For anyone who hasn't seen it and is missing the context, Ally rolled a nat 20 to make Zac say the cowgirl line before cameras started rolling. The timing is all Zac though.
Before the game, Ally rolled a nat 20 on whether or not Zac had to say during the game, "even cowgirls get the blues," and they made it. So Zac did it. (This was explained in Adventuring Party)