There was another question about My Bloody Valentine, which originally had a different scripted ending where Jensen’s character, Tom, dies. They shot the alternate ending too, and that’s the one they kept – which I loved. Jensen said that Phil Sgriccia likes to do that on Supernatural too. Sometimes after they’ve shot a take, he’ll say “Jensen, do something different this time,” and Jensen will just be like, okay, and go for it. It doesn’t work so well with guest actors, who of course don’t realize that the Supernatural set is a bit different than most others.
Phil to guest actor: Okay, do something different this time.
Guest actor: (looking petrified) Um, like what??!By
-From Fangasm’s Jensen Meet & Greet Report, DallasCon 2014
Dean had prided himself on making sure things usually worked out.
Like hustling bars in a pool game, taking on the biggest toughest son of a bitch in the hopes of distracting people enough to slip away, or pumping out just enough of his pheromones to confuse and derail any possible violence. He was good at it, he’d become a master at squeezing just those few extra dollars out of anyone, whether it was a gay at a bar or a customer in a restaurant on one of the few honest jobs he’d ever gotten.
But that wouldn’t do anymore. Sam was starting college in less than two years and Dean had enough student loans to bury a cruise liner in and he hadn’t even finished his degree yet and wouldn’t for some time.