Many Internet Radio shows do this in terms of sheer vulgarity since there is virtually no censorship; wonder how far it can go; this line says it all: "Oh god they said that Jesus gave it to his mother!"
After The Forking Show (ATFS), a podcast spinoff of a now defunct Australian radio show called The Spoonman, crosses the line in every podcast. One notable, repeated example: Bringing slavery to Australia (both played for laughs and discussed seriously).
The cartoons in The Rejection Collection crossed the line once when they were rejected by The New Yorker, but crossed it a second time when they were funny enough to be published in this book.
Bringing guns into an NBA locker room and threatening a teammate with them? Crossing the line. At a game, pantomiming shooting his teammates as a joke? This trope. Nice job, Gilbert Arenas.
The funnier jokes on Sickipedia. There's a reason why Frankie Boyle and Sickipedia appear to have reached something of a "steal and steal alike" agreement.
Mel Brooks on what he does for a living: "If I cut my finger, that's tragedy. If a man walks into an open sewer and dies, that's comedy!"
Any tragic event will lead to jokes. Immediately. When Too Soon doesn't qualify, this trope usually kicks in.
Sending a gift box containing a stuffed representation of the organism that causes an STD? Tasteless and offensive. Sending a gift box containing five stuffed representations of various STD causing organisms? Hilarious.
This one lists a ton of fictional children's books whose Alliterative Titles use the format "[name]'s [adjective] [disease]". This leads to fun titles like "Bertha's Blossoming Bulimia", "Carol's Colorful Chlamydia", "Dominic's Domineering Dementia", "Hillary's Hilarious HIV", "Lisa's Lovely Lassa Fever", "Prunella's Practically Preventable Prion" and "Sam's Saintly Schizophrenia".
"I'm so happy I bought a hard copy version of this book. If I bought an audiobook, I never would have gotten my money's worth as both of my daughters went deaf from Measles Encephalitis. They now have a great book and a lifelong disability to remind them how much I truly love them!"
This one calls "Benevolent Bubonic Plague" a "gentle, all-natural diet aide", says that the USA only won World War II because FDR got polio instead of the vaccine, and uses some Insane Troll Logic to justify the 1-star rating.
This one is about someone suffering from 30+ "benign" diseases like tuberculosis and malaria. He says that he would've been able to fight them off and become stronger from them if his parents hadn't decided to "weaken" him with vaccines.