I'll start :-)

Yesterday on CH 16: "Moorings Road Town, Moorings Road Town, this is KNOT WORKING!!"
(no response)
"Moorings Road Town, Moorings Road Town, this is KNOT WORKING!!" (with increasing exasperation)
(no response)

(brief pause)

"My air conditioning is NOT WORKING!!!" (yelled into the mike)

Several years ago in BVI, there was an active MAYDAY going on, the USCG was communicating with a sinking vessel (good conditions, no big winds or waves, sinking boat next to JVD close to shore).

Two ladies on two boats were on VHF 16 talking about which restaurant to head ashore to in the evening. The exasperated CG radio officer stated "This is the USCG San Juan and this is the emergency frequency. SILENCE MAYDAY". The last 2 word are the official terminology for "we're using this channel for emergency communications and if you're not part of it, then SHUT UP and stop transmitting.

Immediately, one of the ladies piped up and stated. "We were here first!"

To that, the USCG replied "What is your name and the name of your vessel?". That worked, as no response was forthcoming.

I think after the charter briefing there should be a written test. The Moorings tells you many times that the dockmaster monitors channel 12 yet people call on 16 over and over. They hand you a printed sheet at check in with every phone number including the assistance numbers if something is broke.
The real problem is people are chartering and allowed to charter who have little to know experience with larger boats and boat systems.
There are charters out there who are afraid to anchor which is a basic skill and a safety item. I had a boat frantically waiving at me at the dogs once. I tried to hail on 16 with no answer. Came along side and they said they had lost power. I told them to drop anchor. They said they could not as they had lost their engine. Told them to drop it manually and they asked if that was possible. Sent one of our guys over to drop it. They then sheepishly admitted the engine issue might be because they ran over a mooring ball. Sure enough they had line and the ball tangled in their prop.
Another time also at the dogs we were getting ready for a night dive waiting for the sun to set. A boat pulls up to the other mooring ball and grabs it. They then ask us if this is Marina Key! We explain they are a bit off course and they say it’s because their chart plotter has failed. I go over and check they have the breaker on and tell them to try again. He punches the power button quickly and nothing happens. I tell him to press and hold it. Magically it lights up!
Knot Working is the actual name of a boat in the Moorings fleet. I kind of like it!

O
M
G

More please. This is freakin hilarious!

Yes, "Knot Working" is a power cat if memory serves.

It has all the makings of a "Who's on first" comedy skit.

Years ago, on our first charter, we were sitting in the cockpit listening to 'traffic' and heard '(some boat), (some boat), this is Cookie Monster."

After hearing other boats asking for various kinds of help we started riffing on the plight of Cookie Monster, postulating on all the different kinds of trouble they could be in.

It was getting silly and then someone offered "Mayday, Mayday, this is Cookie Monster. We've run aground on Fraggle Rock!"

We were in that zone where once you start laughing, you can't stop - even past the point where it should be over - and we were in tears. We reference this to this day, probably almost 40 years later.

Heard one time on channel 16, "Passing Wind calling the Bitter End".

Marina Cay is hard to find. I saw a guy hop out of his dinghy on Great Camanoe with a bag of garbage and very determinedly walk around the marina looking in every corner. Finally he approached a group of us and asked where the dumpster was. He thought he was on Marina Cay!

Oh my - Great Camanoe is easily confused for Marina Cay...

These are great, thanks for the thread, OP!

So not personally heard by myself but cracks me up whenever I think about funny VHF calls, not sure if they hailed the CG or Tow boat but either way these guys boat breaks down out on the water at night.....when asked for their location they said something to the effect, "we are just off ______ (land bearing) ...we're in the moon beam, you can't miss us!"

Ok, here's two separate things we heard on VHF on charter boats back to their mother base "the Moorings":

-- "Can you send a repair boat out? We're having problems with our stereo."

-- "Heh Moorings base. This is _____. We're having a hard time getting that 'sail thing' to go up the pole." - pause - Mooring responds > "We probably ought to get you a captain to go out with you on that boat." - longer pause - The boat replies: "Yeah, that might be a good idea!"

Late at night at anchor in Green Bay, Wisconsin...unnamed boat with a clearly inebriated caller asked the CG to officiate a dispute about a Scrabble word. CG was NOT amused.

Different VHF but a United flight going into RNO received a complex clearance from a fast speaking female controller. United asked her to repeat the clearance to which she replied, “United, you need to listen up!” A pause and the United pilot said, “Were we married once”?

>Were we married once”?<<
Heard it was the famous “Kennedy Steve” at KJFK