Keith Whitley‘s brief solo career, cut short by his 1989 death from alcohol poisoning, gifted country music fans with some of the greatest old-school country songs of the ’80s. It’s not hyperbole to rate his songs as highly as some of George Strait and Randy Travis‘ best-loved classics. Sadly, fans can only wonder how Whitley’s ’90s output might’ve stacked up against such fellow traditionalists as Alan Jackson and Clint Black.
Despite passing away at the young age of 33, Whitley’s career spanned nearly 20 years. Whitley and fellow Kentucky native Ricky Skaggs became fast friends as young teens after meeting at a bluegrass festival. The two talented friends broke into the music business together in the 1970’s as the junior members of Ralph Stanley’s Clinch Mountain Boys. He later handled lead vocals for J.D. Crowe and the New South, a run defined by a really great cover of Jonathan Edwards’ “Girl From the Canyon.”
In 1983, Whitley relocated to Nashville to pursue a solo career. After three years of ups and downs, Whitley arrived as a genuine superstar with 1986 album LA to Miami. The next three eventful years, and a pair of posthumous releases, dominate the following rundown of one of modern country’s music most talented and tragic figures’ greatest hits.
“Turn Me to Love”
RCA tested the mainstream waters for Whitley with the six-song EP A Hard Act to Follow, which lacked the focus of future releases. In retrospect, opening track “Turn Me to Love” previewed Whitley’s mastery of blending the old with the new, crossing old school guitar work and South of the border flair with catchy, radio-friendly lyrics.
“The Birmingham Turnaround”
This deep cut name drops an Alabama city while sounding more Texas than Tennessee. Meaning, the Tom T. Hall-style story-song sounds more like something a red dirt underdog might’ve performed at the time than a ready-made hit for one of the toasts of Nashville.
“Miami, My Amy”
A love song built around a clever play on words signaled Whitley’s arrival as a genuine country star. The song has aged well for the most part, although the once-poetic line “even in my taxi I could hear my telephone ring” takes a second to process in the age of smart phones.
Whitley’s back catalog reflects a variety of approaches to country music, including this rocking honky tonk stomper that wouldn’t sound out of place in a rockabilly band’s repertoire. Whitley revisited his rowdy side as a musician two singles later with the equally heavy-hitting “Some Old Side Road.”
This highlight of posthumous album Kentucky Bluebird pairs Whitley with one of his greatest hit-making peers, Earl Thomas Conley. The pair wax nostalgically about brotherly bonds and sibling rivalries, the type Keith surely shared with another talented performer, Dwight Whitley.
“When You Say Nothing At All”
Whitley didn’t write the best love song among his chart-topping singles. That credit belongs to Paul Overstreet and 2017 Country Music Hall of Fame inductee Don Schlitz. Yet its easy to imagine Whitley felt every word when he fell in love with Lorrie Morgan.
“Tell Lorrie I Love Her”
A raw acoustic demo included on a posthumous greatest hits collection allowed Whitley to provide his fans and his widow, fellow country singer Lorrie Morgan, with these fitting last words. For a real tear-jerker, revisit Jesse Keith Whitley’s live duet with his mom.
“Til a Tear Becomes a Rose”
Marriage partners became an old-fashioned family singing duo when Lorrie Morgan’s voice was added to this song after Whitley’s passing, making for a memorable and gut-wrenching single that helps define both artists’ careers.
“Don’t Close Your Eyes”
When it comes to sad songs, “Don’t Close Your Eyes” ranks up there with Garth Brooks’ “The Dance.” Both songs’ intro alone leaves at least one fan out there scrambling for the tissue box. As a side note, the original video for “The Dance” includes a brief tribute to Whitley.
“I’m No Stranger to the Rain”
Anyone successfully overcoming bouts of depression will understand these lyrics loud and clear. Whitley sings conquering life, even when it felt like proverbial storm clouds followed him around. The song is referenced in another modern classic, “Go Rest High on that Mountain,” written by Vince Gill in reaction to Whitley’s death.