* 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.
* CoveredUp: Several instances.
** Many country music fans are unaware that "Mercury Blues" is a pop standard from 1949, having been covered by The Music/SteveMillerBand among others.
** Or that "Summertime Blues" was recorded by several artists, including original singer Music/EddieCochran and Music/TheWho.
** "Song for the Life" was first recorded by its writer, Rodney Crowell, and had been recorded by several other acts.
** "Tall, Tall Trees" was written by Music/GeorgeJones and Roger Miller, both of whom recorded it in the sixties.
** "Little Bitty," written by Tom T. Hall, was originally recorded by him as well.
** His version of "Who's Cheatin' Who" is far more well-known than Charly [=McClain=]'s original.
* [[SugarWiki/AwesomeMusic Crowning Music of Awesome]]: "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).
** Also "Drive (For Daddy Gene)", released right after it, a musical CrowningMomentOfHeartwarming in tribute to his father and his daughters.
* EndingFatigue: He has a tendency to over-write at times:
** On "Country Boy", the song has ''two'' bridges and multiple repetitions of the chorus.
** "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.
** "Long Way to Go" repeats the chorus about four times at the end.
* 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".
* 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.
* PainfulRhyme: Also very present in his work.
** "Where I Come From" contains some real gems: "turnpike"/"midnight," "Ventura"/"finger," "dinner"/"soprano," "Kentucky"/"thunder" and "Tulsa"/"salsa".
** "Ice" and "about" in "Good Time".
** "Ashpalt" and "red dirt" in "Country Boy".
* SecondVerseCurse: The radio edit of "Good Time" cut two verses and most of the solos.
* SignatureSong: "Don't Rock the Jukebox", "Chattahoochee", "Gone Country", "Where Were You", "It's Five O'Clock Somewhere" to name a few.
* TearJerker: "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.
** "Sissy's Song", which he wrote as a tribute to his long-time housekeeper after she died suddenly.