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1* CoveredUp: Very rare since he usually writes his own non-parody material too, but it has happened:
2** "Ricky Tidwell's Mama's Gonna Play Football" was originally recorded by Creator/TimWilson.
3** "Stephon the Alternative Lifestyle Reindeer" was originally recorded by Mac [=McAnally=].
4* HarsherInHindsight:
5** "If Shania Was Mine" has a line about hoping that Music/ShaniaTwain will divorce Creator/RobertJohnMuttLange, which they did in 2010.
6** "(Weight's Goin') Up Down, Up Down" ends with Cledus joking about Music/JoeDiffie being mad at him about an earlier line in the song while a heart monitor flatlines. Diffie died of COVID-19 in 2020.
7* SugarWiki/HeartwarmingMoments: "104 Amanda Street", the closing track on his final album, is a heartwarming (and completely serious) ballad dedicated to Cledus' daughter.
8* HilariousInHindsight: "Hell No" laments bad country and bad rap almost a decade before the advent of rap-influenced "bro-country" in 2013.
9* ItsTheSameNowItSucks: One of the main criticisms of the ''Boogity, Boogity'' album (at least according to Allmusic) was that most of his takes on Music/RayStevens' songs were ''too'' close to the originals.
10* UnintentionalPeriodPiece:
11** "Gone Funky" references Music/SaltNPepa, Music/TwoLiveCrew, and Music/SnoopDogg (by his original name, "Snoop Doggy Dogg").
12** "Quit Teasin' Me Ed" refers to Ed [=McMahon's=] appearances for the sweepstakes company American Family Publishers, which went out of business in 1998.
13** "1-900-Sheila": [[UsefulNotes/NineHundredNumber 900 numbers]] went out of vogue in the late 90s.
14** "Christ-Mas" references Tickle Me Elmo.
15** "My Cellmate Thinks I'm Sexy" (Music/KennyChesney's "She Thinks My Tractor's Sexy") is a reference to an incident in 2000 when Kenny and Tim [=McGraw=] got arrested after stealing a Mounted Reserve Deputy's horse.
16** "It's a Great Day to Be a Guy" references ''Series/AllyMcBeal''.
17** "More Beaver" name-drops ''Series/{{Seinfeld}}'', ''Series/HomeImprovement'', and Creator/NickAtNite.
18** "Don't Mess with America" (Music/BrooksAndDunn's "Only in America") could not be anymore obviously tied to [[UsefulNotes/TheWarOnTerror the era right after 9/11]].
19** "I Love NASCAR" (Music/TobyKeith's "I Love This Bar") mentions several NASCAR drivers, including Kyle Petty, Sterling Marlin, Mark Martin, Ken Schrader, Jeff Burton, and Mike Skinner, all of which have since retired from the NASCAR Cup Series (or, in most cases, racing in general). Additionally, many of the sponsors mentioned (including Havoline, Sharpie, Nextel, and [=DuPont=]) are no longer affiliated with NASCAR.
20** "Natalie, Martie, and Emily" (Music/BradPaisley's "Celebrity"), besides being tied to the then-Music/DixieChicks' CreatorKiller moment in 2003, has the line "You are Series/TheWeakestLink, goodbye!", a reference that was dated even then — and only even ''more'' dated when the song reappeared on ''Bipolar and Proud'' a year later.
21** "Waitin' on Obama" (Brad Paisley's "Waitin' on a Woman") references UsefulNotes/BarackObama's election in 2008.
22** "Let's Burn One" centers on the novelty of illegally downloading [=MP3s=] and burning mix [=CDs=], dating it firmly to the peak era of Napster.
23** "Momma's Boy" with John Anderson references Elián González, ''Film/{{Titanic 1997}}'', and audiocassettes. It's also clearly inspired by Scott Rouse's late-90s remixes of Creator/JeffFoxworthy and Creator/BillEngvall standup routines. (Incidentally, Rouse worked with Judd on "Everybody's Free to Get Sunburned".)
24** Many of his parodies came out over a year after the original song, with the gap narrowing considerably over the years. ''Parodyziac!'' zig-zags this, as some of the parodies are of songs from 2010, while the album also includes parodies of Music/LittleBigTown's "Pontoon", which had ''just'' fallen from the charts when the album came out, and Music/EricChurch's "Creepin'", which ''hadn't even peaked yet'' when he spoofed it.
25* ValuesDissonance:
26** It's unlikely that he would have gotten away with "The Change" (Music/NealMcCoy's "For a Change"), which plays a sex change operation for laughs, in the modern day. Especially since Judd himself has [[https://www.youtube.com/watch?v=JaVrchTkXXU since spoken in favor]] of the LGBT+ community.
27** "Illegals" is rife with negative stereotypes of Mexican immigrants. These include rampant use of ElSpanishO, along with jokes about fixing cars, buying too many groceries on welfare, stealing jobs from Americans, and [[ForInconveniencePressOne having to press 2 for Spanish phone options]]. [[ArsonMurderAndJaywalking Also, some of the Spanish subtitles in the music video aren't even translated correctly.]]

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