in what show dose dean and sam try out a boreing office day job?

4x17 "It's a terrible life"..Dean is a corporate man who enjoys health drinks and listens to news radio vs. rock stations. He works at a company called Sandover Bridge & Iron Company alongside Sammy who is in Tech Support..

Dean & Sam weren't "trying" out the dayjob....they were set up by Zachariah to test Dean. I loved the play of their last names to separate them as relatives..."Smith & Wesson" vs.Winchester.

its a terrible life