So many to choose from, actually. From Gawker, to TGWTG, to Cracked. A lot of entertainment websites that turned over the years.
I think the first nail in the coffin was when DA admins decided to stop policing the people who use their site like a dumpster for re-re-re-recompressed, ripped-off content. The site immediately started filling up with a completely different culture of lower functioning people. The final nail was when they decided to become facebook for "fandom" instead of a site for digital art.Deviantart, in the early days, was where most of the cool artists hung out, even if there were still fetish loons hanging around. Once tumblr and twitter became popular they all migrated and DA turned into the ghost town of only furries and piss-lovers.
I distinctly remember the article that made me stop. It was something about the harsh realities of being an undercover crack whore and all I could think of was, "how is this in any way shape or form supposed to be funny?" In fact, that's when I began to notice that the site had quietly removed the "humor website" moniker, which was just as well since the site had stopped being funny. I also remember some asshat telling me the site didn't have to be funny when I questioned another article and why there was a distinct lack of jokes.Oh jeez...I forgot Cracked was a thing until I saw the OP, lol.
I used to love their list articles. Yeah they were clickbait-y, but they were also oddly unique and felt like they had some thought put into them.
For example: Top 5 Cobra Commander terror plots that could have worked, and then the article goes on to cite real world examples that tie into those seemingly wacky cartoon plots to show that they could have actually worked.
Stuff like that made for fun reads.
Then I noticed they started drinking from the cup of social justice...never a good sign. They started uploading videos of what looked like beta hipsters sitting in a coffee shop and talking about movies. It was like Seinfeld if Seinfeld was devoid of charm and actual humor...and that sort of became Cracked's content...yikes.