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Highly successful Country Music 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 Greatest Hits Album in 2000 produced one of his Signature Songs, "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 Columbia Records' Nashville division.

Chesney was briefly a tabloid target in 2005 after his short-lived marriage to actress Renée Zellweger.

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)

Tropes present:

  • Album Title Drop: "Better As A Memory" title drops "Just Who I Am", the album it appears on
  • Christmas Songs: 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 "Pretty Paper," "Christmas in Dixie" and "Thank God for Kids."
  • Doo Wop Progression: The verses of "The Tin Man".
  • Dual-Meaning Chorus: 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 Age Progression Song.
  • Drowning My Sorrows: "Beer in Mexico" is a little more upbeat about this topic than most songs that fit this trope.
  • Getting Crap Past the Radar: On "Shiftwork," both he and duet partner George Strait draw out the I and barely pronounce the F. It even gets furthered by the lyric "A big ol' pile of shiiiiiiiiftwork."
  • Love Is a Drug: "You and Tequila".
  • Mixed Metaphor: 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.
  • New Sound Album: 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.
  • Nice Hat: He always wears either a cowboy hat or a straw hat.
  • Prematurely Bald: According to this article, he began balding at age 19. Hence the Nice Hat.
  • Rerelease the Song: Chesney re-recorded his 1994 single "The Tin Man" for his first Greatest Hits Album 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 Dave Matthews, which originally appeared on 2008 studio album Lucky Old Sun and charted at number 55 from unsolicited airplay. It appeared on his 2009 compilation album Greatest Hits II, from which it was officially released as a single, peaking at number 6.
  • Rhyming with Itself: Subverted in "Me and You," which rhymes "too" and "to."
  • Single Mom Stripper: The subject of "Dancin' for the Groceries."
  • Sleeves Are for Wimps: One of his trademarks is his sleeveless shirts.
  • Title-Only Chorus: "Come Over".
  • Vocal Evolution: 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 Greatest Hits Album. (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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