Keith Whitley was one of country's greatest romantics. His songs bleed with longing and clarity in its love for a woman. The sad songs remain as devastating as ever, endless metaphors and analogies for the end of a relationship. His greatest love songs throb and ache for a true lover.
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Many country artists after Whitley would study and utilize what makes his records so great. I think of Tracy Lawrence "Can't Break It To My Heart" and how his country drawl howls on the chorus. In another universe, I hear Keith and his tender croons on 90s country ballads with Shania Twain, Faith Hill, or Reba McEntire.
Unfortunately, we lost Whitley far too soon. Before his big invite to the Grand Ole Opry, Keith passed away at 34 years old from alcohol poisoning. Who knows how seamlessly he would've transitioned into the decades that followed? Regardless, as one of the defining country artists of the 80's, it's only right to narrow down his greatest songs. Here's the Keith Whitley Mount Rushmore, the four records that represent the cream of the crop.
The Four Best Keith Whitley Songs of All Time
"Homecoming '63"
This is the kind of earnest cheesiness that gives the 80s so much of its color. The tender synth chords, the saxophone that sounds like Kenny G or any number of classic sitcoms at the time. In this set of circumstances, it's perfect though. It seamlessly matches how Keith reminisces over a past love at a high school homecoming. He dramatically spotlights their dances together and imagines the whole room fawning over how perfect the pair are together. Then, Whitley warmly caps it off with how magical their hook up was in his old '57. It sounds a little silly and overblown in the hands of a lesser singer. With Keith, it reawakens the memories we still cherish.
"I'm No Stranger to the Rain"
Typically, people give all the credence to the lord and their faith. Conversely, they might chalk something up to the mysteries of the universe. However, Keith taps into something really special here. Whether we know it or not, there's a ton of strength we don't always fully tap into at our lowest. The darkest moments show our test of character and we could do more to give credence to our monumental efforts.
"I'm No Stranger to the Rain" sees Whitley ponder the depths of despair. Moreover, he emphasizes that this isn't an unfamiliar valley for him to undertake. "I've fought with the devil, got down on his level. But I never gave in, so he gave up on me," Keith sings to a crisp guitar riff.
It's a true testament to the perseverance in all of us deep down. No matter how hard it rains, we hold great potential to weather any storm. We simply must find it in ourselves to believe it.
"Kentucky Bluebird"
There's an endless supply of sad songs. Keith Whitley made an abundance of them throughout his career. There's only so many different ways to skin this type of song. Lots of 'I miss you' and 'please come back to me' phrases echoing in the fabric of these records. However, I've never known an artist to actualize this feeling through the act of a bird flying away. That feels impossible. Moreover, it seems even less likely that an artist wouldn't make it sound far too corny.
Somehow, Whitley avoids the inevitable eye rolls that comes with a concept that is so on the nose. Perhaps it's his inimitable ability to harmonize his vocals so they swell on the hook. On a writerly basis, I admire his ability to navigate inserting poignant detail with something staggeringly simple. "Blue is a feeling I'm learnin' so well. Turn on the TV in another hotel, turn down the volume and stare at the wall. God, I wish you would call," Keith croons.
It's vivid writing, the agony of missing someone you know isn't around and won't come back around. So when he calls out for the titular Kentucky Bluebird, you can sense it's something he could only imagine. The song doesn't neatly resolve itself either. Instead, he merely reflects on the dream he had of him and his lover holding one another. That's the closest he can get to reclaiming that feeling amidst the space.
"Miami, My Amy"
A lot of artists struggle to capture the essence of anywhere that's not the great wide open country. Plenty of artists desperately try to get their Jimmy Buffett on and travel to Margaritaville in their songs. However, most of them generally come off like they're stampeding the beach to crack open cheap brews and get sunburnt. Rather than bask in what the area provides, they attempt to submit their surroundings to their hardheaded instincts. Keith Whitley's "Miami, My Amy" preserves the Floridian breeze and swaying palm trees and funnels it through the promise of throbbing love.
"Miami, My Amy" preserves that familiar 80s cheese that makes "Homecoming '63" so great. The twang registers a bit more anonymously but in this context, I think it works. Whitley's drawl adds to the dizzying flights from Los Angeles to Miami. You can remove a man from the country but you can't take the country out of Keith.
The constant in Whitley's music lies in the earnestness that informs his throbbing yearning for the titular Amy. It's so hopelessly romantic, burning flight money to Miami to preserve the flame between the two. It's the perfect embodiment of 80s love songs, wholehearted, almost delusional affection that Keith specialized in. Country has been trying for years to siphon the feeling he evoked so naturally.
