I don’t get the DCs and “success/fail” in this context, can someone explain? Where would a 5 be a success and 20 be a failure?

The DC to convince the hangman is 5, the DC to convince the head guy is 20. DC stands for Difficulty Check and it is the number you have to pass or meet on your roll + bonuses.

So is the joke that the PC convinced the hangman (who only needed a 5), hence the “success”, but failed to convince the leader (who needed a 20), hence the confused guy reading “failure”?

I didn’t know that the second guy was supposed to be the leader, that would’ve made more sense. Thanks

Makes sense if you’ve seen the movie

Which is…?

a collection of still images played at a constant framerate and paired with audio matching what is shown, usually for entertainment purposes

Thank you for elaborating, no notes. I am now perfectly at ease with the current state of affairs.