A very prominent CountryMusic singer known for his string of crossover pop ballads. Kenneth Donald "Kenny" Rogers (born 1938) got his start in the 1960s folk group The New Christy Minstrels. By 1967, he was part of the rock group The First Edition, which had major pop hits with "Just Dropped In (To See What Condition My Condition Was In)" and "Ruby, Don't Take Your Love to Town". Rogers broke off in 1975 to start his own career, launching it with a cover of the gospel standard "Love Lifted Me". It wasn't until two years later that he broke through, sending a string of singles to the top of the charts and achieving consistent pop and adult contemporary airplay for each. Among his hits in the late 1970s and early 1980s were "Lucille", "The Gambler", "She Believes in Me", "Coward of the County", "Lady" and "Islands in the Stream", a duet withMusic/DollyParton. The last two have the distinction of being among the only songs to top the country, pop, and AC charts.

Rogers' success declined in the 1980s after "Islands in the Stream", although he managed a semi-regular chart presence until 1991. After an eight-year stretch in which he recorded albums but did not issue very many singles, he launched the single "The Greatest" in 1999 off his own label, Dreamcatcher Records. Although it had only modest success, the album's second single, "Buy Me a Rose" (with guest vocals from Music/{{Alison Krauss|And Union Station}} and Billy Dean), returned him to the top of the charts in 2000. None of his other singles matched the success of that song, however, although 2006's ''Water & Bridges'' on Capitol Records gave him a little bit more commercial success.

Rogers is also known for being prolific in the duet field, having cut several duets with Parton, as well as Dottie West, Kim Carnes, and James Ingram. He is also one of the highest-selling male country artists.

In 2013, it was announced that Rogers was being inducted into the Country Music Hall of Fame. For his millions of fans, his induction is considered long overdue.

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!!'''Tropes present:'''

* BadassBeard: Always part of his look.
* BookEnds: In "Coward of the County", the line "Everyone considered him the coward of the county" is found at both ends of the song.
* BreakupBreakout: From The First Edition.
* EarlyInstallmentWeirdness: Most of the First Edition's material was more psychedelic rock, most notably "Just Dropped In (To See What Condition My Condition Was In)".
** Kenny also played bass guitar in the band; he started as a jazz upright bassist before switching to electric in the Fifth Edition.
* TheFilmOfTheSong: "The Gambler" spawned five [[{{MadeForTVMovie}} TV movies]].
* TheGamblingAddict and ProfessionalGambler: One of the leads in "The Gambler".
* HeavyMeta: "Sweet Music Man".
* KnowWhenToFoldEm: "The Gambler" is the TropeNamer.
* MurderBallad: "Ruby, Don't Take Your Love to Town" and "Tomb of the Unknown Love". He also covered Leon Ashley's "Laura (What's He Got That I Ain't Got)", which is written ambiguously enough that it can be about either a murder or a suicide.
* NarratorAllAlong:"Buy Me A Rose". The song is about a man who doesn't pay enough attention to his wife. It's set in third person until the last verse, when it changes to first person for TheReveal.
* ProfessionalGambler: The other lead in "The Gambler".
* [[TheSoCalledCoward The So Called]] [[http://en.wikipedia.org/wiki/Coward_of_the_County Coward Of the County]] (The song provides a quote for that trope's page.)
* Usefulnotes/TheVietnamWar: ''Ruby'', about the return home of a disabled Vietnam vet.
* SpaceWestern: "Planet Texas".
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