I think the cause would be better served if RMS would stop calling it "free" software and stop with the speech/beer analogy. As hilarious as the wordplay may be, most people simply don't get it.
The other irony is that GPL is not even free (as in speech) either, it imposes rather strict conditions.
I doubt that he is going for wordplay. Rather, he is trying to convey that it's not the price he is talking about when he says "free", but "freedom". And it's a simple example that makes the distinction and sticks. Maybe he should've called it "Freedom Software"?
Regarding "it imposes rather strict conditions": Yes, it imposes the condition that the user of the software retain their freedoms with respect to the software.
Software freedom is a double-edged sword: to have it, you have to restrict other people's freedom to take it away from you.
I actually do release some code under GPL, but it's when I want those restrictions in order to prevent certain types of commercial usage (and of course when my code uses or is based on GPL code). But I certainly don't consider it to be free in any way except free as in beer.
The GPL is a user-friendly license, not a developer-friendly license. It restricts your ability to restrict the user from doing what they want with the software.
Recall that the GPL started because RMS was a user of a particular type of printer and the printer driver was bad. He was a user of the software yet he couldn't have it fixed (well, he could if the company that wrote the driver did the fix).
I feel like you get the explanation reversed - everyone gets it, but it's just not that funny. Jokes that aren't funny are off-putting, not attractive.
I should have added *sarcasm regarding the funny part.
I have to disagree though, most users have no clue what that means other than it costs them nothing. And many developers simply ignore and violate the terms because they don't understand the restrictions.
it's not even supposed to be a funny joke. It's just an idea, "think free as in speech, not as in bear" is a plain thing to say just explaining which definition of the word is meant. It's not a joke or clever.
The other irony is that GPL is not even free (as in speech) either, it imposes rather strict conditions.