17. Patty Loveless – “How Can I Help You Say Goodbye”
Patty Loveless is my favorite country singer of the 1990s. Though strongly influenced by country giants like George Jones, Loveless phrases songs so uniquely that I can’t imagine anyone else singing her songs with as much wisdom and care. With a stately melody and arrangement driven by piano and strings, “How Can I Help You Say Goodbye” embodies her approach. Illuminating lessons learned from a daughter’s childhood through her mother’s death, this song is one of Loveless’ best-remembered hits. Another Patty Loveless contender for this list, “You’ll Never Leave Harlan Alive,” is also a masterpiece, but “How Can I Help You Say Goodbye” typifies the kind of songwriting and singing that is among the best of the past 40 years. No wonder Rolling Stone called her the best country singer alive.
16. Vern Gosdin – “Chiseled in Stone”
One of the most chilling and haunting records I’ve ever heard, “Chiseled in Stone” captures love’s hard lessons with Vern Gosdin’s choked-up vocal performance. Words from an old man who has lost his love send the singer running back to his own, as Gosdin sings that he has been told, “You don’t know about lonely ’til it’s chiseled in stone.” This recording is an example of country music heartbreak at its finest.
15. Lucinda Williams – “Lake Charles”
Lucinda Williams, once called America’s best songwriter by Time magazine, has written prolifically about death, including in such masterpieces as “Pineola” and “Drunken Angel”. But true to form, “Lake Charles” is unusually affecting. Maybe my favorite song on the celebrated masterpiece Car Wheels on a Gravel Road from 1998, “Lake Charles”, is heartbreaking in its understated treatment of a friend’s suicide. With Cajun-style accordion and dobro, the stripped-down recording evokes its Louisiana namesake with some of the most affecting songwriting out of any Americana scene.
14. Vince Gill – “Go Rest High on That Mountain”
A country gospel classic, “Go Rest High on That Mountain”, might be Vince Gill’s greatest triumph. A virtuoso instrumentalist, singer, and songwriter, Gill wrote part of this song as a tribute to the late country great Keith Whitley and returned to it years after his brother’s passing. His vocal on this recording is restrained, as are the instrumental parts, and the chorus soars with harmonies from fellow country giants Patty Loveless and Ricky Skaggs.
13. Bill Monroe and His Bluegrass Boys – “Uncle Pen”
Whether or not Bill Monroe is the father of bluegrass music, his recordings highlight the classic bluegrass style. Best known because of Ricky Skaggs’s hit cover, “Uncle Pen” is a stellar example. A fiddle showcase featuring mandolin and close high vocal harmonies, the recording is ebullient, including in memorializing the death of Monroe’s beloved uncle. As the bounce of “Uncle Pen” proves, sometimes the best way to remember a departed loved one is to dance the night away.
12. Keith Whitley – “Tell Lorrie I Love Her”
This stark home recording became the epitaph of Keith Whitley after his untimely death from alcoholism in 1989. Loosely based on the decades-old hit, “Tell Laura I Love Her”, Whitley’s poignant ode to his wife, fellow country star Lorrie Morgan, always gives me chills. Eerily prophetic, Whitley imagines what his last words would be. This recording belongs with such Whitley classics as “Don’t Close Your Eyes” and “I’m No Stranger to the Rain” in the country music canon.
11. Martina McBride – “Independence Day”
Not only did “Independence Day” provide Martina McBride with an unusually perfect vehicle for her singing, but it also changed country music in the 1990s. Like Garth Brooks’ “The Thunder Rolls”, the lyrics don’t state that death happens following domestic violence. Still, the videos for both songs show death, and without this crucial record, I suspect that other songs about domestic violence, including McBride’s “Concrete Angel” and Jason Michael Carroll’s “Alyssa Lies,” would never have been made. To this day the electric force in this recording is overwhelming.
10. Merle Haggard & the Strangers – “Sing Me Back Home”
For many, Merle Haggard was and is the epitome of a country artist. With his pared-down Bakersfield Sound arrangements, terse lyrics, and moving but restrained vocal approach, Haggard became known as “the poet of the common man”, and “Sing Me Back Home” shows his style at its best. In it, he recounts a death row inmate who wants his “guitar-playin’ friend” to help him sing music from his youth before he is executed. “Sing Me Back Home” is a masterpiece of a recording, and among his other hits for Capitol, including “Mama Tried” and “Hungry Eyes”, it defines country music for many listeners.