What does a sad cowboy and a supernatural fan have in common?
Both want to put a Winchester in their mouth.
Sad Cowboy Winchester
Explanation
Explain Bear
Alright listen up, chucklenut. This joke is dark. See, a "Winchester" is a type of rifle AND the name of a family on the TV show Supernatural. So the joke is that both a sad cowboy (who might be suicidal) and a Supernatural fan (who idolizes the Winchesters) would want a "Winchester" in their mouth. You probably thought "wow, that's so cool!" when you first read it. Well, you're wrong! Now go think about what you did.