* SugarWiki/AwesomeMusic: Several of his songs. One lesser-known single that's a fan favorite is "Sweet Music Man".
* CoveredUp:
** "Ruby, Don't Take Your Love to Town" was written by Mel Tillis and first released by Johnny Darrell.
** His second Top 40 hit was "Laura (What's He Got That I Ain't Got)", which was previously a #1 by Leon Ashley, a singer who'd fallen into obscurity by that point.
** Don Schlitz released his own version of "The Gambler" shortly before Kenny did.
** His 1988 single "I Don't Call Him Daddy" only got to #86. Five years later, Doug Supernaw took a cover of the song to #1.
** Music/BobSeger was the first artist to release "We've Got Tonight".
** Many of his hits were [[CoverVersion Cover Versions]] of songs first recorded by little-known singer-songwriters. Besides "The Gambler" there was "She Believes in Me" (Steve Gibb), "You Decorated My Life" (Bob Morrison) and "I Don't Need You" (Rick Christian).
** The First Edition's "Just Dropped In (To See What Condition My Condition Was In)", written by CountryMusic songwriting great Mickey Newbury, was first released by Music/JerryLeeLewis, of all people.
** "Through the Years" was first released as an album cut by R&B singer Stevie Woods a few months before the Rogers version came out.
* HeartwarmingInHindsight: "The Gambler" is this [[HarsherInHindsight in a bittersweet kind of way]]. It contains the line "And the best you can hope for is to die in your sleep", and when Rogers eventually passed away in March 2020, it was indeed in his sleep.
* HilariousInHindsight:
** His mother was named Lucille, which later became the title of his BreakoutHit.
** He crooned the line "I don't need children in my old age" in "I Don't Need You". A couple decades later he fathered twin sons at age 66, and lived to their teens.
* NarmCharm: "The Gambler" is extremely cheesey, but that's what makes it enjoyable.
* SampledUp: The chorus of "Islands in the Stream" is perhaps better recognized today as the hook for "Ghetto Superstar" by Pras Michel ft. Ol' Dirty Bastard & Mya, the theme for the 1998 movie ''Film/{{Bulworth}}''.
* SignatureSong: "The Gambler."
* TheWoobie: Tommy from Coward of the County, until [[spoiler: He becomes a WoobieDestroyerOfWorlds]]
* TearJerker: "The Last Ten Years (Superman)" (released in 2008) is a more bittersweet take on a nostalgia song that also pays tribute those we've lost and the victims of tragedy. [[SugarWiki/HeartwarmingMoments Christopher Reeve is mentioned prominently and always referred to as Superman until the fade-out when Kenny says 'gonna miss you, Chris"]]
* UnintentionalPeriodPiece: "The Last Ten Years (Superman)" name-drops a ton of celebrities who died in approximately the decade prior to the song's 2006 release (such names ranging from Creator/DrSeuss to Music/JohnnyCash to Creator/ChristopherReeve), as well as several pop-culture keystones from the TurnOfTheMillennium (such as the dot-com boom and hybrid cars).