Bad headlines from old newspapers
I went to college for journalism. Thankfully the print industry crashed while I was in college and most of us never even pursued becoming a part of it and went on to do other things. Here's a fun tip about education: It doesn't really matter what you went to school for, most jobs will take you if you just have a degree in anything other than dance and art.
While I was in college though I actually genuinely enjoyed what i was studying. One of my professors would routinely include examples of bad headlines that should be caught by editors and we were in a time of spell-checkers being a relatively new thing but even with spell-checkers there are things that will get past it.
I keep an eye out for these sorts of headlines and they continue to exist today - more frequently actually because there is so much production of articles in the news cycle these days - but I prefer to focus on newspapers because those were the days that once it went to print, it was all over... there was no chance for a quick edit to a digital article.

src
This was something my professor called "talking down" or "infantiling the audience" even though the latter isn't even a word. We knew what he meant. While there are likely many times more headlines like this these days when news centers have to punch out dozens of articles a day to survive, this is just stupid. Of course sadness is associated with depression you donut.

Some of these are so stupid that they seem like Onion articles but nope, these were genuine news articles published in real newspapers that people were employed at for actual money. If any of us had submitted such an article just for our low-circulation school newspaper we would be reprimanded.

src
This is a different example and it comes from using older software that would provide placeholders for images that would later be filled. The author of the two articles are not to blame for this, the editor is. While that is a wonderful and cute picture of a dog, it is in the wrong place. Why they are putting an article about a cute dog next to an article about a sex offender is pretty bad in the first place, but this is yet another mistake that would have gotten us reprimanded and we weren't even being paid.

src
This one is so bad that it wouldn't surprise me if this was intentionally put in there by a disgruntled unpaid intern, which was a very common position to have in the 90's as newspapers slowly died. The dude was probably in a "fuck it" attitude after being bullied by paid staffers who were also getting fired soon and just pushed it through to print. If that is the case I hope that JAL Jayasinghe framed this, because it is gold.

src
This is one of my favorite ones and while this example didn't exist while I was in college, my professor would frequently show us examples about how as an editor, you can NEVER depend on the software to check things for you. You need to read, carefully, with your own eyes and the person in charge of this newspaper clearly did not. There is no reason why any software other than maybe AI these days, would ever find and issue with this headline but to a reader, this is obviously a big mistake. The fact that this wasn't detected suggests the obvious and that is that the editors didn't even read it before sending it out to print. I hope this is framed somewhere because it's amazing. I don't know if Julia has a sense of humor, but I am sure the newspaper was forced to issue an apology.
It was a different time, the days of print media. Today we are bombarded with so many stories day in and day out that I regularly find many mistakes in both headline and the articles themselves on so called "professional" news sites. I don't think they even care anymore though. The idea is to get as many eyes on something as possible and sometimes the misspelling of something can actually get more people to see something than otherwise would. Other times it is sheer laziness because most news these days are trash.
There was a time though when papers actually had to be good in order to compete and remain viable in a crowded and very competitive business landscape. I miss those days. I miss newspapers. I rarely even see one for sale anymore and that is a shame. I think it will become a relic of the past kind of like when you see a grandmother writing a check at the grocery store. Kids these days probably don't even know what that is.