A man of both the arenas and the beaches. 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 Renee Zellweger
- 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)
- Advertised Extra: 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 Reba McEntire'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 co-writer 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 George Strait 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.
- Album Title Drop: "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."
- Broken Streak: Life on a Rock was his first album since his debut not to be certified gold or higher.
- 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.
- The Four Chords of Pop: "Come Over" is a somewhat unusual variation of vi-IV-I-V.
- Genre Shift: From a fairly normal 1990s country singer to a Caribbean-influenced purveyor of songs about island life.
- 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".
- Love Nostalgia Song: "Anything but Mine" recalls a spring break lover, but unlike most other examples, it's in medias res.
- 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".
- Nice Hat: He almost always wears either a cowboy hat or a straw hat.
- Old Man Conversation Song: "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.
- Popcultural Osmosis Failure: 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.
- Prematurely Bald: According to this article, he began balding at age 19. Hence the Nice Hat.
- He actually appears hatless in the "Come Over" video.
- 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 the only thing he released between 1999 and 2012 that didn't hit Top 10.
- Also done with "I'm Alive", a duet with 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.
- 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.
- Something Completely Different: 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.
- 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.