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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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“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.