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1* His and Music/CarrieUnderwood's "Obamacare By Morning" song at the 2013 CMA Awards. Especially the lead-up involving a TakeThat to Music/MileyCyrus.
2** Later, at the same show, he "accidentally" sends Music/KeithUrban a sext, instead of sending it to his wife Creator/KimberlyWilliamsPaisley.
3* "I'm Still A Guy" is just one big SugarWiki/{{Funny Moment|s}}, especially if you know the story behind its being written.
4* In the otherwise mostly-serious "Letter to Me", about what he would put in a letter to his past self:
5-->And when you get a date with Bridget, make sure the tank is full\
6On second thought, forget it, that one turns out kinda cool…
7* "Don't you think it's time for me to end this song? ({{beat}}) …Me neither!"
8* Paisley's third #1 hit (after "He Didn't Have to Be" and "We Danced"), "The Fishing Song." The narrator's wife warns him that if he wastes yet another day fishing, she'll be gone when he gets home. Considering that the alternate title of the song is [[ForegoneConclusion "I'm Gonna Miss Her,"]] it looks like [[ScrewYourUltimatum it didn't work.]]
9** The music video features faux-serious fishing commentary from [[Series/SportsCenter Dan Patrick]], and a parody [[Series/TheJerrySpringerShow Jerry Springer]] segment.
10* His bit during the opening segment of the 2014 CMA Awards on the P.P.T.S.D.[[note]]Postpartum Taylor Swift Disorder[[/note]] that Nashville was going through due to Music/TaylorSwift moving to UsefulNotes/NewYorkCity.
11** His referring to the fact that the 2014 [=CMAs=] took the time-slot that ''Series/{{Blackish}}'' airs in. He then called it "[[{{SelfDeprecation}} White-ish]]", which was [[{{GilliganCut}} immediately followed by the camera switching to]] a ReactionShot of Music/DariusRucker laughing his head off.
12* His appearance on ''Radio/APrairieHomeCompanion'', featuring a song on the geology of the Ohio River and the Appalachians. It was [[RuleOfFunny supposedly]] planned for a release on the album "Your Substratum Makes My Lava Flow."
13* The music video for "Southern Comfort Zone" lists things involved in making it at the beginning and end. It includes "a tractor," "6 jackets," and "one very friendly Maasai giraffe".
14** The beginning opens up on what appears to be a farm. Then an elephant wanders on screen. Bonus points for pairing it with the word "shocking."
15* "Ticks", a song about picking up someone in a bar and taking them for a walk in the woods...and then having to [[UnusualEuphemism check them for ticks.]]
16* The music video for "Online", starring Creator/JasonAlexander as the protagonist BasementDweller, Creator/WilliamShatner and Creator/EstelleHarris as his parents, and [[Series/TheBradyBunch Maureen McCormick]] as the GirlNextDoor. Particular moments include jokes about Shatner's music career, visions of the [[{{Gonk}} "hot girls"]] that Alexander's character is chatting with online, and Alexander playing the guitar in concert with Music/TaylorSwift and [[Series/AmericanIdol Kellie Pickler]] as his backup dancers.

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