Over the more than 60 years that Kenny Rogers wrote songs, his trajectory defied any straightforward narrative. Yes, he’s a Country Music Hall of Famer; yes, one of his best-known and most enduring songs is a trippy ode to LSD. He started his career playing bass in jazz and R&B bands in his native Houston; his first single, 1958’s “That Crazy Feeling,” was a convincing enough doo-wop performance to earn young Kenneth an appearance on American Bandstand. A half-century later, he was best known as either The Gambler, or a crowd-pleasing pop singer-turned-fried chicken magnate.
His journey through commercial jazz with the New Christy Minstrels and quasi-hippiedom with the folk/rock/pop of the First Edition is wild in the context of his later hits, until you think about how diverse those hits are. “The Gambler” and “Lady” were released within two years of each other, but Rogers never saw his aesthetic omnivorousness as a liability. “I’ve always been country, but not strictly,” Rogers said in 1978. “When I look at a song, I look at it as a hit, and not as a particular kind of music.” Once you know that, the wide-ranging glut of very successful songs Rogers produced, and the millions of copies they sold, makes even more sense. Rogers perpetually played down his abilities as a singer, insisting that he wasn’t a technician but a stylist. However he preferred to describe it, his ability to sell just about any kind of pop song – to make you not just like it, but feel it – was nearly unmatched. Here are 20 of his best.
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20: If You Want To Find Love, Back Home Again (1991)
One of the most straight-forwardly country songs on this list, “If You Want To Find Love” proves Kenny Rogers’ Nashville mettle: a nostalgic, mandolin-adorned story song that actually counsels against cheating. It’s warm and familiar without sounding at all redundant, and has polished production that’s proven remarkably trend-resistant. Rogers’ smoky voice sounds fully folksy here, not cabaret – a rebuke of those who might question his country bona fides.
19: Don’t Fall In Love With A Dreamer, Gideon (1980)
A concept album about a Texas cowboy should have been a career-crystallizing moment for The Gambler – though it wasn’t quite that, Gideon did produce this, Kenny Rogers’ fifth top-five single on the Hot 100. It’s a convincing, relatively unadorned ballad that features Rogers’ reunion with Kim Carnes, who co-wrote all the songs on Gideon. The two had worked together back in the early 60s when they were just starting out, and their vocal chemistry allowed Rogers to stretch out and show off his skills for anyone who might have doubted his abilities as a powerhouse singer.
Kenny Rogers, Kim Carnes - Don't Fall In Love With A Dreamer (Audio)
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18: I Prefer The Moonlight, I Prefer The Moonlight (1987)
So much of Kenny Rogers’ post-Bee Gees output was built solely for success at adult contemporary radio. That’s not inherently a bad thing, but it does make many of his songs from the mid-’80s to early 90s sound, retrospectively, very, very similar, with strings, gentle synths, and balladry featuring prominently. That made “Moonlight,” with its folk-rock-tinged eclecticism and extended, loose format all the more refreshing. The track, which reached No. 2 on the Billboard country charts, is sultry and fun, showcasing virtuoso Mark O’Connor on mandolin and fiddle as well as Rogers’ frequent collaborator Kim Carnes on background vocals. It’s country pop at its most expansive and creative, and as a result, at its richest.
17: Tennessee Bottle, The Gambler (1978)
Kenny Rogers’ most obvious reaches outside of his own down-the-middle pop and country comfort zones – aside from a few dalliances with the period’s lite reggae – came with his various disco experiments. They are often maligned, but Rogers, as evidenced by “Bottle,” married his country background with the loosest hint of a disco groove in a way that felt organic and actually less saccharine than many of his straight-ahead pop tunes. Not just on “Bottle,” but on “So In Love With You,” “The Fool In Me,” “You Turn The Light On,” and more, Rogers pushes toward the dancefloor in his own distinct way.
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16: Love Or Something Like It, Love Or Something Like It (1978)
It’s not at all hard to imagine Kenny Rogers, who was married five times, penning the line “Show me a bar with a good-lookin’ woman/Then just get out of the way.” It’s more surprising that, alongside his longtime bandmate Steve Glassmeyer and the producer who brought him his earliest solo success, Larry Butler, Rogers managed to make this memoir of a barroom lothario so charming. With its calypso lilt and earthy bassline, the song feels different than most of Rogers’ hits. (It became his third No. 1 on the country charts.) The chorus’ centerpiece, “It’s cheap but it ain’t free,” adds a perfect sour, real note to the otherwise upbeat ode to free love.
15: Coward Of The County, Kenny (1979)
Most top ten hits, thankfully, don’t have a gang-rape scene, but the momentum Kenny Rogers had after the success of “The Gambler” the year prior made attempting to recreate this song almost line for line a no-brainer. Unsurprisingly, it worked. “Coward” was an even bigger success than “The Gambler,” reaching No. 3 on the Hot 100 and becoming one of Rogers’ signature songs, as well as providing even more ammunition against anyone who might have questioned his country credibility. If it’s not the strangest song to become one of the biggest in the country, it’s certainly one of the most gruesome.
14: Every Time Two Fools Collide, Every Time Two Fools Collide (1978)
Allegedly the product of a happenstance meeting at a Nashville studio, this duet with Dottie West sparked two collaborative albums and became the first of four top-five Billboard country hits for the pair. A classic pop vocal showcase with pedal steel punctuation and an epic scale, the track has become one of the most beloved duets in country history. Perhaps because neither artist was at the beginning of their career when they recorded the song, they were able to give its theme – a relationship that just isn’t working – an ever more convincing, world-weary portrayal.
13: While The Feeling’s Good, Love Lifted Me (1976)
From a commercial perspective, this single – which predated Kenny Rogers’ big break on the country charts – was a flop. Aesthetically, though, it proved how effectively Rogers could fit into the Nashville Sound, combining its gloss and pathos with a modern, gentle groove. It’s a peek at country’s sexy side, one that Rogers didn’t often tap into. Instead, he tended to fit his boudoir-ready tracks into a pop or R&B mold. “While The Feeling’s Good,” though, is a taste of the road not taken, and how great Rogers sounds crooning alongside a pedal steel.
While The Feeling's Good
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12: Love Will Turn You Around, Love Will Turn You Around (1982)
Released around the zenith of Kenny Rogers’ success, “Love Will Turn You Around” was nevertheless an exercise in understatement. An easy acoustic riff drives the song while Rogers spins a familiar yarn about the transformative power of love. He is a true master of conversational singing, making a fairly standard melody and song structure irresistible with seemingly little effort. The folksy vibe of the song was a welcome throwback to Rogers’ earlier work, and it reached No. 1 on both the Billboard country and adult contemporary charts – the fourth time a Rogers tune had reached both peaks.
11: You Can’t Make Old Friends, You Can’t Make Old Friends (2013)
It’s hard to listen to this song, a duet with Dolly Parton, in the wake of Kenny Rogers’ passing. Yes, it’s filled with the kind of sentimentality that would probably be cringeworthy if it weren’t coming from two old, legendary artists who are, in fact, old friends. But the stripped-down arrangements and earnest delivery make it gutting, a sincere reflection on mortality from two people who have seen more together than most of us will probably ever understand. Parton’s tearful memorial to Rogers seemed to give this song even more meaning – a chance to not just say but sing those same sentiments to (and with) Rogers while he was still living.
10: Share Your Love With Me, Share Your Love (1981)
To sing a song after Aretha Franklin not just sang it, but won a Grammy for her performance, takes bravery. But when Kenny Rogers had the biggest single of his career singing the Lionel Richie composition “Lady,” he elected, unsurprisingly, to continue making his own brand of pop R&B. He gave Richie the reins for his next album, the underrated Share Your Love, which still serves as effective proof of how country and R&B are only as far apart as record labels – and racism – make them. Rogers is joined by Gladys Knight and the Pips as well as Richie himself on the title track, which climbed the charts easily. It remains a premier example of genre-agnostic pop gloss.
Share Your Love With Me
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9: She Believes In Me, The Gambler (1978)
“She Believes In Me” has the kind of chorus that sticks in your head even if you don’t think you’ve ever heard it before, which helps account for how this single became Kenny Rogers’ first AC No. 1 and the biggest hit of his solo career to that point. It could hardly sound more different from “The Gambler,” which it followed, but fans embraced it nevertheless – early evidence of Rogers’ versatility.
8: Ruby Don’t Take Your Love To Town, Ruby Don’t Take Your Love To Town (1969)
A rollicking down-home tune with a perfectly singable chorus, “Ruby” and its performative, upbeat, folksiness serve as a Trojan horse for a surprisingly grim tale. The narrator, husband of the titular Ruby, has been wounded in the “crazy Asian war” (given the timing, assuming it was Vietnam would be fair – but the author, Mel Tillis, says it was inspired by World War II) and so Ruby has started seeking affection elsewhere. The first hit credited to “Kenny Rogers and the First Edition” rather than just The First Edition, “Ruby” fittingly featured Rogers front and center as a gruff but relatable everyman (except, perhaps, the line when he threatens to “get my gun and put her in the ground”).
7: Evening Star, Eyes That See In The Dark (1984)
With Barry Gibb as head producer, it would be fair to have expected an album full of the disco experiments that Kenny Rogers was already making long before the Gibbs came into the picture. But Eyes That See In The Dark is more polished pop than anything else, with a front-to-back consistency that many of Rogers’ albums, with their laser focus on creating huge hits, lack. “Evening Star” is one of the album’s most “country” entries, with the Gatlin brothers singing backup and a decidedly Western focus. Lilting and gentle, it’s straightforward and, simply, pretty.
6: Sweet Music Man, Daytime Friends (1977)
Nothing about “Sweet Music Man” says “major hit,” as has been proven by the tepid responses to not just Kenny Rogers’ multiple releases of the track, but covers by artists from Dolly Parton to Reba McEntire. Nonetheless, the Rogers-composed tune keeps getting covered, its sweet melody and meta refrain (“Nobody sings a love song quite like you do”) charming artists of all generations. It’s the most enchanting critique of the music industry’s cynicism you’ll ever hear.
5: Lucille, Kenny Rogers (1976)
The mythology of “Lucille” is that Kenny Rogers, newly solo after his tenure with The First Edition, was doing gigs as a Vegas lounge act and advertising music lessons when he found it in a pile of cast-off songs in a Nashville publishing office. The song is so seamless and self-evidently catchy it’s hard to really believe that rags-to-riches tale. Either way, the song reached No. 5 on the Hot 100 and became his breakthrough solo hit – creating an acoustic, folksy template that Rogers would draw from again and again. And why not? It sounded like the song he was born to sing, and who doesn’t want to sing along to, “You picked a fine time to leave me, Lucille”?
Kenny Rogers - Lucille (Audio)
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4: Lady, Kenny Rogers’ Greatest Hits (1980)
If Kenny Rogers wasn’t explicitly aware of the quiet storm movement in R&B, Lionel Richie, who wrote and produced what would become the biggest single of his career, certainly was. It comes through in “Lady,” which has the same kind of super-slow tempo and conversational balladry as some of the sultrier R&B hits of the day. The song was enormous, staying atop the Hot 100 for six straight weeks and charting on not only the AC and country charts, but the soul chart as well. It cemented Rogers’ status as a bona fide pop star as much as a country singer, and showed that Richie had more than enough talent to make it as a solo act himself.
Kenny Rogers - Lady (Audio)
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3: Just Dropped In (To See What Condition My Condition Was In), The First Edition (1967)
In keeping with what would become his own musical non-tradition, Kenny Rogers’ first major hit song alongside the First Edition was odd – a psychedelic rock tribute to LSD that would become the theme song for a generation of hippies (or at least the news reels that captured them) and Big Lebowski fans. It’s a noisy, experimental, strange song that doesn’t sound as popular as it was, but it reached No. 5 on Billboard’s Hot 100 as the band’s second-ever single. It’s not just a massive song, but a pop culture touchstone – shorthand for a whole generation’s trippy proclivities. And Rogers is, as ever, totally convincing, even though his role might as well have been on Mars compared to the one he played during his greatest solo success.
Just Dropped In (To See What Condition My Condition Was In)
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2: Islands In The Stream, Eyes That See In The Dark (1982)
There might be no happier hit song than this one, an easy post-disco monolith seemingly perfectly tailored to both Kenny Rogers’ and Dolly Parton’s particular take on pop-via-country. It was originally penned, according to the Gibb brothers, for Marvin Gaye, but it’s hard to imagine anyone else selling its friendly idiosyncrasies so well (“I set out to get you with a fine-tooth comb”?). Kenny and Dolly were an incredibly appealing duo, and “Islands” serves as an enduring tribute to their camaraderie – as well as a good retort to anyone who might get too bogged down in country orthodoxy.
1: The Gambler, The Gambler (1978)
You know the song, and you know the chorus. If you’ve been in a bar anytime in the past four decades, you’ve probably sang it a few times. Don Schlitz penned an epic tale that, despite having already been recorded by Bobby Bare and Johnny Cash, didn’t become ubiquitous until Kenny Rogers etched it into the history books. The production is impeccable, and Rogers’ performance is understated enough to goad a million fans into exhorting each other to know when to hold ‘em and know when to fold ‘em. It takes a pretty powerful song to completely define its singer, especially when that singer is someone who was already as familiar and established as Kenny Rogers. Nevertheless, Kenny is The Gambler. Wise, benevolent, catchy as anything – there are a lot worse places to wind up.
Kenny Rogers - The Gambler
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