Ken Jennings stands his ground, humor-wise, against the attack of the dreaded Twitchy.
When can it work to select an actual well-known dead person as a character in your joking about dying young? Jennings is more of a quiz-show whizz than a comedy writer, and Twitter boxes everyone in with the short format and wide dissemination, so it's hard to judge from this one example, but this is a case of selecting a dead-young person by his political position to demonstrate the truth of the opposite political position, and if the joke-teller isn't someone who has and wants the comic persona of asshole, this is a bad idea.
But I do like the standing of his ground, after he made the decision to joke about the dead man Breitbart. That takes nerve, and that can be funny. Commit to comedy and don't let the first critics scare you into taking it back and apologizing. It's at this point, when the critics step up, that you have a big opportunity to say something especially funny. Prudes will always be pushing you back. They'll always want everyone to stop laughing. A man died! No one should laugh.
But laughing at death is a good move. If you can't laugh at death, life will be nothing but crying, and that would be true idiocy.
Speaking of true idiocy and commitment to comedy, I got an assist in this post from The 3 Stooges! Bonus points to the reader who can guess what question I had, writing the text above, that led me to Google and resolved my question with help from The 3 Stooges....
... who are all dead!
UPDATE: No one wins the bonus. Answer here.