* His and Music/CarrieUnderwood's "Obamacare By Morning" song at the 2013 CMA Awards. Especially the lead-up involving a TakeThat to Music/MileyCyrus.
** Later, at the same show, he "accidentally" sends Music/KeithUrban a sext, instead of sending it to his wife Kimberly Williams-Paisley.
* "I'm Still A Guy" is just one big FunnyMoment, especially if you know the story behind its being written.
* In the otherwise mostly-serious "Letter to Me", about what he would put in a letter to his past self:
-->And when you get a date with Bridget, make sure the tank is full\\
On second thought, forget it, that one turns out kinda cool…
* "Don't you think it's time for me to end this song? ({{beat}}) …Me neither!"
* 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.
** 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/HootieAndTheBlowfish}} Darius Rucker]] laughing his head off.
* 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".
** 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."
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