- Awesome Music: "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 Heartwarming Moments in tribute to his father and his daughters.
- Broken Base: "Where Were You" is one of his most popular songs, but some critics, most notably Trey Parker and Matt Stone, 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.
- Covered Up: Several instances.
- Many country music fans are unaware that "Mercury Blues" is a pop standard from 1949, having been covered by The Steve Miller Band among others.
- Or that "Summertime Blues" was recorded by several artists, including original singer Eddie Cochran and The Who.
- "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 George Jones 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.
- Similarly, more probably recognize his version of "It Must Be Love" than Don Williams' version.
- Ending Fatigue: He has a tendency to over-write at times:
- "Country Boy" 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 five times at the end.
- First and Foremost: 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 Don Williams'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".
- Misaimed Fandom: Although it's blatantly a Take That! 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.
- Second Verse Curse: The radio edit of "Good Time" cut two verses and most of the solos.
- Sequel Displacement: 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".
- Signature Song: "Don't Rock the Jukebox", "Chattahoochee", "Gone Country", "Where Were You", "It's Five O'Clock Somewhere" to name a few.
- Tear Jerker: "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.
- Unintentional Period Piece: "www.memory" could only have come out during the Internet explosion at the Turn of the Millennium. 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 poor reputation.
- Unintentionally Unsympathetic: 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."
YMMV / Alan Jackson