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1* SugarWiki/AwesomeMusic:
2** "Where Were You (When the World Stopped Turning)", often considered one of the most truly moving and emotional songs written in response to 9/11. This song won the Grammy for Best Country Song for a ''reason''. It also was named #1 on [=CMT's=] Top 100 lists for both "Television Moments" and "Songs of the Decade" (2000s).
3** Also "Drive (For Daddy Gene)", released right after it, a musical SugarWiki/HeartwarmingMoments in tribute to his father and his daughters.
4* BrokenBase: "Where Were You" is one of his most popular songs, but some critics, most notably Creator/TreyParkerAndMattStone, accused it of cashing in on a (at the time) recent tragedy. Parker ''himself'' also felt these accusations were going to happen, so it was bound to happen anyway.
5* CoveredUp: Several instances.
6** Many country music fans are unaware that "Mercury Blues" is a pop standard from 1949, having been covered by The Music/SteveMillerBand among others.
7** Or that "Summertime Blues" was recorded by several artists, including original singer Music/EddieCochran and Music/TheWho.
8** "Song for the Life" was first recorded by its writer, Rodney Crowell, and had been recorded by several other acts.
9** "Tall, Tall Trees" was written by Music/GeorgeJones and Roger Miller, both of whom recorded it in the sixties.
10** "Little Bitty," written by Music/TomTHall, was originally recorded by him as well.
11** His version of "Who's Cheatin' Who" is far more well-known than Charly [=McClain=]'s original.
12** Similarly, more probably recognize his version of "It Must Be Love" than [[Music/DonWilliams Don Williams']] version.
13* EndingFatigue: He has a tendency to over-write at times:
14** "Country Boy" has ''two'' bridges and multiple repetitions of the chorus.
15** "I Still Like Bologna" has a third verse that doesn't really add anything to the song. Four verses is just a little too much.
16** "Long Way to Go" repeats the chorus five times at the end.
17* FirstAndForemost: Although his cover of "It Must Be Love" got to #1 in 2000, making it one of the few country songs to have more than one chart-topping rendition, it's still thought of almost exclusively as Music/DonWilliams's song. This is likely because the original was already a staple of the classic-country format, while Jackson's take isn't old enough yet to be "classic".
18* HilariousInHindsight: "Gone Country" came out in the mid-90's and yet is more relevant for the country music scene in the 2010's and 2020's with the influx of hip-hop and rap into the genre as it's become more mainstream, and many artists who started in other genres (Darius Rucker, Kelly Clarkson, Michelle Branch, Sheryl Crow, Kid Rock) trying their hand at country music after years away from the pop charts.
19* MisaimedFandom: Although it's blatantly a TakeThat to pop singers who cross over to country, "Gone Country" is often interpreted as a celebration of the genre. Jackson himself has since ran with this.
20* SecondVerseCurse: The radio edit of "Good Time" cut two verses and most of the solos.
21* SequelDisplacement: His first album was ''New Traditional'', a long-forgotten independent release from 1987. Also, his first Arista single was "Blue Blooded Woman", which was quickly forgotten in favor of "Here in the Real World".
22* SignatureSong: "Don't Rock the Jukebox", "Chattahoochee", "Gone Country", "Where Were You", "It's Five O'Clock Somewhere" to name a few.
23* TearJerker:
24** "Where Were You" as mentioned above. There's also "Monday Morning Church", where a man is so upset by his religious wife dying that he can hardly even look at her Bible or talk to God.
25** "Blue Ridge Mountain Song" is likewise a man who found his OneTrueLove, but she got sick and died shortly after they got together.
26** "Sissy's Song", which he wrote as a tribute to his long-time housekeeper after she died suddenly.
27* UnintentionalPeriodPiece: "www.memory" could only have come out during the Internet explosion at the TurnOfTheMillennium. The video goes a step further as it prominently features a woman driving a Chrysler PT Cruiser, a car which was popular at the time but which quickly developed a [[TheAllegedCar poor reputation]].
28* UnintentionallyUnsympathetic: The narrator of "Where I Come From": in the second verse, he badmouths his diner meal because it "ain't like Mama fixed it", and in the third, he blatantly insults a woman who did nothing more egregious than ask him if he had plans for dinner purely because she doesn't (for whatever reason) "sing soprano."

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