This is one of my all time favorite episodes of the show. There are several factors why. I just happen to like stage magic, magicians and I thought it was about time that the show did an episode like this. Likewise, the vulgarities of aging are pretty obvious fodder for horror and this episode script tries Jay's story into the Winchester story well with it feeling entirely organic and about time this sort of thing was addressed. But mostly it because of two things. First, Barry Bostwick (Jay) and to a lesser extent Michael Rubenstein (Weston) (Young Charlie) give two of the very best one off performances in the show. Bostwick captures the melancholy and regret of Jay grappling with his age and then the choices he was forced to make. Rubenstein plays the affection for Jay and the mad trickster of Charlie fully. The chemistry between them is just great. I almost wish that the characters could be revisited because of how good these two were.
Second this is episode is one of the most overtly homosocial and/or homoerotic episodes in the entire series. It's not just the Chief-through yes that is hysterical and adds to ever growing amount of queer bait with Dean. But the bond Jay and Charlie shared is clearly stronger than mere friendship. On Charlie's end he seems particularly devoted and it almost plays out like a Hays Code era gay villain, which is entirely correct given the general vibe of the episode.
There is a weird emotional power to this episode that crops up because of the various tonalities. It vaguely reminds me-SOMEHOW!-of a queer and B flick version of The Illusionist (2010, animated). That is just wonderful.