In 1982 a book was published called Truly Tasteless Jokes. Remember, this is pre-Internet: books were still the way to discover jokes. This TV special is about the phenomenon of the book series and the strange history of the author. The show then puts several comedians on screen to read some of the jokes, talk about how tasteless they are, and explain the influence the books had on them. And then ... it branches out into so much more about what you can and can't say as a comedian, cancel culture, and taste in general.
If you're wondering how I came across a one hour TV special when I never watch broadcast TV and don't have a cable subscription: it showed up as a DVD at Toronto Public Library.
To me, the funniest joke in here was from comedian Alison Leiby, who gained some Internet fame for tweeting: "As a woman, I just hope that one day I have as many rights as a gun does." This joke is in the show because of the reaction - which was positive until gun owners twitter-spammed her. Even as a gun owner, you'd have to be pretty humour-deficient to not be at least mildly amused by that - but cancel culture is now a thing, and you can always find people who are offended by anything. Or just want to hurt people for holding an opinion different than their own.
Several of the people in the show remembered reading these books when they were kids, and telling each other the jokes (while keeping it out of sight of their parents and teachers). My childhood slightly pre-dates the publication of the first of these books - but the jokes people told from these books ... they're the exact same ones that floated around my schoolyard as a kid.
There's a significant amount of Canadian content here, as they talked to a Quebecois comedian who was being sued (2015-2019, the show aired in 2018) for a joke he told during his 2012-3 season. I was amused that this included several Quebecois French TV clips (with subtitles, everything else is in English). During filming, the case was still in court: the comedian eventually lost. The joke was by almost any standard "tasteless." As comedy, should it have been a lawsuit-worthy offense? See the show, see what you think.