The funny thing I noticed about these mishaps is how frequently there is a kernel of humor in the joke. There's the one I heard about a condemned prisoner's last words - "warden, the electric chair isn't plugged in". If you tell this joke a certain way, you are guaranteed a good laugh. But what if I point out that when I first heard this joke, it was about a Polish guy, or a blond? What if it was about someone with a mental disorder? There is a point where a joke simply stops working, but I don't think it's necessarily accurate to say it's an issue with the humor - rather, it's about the audience's discomfort with someone becoming a victim of the joke, and how this discomfort makes it impossible to consider the humor. It's like being served an adult coffee that's been topped off with extra enthusiasm - no matter how much caffeine is in the drink, at some point the alcohol will bring you down.
The problem I have with this comedic style - beyond the offensiveness of certain jokes - is that it requires the audience to take on a disproportionate share of the risk. Think about the implicit agreement in comedy - if the performance is good, the audience will enjoy a few laughs while the comedian builds a reputation. This distribution of rewards suggests that the comedian, who stands to benefit the most from a good performance, should also take on the most risk, just as it should be in any risk-reward consideration. Broadly speaking, this is how comedy works most of the time - the performer and the audience work together toward a goal, then everyone has a share of the rewards. The balance of power shifts the moment a comedian makes a joke at someone's expense. If such a joke flops, the comedian is going to suffer a tiny bit - it's never a nice feeling to get a flat reaction from the audience - but it's possible someone in the crowd will leave with a humiliating memory of the night. On the other hand, if the joke goes well the comedian will earn a big laugh, but it's unlikely anyone put at-risk by the joke will muster more than a defeated chuckle. In this style of comedy, the performer wins big, or loses small; the victim loses big, or breathes a sigh of relief. I would hardly call this a fair allocation of risks given the distribution of potential rewards.
I suppose this is why Mitch Hedberg is my favorite comedian. He operated from a different playbook than his peers - he first separated what you couldn't say from what you could, then he said the funniest of the latter. I looked through this article ranking 275 of his jokes and got the sense that he never made his audience uncomfortable. The remarkable aspect of this observation is that it remains true by today's standards (1). Since he never bothered the elephant in the room, it meant that when his jokes tanked they tanked because they weren't funny at all. It's a subtle difference from when jokes flop because they aren't funny enough, but it makes all the difference. To put it another way, what Mitch Hedberg did was take that old adage - you can say it if it's funny - and elevate it to the next level - he said what was funny. He created something valuable out of nothing more than his mind, which differentiates him in a field that is too often defined by performers stepping on someone else's back to climb to new heights.
It may seem odd at first to waste all this energy just to make this minor distinction. Can't I just take a joke? But my standards have changed, such that I now feel the punch more than the punch line. We live in a system that is inherently incapable of separating creators from takers, but instead of facing the challenge we have clumsily equated the two. When I hear a committed capitalist defend unethical practices - it's profitable if it earns a profit - I realize that something about the original intent was lost in the execution. The simplistic view suggests that if an action brings in a greater return than expense, then the action is profitable, and the action is justified. Too often, however, the equation overlooks the breadth of expense and neglects those who, at the very least, should be made whole after the transaction. Too often, the equation overlooks the importance of everyone having a share of the rewards, for without the promise of shared rewards we become incapable of working together for common goals. The capitalist piles more onto the plate without making the necessary distinction - does the slice come from a shared allocation of a growing pie, or was it taken from a neighbor? All too often, the glittering profit distracts from the suffering left in its wake. We can do it if it's profitable, but for whom? It is a systemic joke told at our expense, and I sense fewer and fewer of us are laughing.
Footnotes
1) I got through the top 33 before I came across a joke that I could see being out of order (the premise is neglectful pet ownership). The next one worth mentioning, #57, makes a reference to gambling addiction, but... well, you can read it. I finished the top 100, and those were the two I thought might make an audience member uncomfortable.