So Dean takes out his machete, right there within a few steps of a busy street, and holds his hand out to Benny. They shake, then pull each other in for a hug. "Thank you," Dean says. Benny just nods against his shoulder. They pat each other on the back and then pull away. Benny takes a preparatory breath. "Come on, you wimp," he laughs. He lifts his chin to give Dean better access and then, with one swipe of the blade, it's over. Benny falls out of frame as Dean stares in horror.
Look, it's not a bad way to send off the character -- in theory. It brings Benny full circle, from wanting to get out of Purgatory to wanting to get back there. It's just that -- like so much else in the episode -- it depended on stupidity. Sam and Dean had to trap the world's easiest crossroads demon. They had to make a deal with a rogue Reaper without asking him about the consequences. Sam insisted he had to go to Purgatory by himself. Dean had to inexplicably leave the Reaper's side. It's like those experiments you do in high school chemistry class, where you mix a series of chemicals, wait for the precipitate, then mix that with some other chemicals. If you get a step wrong somewhere along the way, then you end up with the wrong result and you fail the test. Except here, they had to get every step wrong to get the right result. And they still failed.
"Dean spent a year in this place?" Bobby wonders back in Purgatory. "Must have been hell on you, not getting him out all that time." Sam studiously avoids looking at him. "You did try," Bobby presses. Sam reminds Bobby about that stupid, totally nonexistent rule they have about not looking for each other because even after 19 episodes he can't just say he was wrong. 19 episodes and zero character advancement. How's that for a season? Bobby takes him to task for it, sort of, and says, "I get the feeling a lot must have happened while I was gone." It certainly could have been harsher, but at least somebody besides Dean said something.
While Sam makes with the sad puppy face, three guys charge at them from the woods. Sam handily dispatches two of them while the third goes after Bobby. With impeccable timing, Benny shows up to grab Bobby's attacker and tears out his throat. How did he find them so quickly? Did he sniff out Sam's Pantene? Also, how funny would it have been if Benny, having lived a relatively upstanding life this time around, completely bypassed Purgatory and went to Heaven? Very funny, that's how funny. Sigh. Bobby advances on Benny with the Demon Knife, but Sam stays his hand. Benny spits out a chunk of monster and looks up at them with a toothy grin. "Why are you here?" Sam asks. "Dean sent me," Benny says. "Not my Dean," Bobby says, still raring to gut the guy who just saved him. "He's a buddy of Dean's," Sam explains. "A good buddy," Benny clarifies. Are there Dean and Benny shippers? I'm asking for a friend.