* BlackSheepHit: His biggest hit was the Music/JimmyBuffett duet "It's Five O'Clock Somewhere", which fit Buffett's laid-back, beachy style well but was a bit of a departure for the more twangy and buttoned-down Alan.
* CreatorsOddball: Both of the ''Precious Memories'' albums were covers of Christian hymns and gospel standards, with more stripped-down production. They were both followed by further examples: the first volume was followed by the slick, smooth, mellow ''Like Red on a Rose'' (also his only album not to be produced by Keith Stegall), and the second by ''The Bluegrass Album''.
* NamesTheSame: He waited until 1996 to release "Home", a cut from his debut album, so that it wouldn't get confused with Music/JoeDiffie's 1990 release of the same name.
* ThrowItIn: Jackson began whistling at the end of "Right on the Money", unaware that the tape was still running. He and Keith Stegall both liked the sound and left it in.
* 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]].
* WhatCouldHaveBeen: "It's Alright to Be a Redneck" was supposed to have been the fourth single off ''When Somebody Loves You'', but it was pulled after only a few weeks so that Alan could release "Where Were You" in the wake of 9/11.
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