In season 10 of Supernatural, Dean Winchester turns into a demon due to the Mark of Cain and he spends the first few episodes of the season hanging out with Crowley. The two live the party life together, but Crowley knows it’s only a matter of time before bloodlust overwhelms Dean and turns him into a murderer. In the second episode “Reichenbach” the two sit down for a drink. Dean orders for both of them at the bar and says, “Two shots here and he’s got something fancy with your smallest umbrella.” Crowley smiles at Dean in surprise, and when the bartender presents him with something resembling a piña colada, he looks up with one grin on it before continuing the conversation.
This fun little moment was posted by user u/livie3194 on the official Supernatural subreddit with the caption “If this isn’t Crowley’s happiest moment on Supernatural idk what is” and other fans agreed. In a response noting what a great characterizing moment the scene is, u/KurtyVonougat wrote, “It shows [sic] which he actually wanted but didn’t want to be seen ordering himself.” Speaking for Supernatural fans at large, u/TheSkyeIsTheLimit03 commented, “And with that one smile, the rest of the fandom smiled with him.” Hey, if You’re the king of hell must have few reasons to smile – so in this episode he at least has one.