* 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 [[{{ItMakesSenseInContext}} 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…
* 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.