HOW DID I NOT CATCH THIS UNTIL NOW???
So get this...
We all remember the episode 'It's A Terrible Life' (4. 17, released in 2009), where Sam and Dean were Sam Wesson and Dean Smith (Smith & Wesson is a gun company, so that's a very Winchester-y Easter egg in and of itself) and had boring ol office jobs, right? This episode was also the angel Zachariah's first appearance.
This...
is one of the several spiffy outfits we see Dean in throughout the episode.
Now, the actor who played Zachariah, Kurt Fuller, also had a role in the 2003 Adam Sandler movie, 'Anger Management', in which he was the main character's total bitch of a boss, Frank Head. I recently saw 'Anger Management' for the second time (the first was before I started SPN) and later that night, I was scrolling on here and saw a post that featured a GIF of Dean in this outfit and my jaw immediately hit the floor because I had JUST seen the exact same outfit on Kurt Fuller a few hours prior.
This episode of SPN was released 6 years after 'Anger Management', and it's surely no coincidence since it's the EXACT SAME outfit (to my knowledge) and Kurt Fuller's very first entrance on SPN, so this was almost definitely a deliberate, and quite frankly, genius, Easter egg.
