At the hotel, Sam gets a visit from Ruby who tells him that 34 Seals have already been broken, so Lilith is more than halfway to Lucifer walking the Earth. Ruby says he has to kill Lilith, but he has issues with murdering a little girl.

That night, the boys go to see the Incredibly Jay try the Execution, in which he has 60 seconds to escape a noose. He gets out, but at the same time, Jeb the Douche Bag is magically hanged by a rope. Dean is impressed by the trick, by Sam suspects real magic.

The aging Jay makes the boys reflect on their own futures, and Sam is very wary of dying young. He worries that the fight against evil will keep going on, and he and Dean will still be hunting into their old age like Bobby, unless they die before they get that far. For a wacky episode about douche bags, the emotional core of this episode is pretty sad.

The Winchesters bust in on Jay and interrogate whether he’s using real magic. Jay has no idea what they’re talking about, so they tie him up and decide on a plan. Jay, being a skilled magician, slips out of the rope and escapes. He calls the cops and has Sam and Dean arrested for kidnaping.

That night, Jay does the Table of Death again, only this time it’s his best friend Charlie who is killed. Jay decides to drop the charges and ask the Winchesters for help, so the two go to investigate the third old magician, Vernon.

While the boys tear apart his hotel room, Vernon tells Jay the headlining gig is his, but Jay refuses to take it because he assumes Vernon killed Charlie. However, they’re both stunned when a 28-year-old version of Charlie shows up.

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