HOME A DRINKIN’ (WITH LOVIN’ ON YOUR MIND) | Adam McGovern on Johnny Cash’s THE MAN IN BLACK | Stephen Thomas Erlewine on Dick Curless’s A TOMBSTONE EVERY MILE | Alan Scherstuhl on Waylon Jennings’s GOOD HEARTED WOMAN | Alex Brook Lynn on Bobby Bare’s THE WINNER. PLUS: Peter Doyle on Jerry Reed’s GUITAR MAN | Brian Berger on Charley Pride’s IS ANYBODY GOING TO SAN ANTONE.




Country, Enthusiasms, Music