Hey, it's Greg,
First of all having more than one punch for the same setup is a problem worth having. This means you continued to explore even after you found a good punch. Too many comics stop once they’ve found a good punch and I think this is a mistake. Always keep looking for something funnier.
A great example of having multiple punches for the same setup is the Letterman Top 10 Lists. In this case there was one setup and 10 punches. And you can bet they wrote 50 to 100 and pared it down to the best 10. I’m guessing they were picking the ones that were the most negative.
First, let’s review the two patterns of one-liner jokes:
Good to Bad
This is where the setup is about something good, i.e. “I told my brother-in-law, ‘My house is your house.’” Then the punch is about something bad, i.e. “So, he sold it.” This joke goes from good to bad.
Bad to Worse
This is where the setup is about something bad, i.e. “My wife says I’m too nosy?” Then the punch is about something worse, i.e. “Well, that’s what she keeps writing in her diary.” This joke moves from bad to worse.
With that established, I’ll answer the question: the punch with the more negative judgments or consequences is funnier.
I’m not sure if this is always true, but it’s a great guideline because it’s more often true than not. If you have more than one punch, figure out which is the worst.
Setup: “For Father’s Day I took my father out.”
Punch 1: “And left him there.”
Punch 1 is negative in that the comic took his father somewhere and left him to fend for himself.
Punch 2: “With a 45 automatic.”
With Punch 2, the comic killed his father, so that’s more negative than just leaving him on his own, so this should be funnier.
Punch 3: “The goodnight kiss was awkward.”
Punch 3 implies the comic is dating his father and therefore more negative than both Punches 1 and 2. (At least for most people.)
Then again, Punch 3 may cross the hurt line for some audiences, so the job of the comic is to notice the demographics of the audience to determine which punch will get the best laugh.
There are few actual rules in comedy, so this is a guideline subject to comedic interpretation. Rest assured that if you’re always moving toward the more negative, more often than not it will be funnier.
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