In the NY Times piece, the Gray Lady tries to explain the phenomenon. Some reasons for its enduring popularity are obvious. Florida is, after all, the third largest state by population; hence, there's a higher probability that some of those people will be very strange (or get themselves into strange situations).
Florida is also a bizarre mix of cultures of transplants from other states and countries (see our "10 States of Florida" map), so it's hard to find a central defining characterization of the state's culture other than simply "weird."
As a side note about the particulars of Florida Man, long before it became a meme, New Times used the headline format "Florida Man Does ..." to indicate to our mostly Miami-based audience that the story took place in Florida but not Miami, which may very well be the reason other local news outlets used the headline format well before it became a meme too.
But missing from Times' take and so many others on the WTF Florida phenom is an important piece of the puzzle. Ironically, one of the things that may be contributing to Florida being shamed so often in the national media is something all Floridians should be proud of.
The terms "progressive" and "model for the rest of the nation" don't often appear in sentences with "Florida," but that's exactly how people view the state's open-records laws, AKA the Government in the Sunshine Act.
Since 1909, Florida has had a proud tradition that all government business is public business and therefore should be available to the public. That means all records, including photos and videos, produced by a public agency are easily accessible with a few narrow and obvious exceptions. Public officials are also required to open all of their meetings — even unofficial ones — to the public.
It's the reason why Miami-Dade County Commissioner Xavier Suarez had to file a public notice to talk to his own son, City of Miami Commissioner Francis Suarez, earlier this month because the two planned to discuss public transit issues. It's why former Gov. Charlie Crist had to invite a journalist to his 2008 wedding. On a more serious note, these are the laws that allow journalists and concerned citizens to uncover examples of corruption, conflicts of interest, and abuse.
When a painfully blunt job listing for a reporter listed by the Sarasota Herald-Tribune went viral in 2011, it stated "for those unaware of Florida’s reputation, it’s arguably the best news state in the country and not just because of the great public records laws."
These laws are probably some of the most sacred in Florida government. Even when Republicans took control of the state government in the early 2000s after generations of Democrat dominance, they didn't touch them. Even when legislators pass laws that limit information from the public, those laws automatically "sunset" within five years if the legislature doesn't reauthorize them.
However, those same laws are also the reason your mugshot appears online days after your arrest, and those laws make it incredibly easy for journalists to write about weird Florida news stories.
You'll notice something when you read so many "Weird Florida" news stories. They almost always include the phrase "according to the arrest report."
As journalists, all we have to do in most cases is call the police department and ask for an arrest report, and the cops are required to give it to us. Nowadays a lot of cops simply email the reports, and some departments even post arrest records online. Some of the more dedicated weird-Florida-news reporters go through batches of arrest reports at a time.
Once you have the report, you pretty much have something to base a story (though always keep in mind that when you see the words "according to arrest report" absent other sourcing, you are just reading the police's version of events).
The process isn't quite as easy in many other states.
Say a journalist elsewhere gets a tip that a man in a dog costume was caught making love to a Hello Kitty doll in a mall bathroom. Here in Florida, we could just call the police and say something like, "Heard there was an arrest at the mall yesterday. Can we get the report?" For journalists in many other states, it's not that easy. They might not be able to get the arrest report or must wait a while before police release it. They might be able to get some information, but without other evidence, they really don't have much for a story — and digging further might take more time than it's worth.
Now combine that with the fact Florida is such a large, weird state and the fact many media outlets know that a particularly weird news story might be a ticket to viral gold (and tons and tons of page views), and you begin to understand why Florida has a reputation for weird crimes. There's probably some ass-backward weirdness going on in, say, Alabama that probably makes Florida look like bizarre-criminal amateur hour, but without those factors, "Alabama Man" isn't gonna catch on.
So perhaps the next time you read a weird-Florida-news story, don't ask why Florida is so weird; ask why you're not hearing about the weirdness in other states. It might have something to do with their lack of open government.