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Kenny Rogers: 10 Essential Songs

From his signature “The Gambler” to duets with Dottie West, Kim Carnes, and Dolly Parton

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Upon in his induction in 2013, Kenny Rogers — who died on March 20th, 2020 at the age of 81 — was one of the Country Music Hall of Fame’s most deserving modern inductees, with more than 100 million records sold, 21 country music Number One hits, and multiple pop chart-toppers. Still, a select few of those songs stand above the rest in his catalog. Here we compile his 10 essentials, from his signature “The Gambler” to duets with Dolly Parton, Dottie West, and Kim Carnes.

Editor’s note: This story was originally published in March 2020.

From Rolling Stone US

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“Just Dropped In (To See What Condition My Condition Was In)” (1967)

For all of the softer material Rogers produced in the late Seventies and early Eighties, it’s easy to overlook the fact that the dude knew how to rock. With his band the First Edition, Rogers got in on the psychedelic craze of the late Sixties, turning a Mickey Newbury song about dropping acid into a swirling, hallucinatory masterpiece. Kicked off by some coiling backwards guitar courtesy of Glen Campbell, it rushes in with those watery “yeah” vocals, stuttering, funky drums, and doubled-up stabs of organ and electric guitar — fitting accompaniment for a bad, bad trip where a numb-sounding Rogers “saw so much I broke my mind.” It later wound up accompanying a sublimely strange dream sequence in the Coen Brothers’ beloved The Big Lebowski. The Dude definitely abides. J.F.

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“Lucille” (1977)

In 1976, Rogers launched a solo career that got off to a slow start with the LP Love Lifted Me. When his self-titled sophomore record was issued, its lead single barely cracked the Top 20. But the next one would connect, topping the country chart, reaching Number One in the U.K., and turning nine simple words into one of the most easily identifiable country-song choruses of the 20th century: “You picked a fine time to leave me, Lucille.” Rogers soberly narrates the Toledo barroom saga of a married-but-miserable couple who separately drown their sorrows, before confronting each other, with Rogers uneasily stuck in the middle. The husband gone, Rogers and Lucille head for a hotel room, but he calls off their tryst as the husband’s pitiful words reverberate in his head, having already observed how Lucille made this quivering mountain of a man “look small.” S.B.

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“Ruby, Don’t Take Your Love to Town” (1969)

Rogers and the First Edition’s country affinities came through loud and clear with this Mel Tillis tune, released in 1969 in the midst of the Vietnam War. The gut-churning narrative (actually derived from a Korean War-era story) centers on a soldier who loses his legs in battle and returns home to find that his wife would prefer to spend time with other men, adding a layer of psychological pain to his physical wounds. For as upbeat — almost jaunty — an arrangement as it is, Rogers imbues “Ruby” with an unmistakable ache as he pleads for his love to stay and keep him company. When she refuses and slams the door, the darkness bubbles up inside him: “If I could move I’d get my gun and put her in the ground,” he sings. Absolutely chilling. J.F.

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“Lady” (1980)

There’s an alternate timeline where Lionel Richie decides to keep “Lady” for himself and it launches the Commodores singer’s solo career into the stratosphere. But in this one, Richie’s smoldering admission of desire and devotion went to a red-hot Rogers and became the crossover country singer’s biggest commercial success (plus Richie ending up doing fine for himself anyway). Built off a cascading minor-key piano melody, “Lady” is the ideal balance of Rogers’ tough and tender sides, his voice cracking in all the right places but never once sounding feeble or uncertain about confessing his feelings. It swells up to a lush, pillowy production of sighing strings and languid electric guitars — all satin sheets and flickering candlelight. This is, as the kids say, a big mood. J.F.

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“Islands in the Stream” (1983)

Penned by the Bee Gees’ brothers Barry, Maurice, and Robin Gibb, this effervescent, sweetly romantic duet was a global smash for Rogers and Parton. Co-produced by Barry Gibb for Rogers’ Eyes That See in the Dark album, the result is a superb chiaroscuro of Parton’s bubbly optimism and Rogers’ grainy realism. Yet the two singers ride the crests and troughs of the song’s melody in perfect sync, finding each other’s inner strengths and softness at the same time. Platinum-selling in the U.S. (denoting sales in excess of two million), the single topped the pop and country charts, becoming the best-selling country hit of 1983 and giving Rogers his second Number One pop tune. S.B.

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“Coward of the County” (1979)

Rogers’ cinematic 1979 hit “Coward of the County,” penned by Roger Bowling and Billy Ed Wheeler, has no right to be as funky as it is — half of the band seems to be playing it straight, while the bassist and guitar player apparently have other ideas. It belies the fact that it’s a pitch-black tale about a young pacifist who spends his life adhering to his father’s advice to turn the other cheek until the day when those Gatlin boys “took turns” (a polite, radio-friendly euphemism for rape that’s still jarring) with his girlfriend Becky. That’s when he learns to temper his father’s lessons with his own hard-won wisdom: “sometimes you gotta fight when you’re a man.” If you can make an entire movie from a four-minute song, you’re onto something. J.F.

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“The Gambler” (1978)

Kenny Rogers wasn’t the first to record it — that would be Bobby Bare in 1976, followed in close succession by its songwriter Don Schlitz, then country legend Johnny Cash. But what Kenny Rogers did with “The Gambler” would transform and transcend his efforts as a recording artist, laying the groundwork for a series of TV films in which he starred as Old West card player Brady Hawkes. Like “Lucille” before it, “The Gambler” was a story-song, but its railroad-car setting proved more ethereal, even ominous, as the title character dispensed lifelong wisdom before shuffling off this mortal coil and, in gambling parlance, “breaking even” in the car’s gloomy darkness. Decades after the song topped the country chart and reached pop’s Top 20, it remained a key element of Rogers’ brand, often covered but never quite duplicated. And it’s a safe bet it never will be. S.B.

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“Don’t Fall in Love With a Dreamer” (1980)

Kenny Rogers was already a crossover success in early 1980 when he issued Gideon, an ambitious concept album that chronicled the life of a modern-day cowboy named Gideon Tanner. Written at Rogers’ request by songwriter Kim Carnes — two years before she recorded “Bette Davis Eyes” — with her husband Dave Ellingson, Gideon cast Rogers as a cattle rustler with an eye for the ladies, and a wandering eye at that. A country-pop power ballad with no fairytale ending in sight, “Dreamer” finds two lovers facing a doomed future, their sadness and regret tinged with gritty resolve. Rarely have two singers been so beautifully matched — and so utterly heartbreaking. The sole single from Gideon, “Dreamer” gave Rogers his fifth Top 10 pop entry in the U.S. S.B.

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“Every Time Two Fools Collide” (1978)

Both signed to the United Artists label, Kenny Rogers and Dottie West were nevertheless at very different points in their respective careers when they first sang together in late 1977. Rogers was on a hot streak, basking in the crossover success of “Lucille” and “Daytime Friends,” while West, a solo country star since 1964, hadn’t scored a major hit since 1974. But with “Every Time Two Fools Collide,” the dusky-voiced Tennessean who had previously teamed with Jim Reeves, Don Gibson, and Jimmy Dean met something of a musical soulmate in her Texas-born counterpart. With strings and steel, this is more of a throwback to earlier country pairings, as two outstanding interpreters forge an easy camaraderie, which would ultimately result in four Top Five singles and a pair of consecutive CMA Vocal Duo of the Year honors. S.B.

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“Buy Me a Rose” (1999)

Rogers’ final country chart-topper was a late-career comeback in 1999 that arrived more than a decade after his previous Number One. Written by Jim Funk and Erik Hickenlooper, the story is well-suited for Rogers to tell: man tries to express his love with fancy material things, woman just wants him to say the words and do the little stuff, guy eventually figures it out and vows to stop holding all those feelings inside. Rogers is joined by the unlikely pairing of country singer Billy Dean and bluegrass star Alison Krauss, who provide the heavenly backing vocals on the simple, elegant recording. For a time, it gave the then 61-year-old Rogers a record as the oldest person to have a country Number One (Willie Nelson passed him later), putting an exclamation point on a career that stretched back to the late Fifties. J.F.