A CountryMusic artist known for his traditional, no-frills songwriting, down-home charm and humility... and shelf full of awards.

Alan Eugene Jackson was born October 17, 1958 in Newnan, Georgia. started out unassumingly enough in 1989 on Arista Records, which at the time had virtually no experience in the country music business. He was even working with Keith Stegall, a former solo singer with no production experience. Although his debut single "Blue Blooded Woman" flopped, he first cracked the Top 40 in 1990 with "Here in the Real World" and enjoyed nearly 20 years of hits. Coinciding with his departure from Arista, he provided duet vocals on ZacBrownBand's "As She's Walking Away". With his fortunes fading at radio in TheNewTens, Jackson has moved to his own label, Alan's Country Records, with distribution by EMI.

His accolades include twenty-five Number One singles, fourteen Academy of Country Music awards, twelve Country Music Association awards and a Grammy.

Jackson also co-wrote singles for FaithHill ("I Can't Do That Anymore"), RandyTravis ("I'd Surrender All", "Better Class of Losers"), Clay Walker ("If I Could Make a Living") and ChelyWright ("Til I Was Loved by You"). His nephew Adam Wright, and Adam's wife, Shannon, record on Alan's label as The Wrights, and they have occasionally collaborated with him.

!!Tropes present:

* AlbumTitleDrop: ''A Lot About Livin' (And a Little 'bout Love)'' is named for a line in "Chattahoochee".
* AntiChristmasSong: "Please Daddy Don't Get Drunk This Christmas".
* {{Bowdlerize}}: "I'll Try" opens with the line "Here we are, talkin' bout forever / Both know damn well it's not easy together". Even though it wasn't his first time swearing in song, the "damn" became a "too" on the radio edit.
* ChristmasSongs: He has done two albums of Christmas music.
* CoverAlbum: ''Under the Influence.''
* DistinctDoubleAlbum: ''Greatest Hits II... and Some Other Stuff''. The "Other Stuff" was a bonus disc comprising eight cuts from previous albums that had never been released as singles.
* DooWopProgression: "Remember When"
* EverythingIsAnInstrument: Alan "plays" a hammer striking an anvil on "Hard Hat and a Hammer."
* HeavyMeta: Besides the three-minute example listed below, this is also present in "The Talkin' Song Repair Blues," where songwriting is compared to fixing a car.
* ImAManICantHelpIt: In "Work in Progress", he admits to being forgetful and careless, but pleads with her to be patient because he's a work in progress.
* IWantMyBelovedToBeHappy: "So You Don't Have to Love Me Anymore".
* ItWillNeverCatchOn: According to the liner notes of his first GreatestHitsAlbum, Jackson thought that "Chattahoochee" was too dependent on a localized reference (the Chattahoochee River on the Alabama/Georgia border) to become a hit. His worries were for naught, as it was the biggest country song of 1993.
* LyricalDissonance:
** "I'll Go On Loving You" is awfully melancholy for a song about how he will still love his woman after he's had sex with her. Really, [[SuspiciouslySimilarSong it sounds like a lot like "Suicide Is Painless"]].
** In the other direction, "Don't Rock the Jukebox" is pretty upbeat for a song about a guy trying to convince people to not play upbeat songs so he can commiserate.
* LyricSwap:
** "Where I Come From" can't seem to make up its mind whether the chorus is referring to pickin' or sittin', and whether it's on the front or back porch.
** Similarly, the third chorus of "I Still Like Bologna" changes "the sound of a whippoorwill down a country road" to "…a Chevelle headin' down a gravel road".
** The last iteration of "Country Boy"'s chorus changes "Up city streets, down country roads" to "winding roads".
* LoggingOntoTheFourthWall: Jackson created an "alanjacksonmemory.com" website as a tie-in to his 2000 single "www.memory".
* LyricalShoehorn: Pretty much all of the last two verses of "Where I Come From", which are composed of awkward phrasings and rhymes that barely make sense (for instance, "use my finger" is how he describes hitchhiking).
* MidwordRhyme: The first chorus to "Like Red on a Rose":
-->And I love you like only little children love pennies
-->And I love you 'cause I know that I can't do any—
-->—thing wrong
* NiceHat: He always wears a cowboy hat.
* RecordProducer: He's worked with Keith Stegall on all but one album (the aforementioned ''Like Red on a Rose'', produced by bluegrass queen [[Music/AlisonKraussAndUnionStation Alison Krauss]]). His first two were co-produced by Scott Hendricks (as was one song on the third), and his 2013 bluegrass album had his nephew Adam Wright as co-producer.
* RereleaseTheSong: Alan wanted to release "Home" off his first album, but decided against it because there was another song out that had the same title. The original recording was finally released as a single from a GreatestHitsAlbum in 1996. Later on, he re-recorded "A Woman's Love", originally from 1998's ''High Mileage'', and released the re-recording from 2007's ''Like Red on a Rose''.
* RepurposedPopSong: His version of "Mercury Blues" was rewritten to be about Ford trucks and used in mid-nineties Ford commercials.
* SelfBackingVocalist: He often does his own backing vocals. And it shows.
* SignatureStyle: He tends to use the same musicians from album to album, helping to define his ThreeChordsAndTheTruth style even more. Moreso on his early albums, he often let the musicians do a lot of solos.
* SomethingBlues: "Mercury Blues," "Summertime Blues," "The Talkin' Song Repair Blues".
* SomethingCompletelyDifferent: Alan tried this twice in 2006, releasing a gospel album and a more adult contemporary-sounding album within a few months. The gospel album was only a side project, and the latter (''Like Red on a Rose'') was met with mixed reviews in comparison to his previous work, sold poorly, and only produced two singles. He returned to his traditional sound starting with ''Good Time''.
* TheSomethingSong: "Three Minute Positive Not-Too-Country Up-Tempo Love Song". Also an example of AntiLoveSong, RunningTimeInTheTitle, HeavyMeta, LongTitle and ExactlyWhatItSaysOnTheTin.
* TakeThat: "Murder on Music Row," his duet with GeorgeStrait, is a big TakeThat to the crossover-happy country music climate of the early aughties.
* TheCoverChangesTheGender: The original version of "Who's Cheatin' Who" was from a female perspective. Jackson, obviously, changed it to a male's.
* ThirteenIsUnlucky: Lampshaded on the back of his ''Who I Am'' album. The track numbers skip from 12 to 14, with a note saying "That's right, folks, I am just a bit superstitious. -- AJ".
* ThreeChordsAndTheTruth: Jackson is clearly influenced by the no-frills storytelling songs from the likes of MerleHaggard.
* TitleOnlyChorus: "I'll Go On Loving You".
* VisualPun: The video for "She's Got the Rhythm (And I Got the Blues)", upon reaching the line "She spells out 'regret' in perfect time", has a woman literally moving her hands in the direction of the letters R-E-G-R-E-T as they appear onscreen.
* VocalEvolution: His voice has gotten a little deeper with time. As of "Long Way to Go" (his first release for EMI), he also seems to have lost a lot of range.
* WatchingTheSunset: Mentioned in "Where Were You (When the World Stopped Turning)".
* WhatWouldXDo: From "It's Five O'Clock Somewhere":
-->''I could pay off my tab, pour myself in a cab, \\
An' be back to work before two.\\
At a moment like this, I can't help but wonder,\\
What would Music/JimmyBuffett do?''
** And then Jimmy answers