[[quoteright:300:http://static.tvtropes.org/pmwiki/pub/images/kenny_chesney_251.jpg]]

Highly successful CountryMusic artist. Born in 1968, Chesney began performing in his teenage years, before working at clubs before signing a deal with Capricorn Records in 1993. Capricorn had no experience in the country music field, however; the album received minimal promotion, its singles tanked, and the label closed its Nashville branch.

He then got picked up by BNA Records, a country music division of RCA, and issued his breakthrough album ''All I Need to Know'' in 1995. Although it wasn't until 1997 that he finally scored a Number One hit, most of his BNA singles in this timespan reached Top 10 or better. Kicking his career into high gear, he scored a six-week #1 in 1999 with "Don't Happen Twice." A GreatestHitsAlbum in 2000 produced one of his {{Signature Song}}s, "She Thinks My Tractor's Sexy."

''No Shirt, No Shoes, No Problems'' and ''When the Sun Goes Down'', in 2002 and 2004 respectively, marked a shift in Chesney's sound more towards a combination of eighties rock influences and acoustic songs, quite often about the beach. Along the way, he had the biggest country hit of 2002 with "The Good Stuff," a seven-week chart-topper. This sound, and continued commercial success, followed through the next albums in the batch: ''The Road and the Radio'' in 2005 and ''Just Who I Am: Poets & Pirates'' in 2007. ''Lucky Old Sun'', strangely, produced only two hits, although one was later released as a single from his second Greatest Hits package. His next album, ''Hemingway's Whiskey'', was released late in 2010.

Following the closure of BNA in 2012, Chesney has moved to Creator/ColumbiaRecords' Nashville division.

Chesney was briefly a tabloid target in 2005 after his short-lived marriage to actress Creator/ReneeZellweger.

!!Albums:
* ''In My Wildest Dreams'' (1993)
* ''All I Need to Know'' (1995)
* ''I Will Stand'' (1997)
* ''Everywhere We Go'' (1999)
* ''Greatest Hits'' (2000)
* ''No Shirt, No Shoes, No Problems'' (2002)
* ''All I Want for Christmas Is a Real Good Tan'' (2003)
* ''When the Sun Goes Down'' (2004)
* ''The Road and the Radio'' (2005)
* ''Be as You Are (Songs from an Old Blue Chair)'' (2005)
* ''Live: Live Those Songs Again'' (2006)
* ''Just Who I Am: Poets & Pirates'' (2007)
* ''Lucky Old Sun'' (2008)
* ''Greatest Hits II'' (2009)
* ''Hemingway's Whiskey'' (2010)
* ''Welcome to the Fishbowl'' (2012)
* ''Life on a Rock'' (2013)
* ''The Big Revival'' (2014)

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!!Tropes present:

* AdvertisedExtra: The Wailers on "Everybody Wants to Go to Heaven" — their part is cut out of the radio edit, but they still got chart credit (from the second week at #1 onward, at least).
** Inverted with his duet vocal on RebaMcEntire's "Every Other Weekend", on which he sings a good portion of the song. The song first charted as an album cut credited to both artists. When it was officially released as a single, the radio edit had Skip Ewing singing Kenny's parts (although most stations just played the Chesney version anyway), and it was credited to "Reba [=McEntire=] with Kenny Chesney or Skip Ewing" for one week, then just Reba after that.
** Another inversion came with the GeorgeStrait duet "Shiftwork". It also charted as an album cut with both artists credited, but when it was released as a single, it was credited only to Chesney until about halfway through its chart run.
* AlbumTitleDrop: "Better As A Memory" title drops "Just Who I Am", the album it appears on.
* {{Bowdlerize}}: "Reality" changed the line "Yeah, some days it's a bitch, it's a bummer" to "…it's just bad, it's a bummer."
* ChristmasSongs: ''All I Want for Christmas Is a Real Good Tan'' mixes original songs, traditional covers such as "Silent Night," and country music standards such as "[[WillieNelson Pretty Paper]]," [[{{Alabama}} "Christmas in Dixie"]] and "[[TheOakRidgeBoys Thank God for Kids]]".
* DooWopProgression: The verses of "The Tin Man".
* DualMeaningChorus: Occurs in "There Goes My Life." At first, the young man thinks his life is over; in the second verse, he watches his "life" (his little daughter) walking by; and in the third, he watches her drive off. Also qualifies as an AgeProgressionSong.
* DrowningMySorrows: "Beer in Mexico" is a little more upbeat about this topic than most songs that fit this trope.
* TheFourChordsOfPop: "Come Over" is a somewhat unusual variation of vi-IV-I-V.
* GenreShift: From a fairly normal 1990s country singer to a Caribbean-influenced purveyor of songs about island life.
* GettingCrapPastTheRadar: On "Shiftwork," both he and duet partner GeorgeStrait draw out the I and barely pronounce the F. It even gets furthered by the lyric "A big ol' pile of shiiiiiiiiftwork."
* LoveIsADrug: "You and Tequila".
* LoveNostalgiaSong: "Anything but Mine" recalls a spring break lover, but unlike most other examples, it's ''in medias res''.
* MixedMetaphor: A verse of "Better as a Memory" starts with "Goodbyes are like a roulette wheel" and ends with "Left holding a losing hand". Because, you know, roulette totally involves cards.
* NiceHat: He almost always wears either a cowboy hat or a straw hat.
* OldManConversationSong: "The Good Stuff" is a conversation with an old man at a bar. "Don't Blink" is the narrator's witness of a conversation between a 102-year-old man and a news anchor.
* PopculturalOsmosisFailure: Kenny asked the writers of his 2005 hit "Summertime" if they would change the opening lines, because they mentioned snow cones, and he had no idea what they were.
* PrematurelyBald: According to [[http://leisureblogs.chicagotribune.com/turn_it_up/2009/06/kenny-chesney-the-making-of-a-franchise-in-a-cowboy-hat.html?cid=6a00d8341c58f853ef0115711b9906970c this]] article, he began balding at age 19. Hence the NiceHat.
** He actually appears hatless in the "Come Over" video.
* RereleaseTheSong: Chesney re-recorded his 1994 single "The Tin Man" for his first GreatestHitsAlbum and released the new version in 2001. The re-release has the distinction of being his only single release of the 2000s not to reach Top 10.
** Also done with "I'm Alive", a duet with [[Music/DaveMatthewsBand Dave Matthews]], which originally appeared on the 2008 studio album ''Lucky Old Sun'' and charted at number 55 from unsolicited airplay. It carried over to the 2009 compilation album ''Greatest Hits II'', from which it was officially released as a single, peaking at number 6.
* RhymingWithItself: Subverted in "Me and You," which rhymes "too" and "to."
* SingleMomStripper: The subject of "Dancin' for the Groceries."
* SleevesAreForWimps: One of his trademarks is his sleeveless shirts.
* SomethingCompletelyDifferent: ''Be as You Are (Songs from an Old Blue Chair)'' was a side project that Chesney recorded for the sake of having a whole album of laid-back, acoustic material. It intentionally didn't produce any radio hits.
* TitleOnlyChorus: "Come Over".
* VocalEvolution: In the 1990s, his material was barely discernible from any other young hunk in a cowboy hat, and he had an extremely twangy voice. The twang became gradually less and less evident around ''I Will Stand'', and was almost nonexistant as early as the new songs his first GreatestHitsAlbum. (Just listen to the re-recordings of "The Tin Man" and "Fall in Love" from the latter in comparison to the originals.) By ''When the Sun Goes Down'', his voice also started getting a little softer.

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