As for bizarre broadcasts in SW history, my vote for #1 goes to Radio Uganda. IIRC, in the summer - 1980 - following the deposition of Idi Amin, the nightly NA Service from RU began to soften up and air more Western-friendly programming. This was a nightly broadcast from 0300-0400z (?) near the top of the 19M band (15350?), from the relatively new 250kW Soroti plant. This transmitter put massive signals into NA, but as the inmates seemed to be running the asylum, it also put massive spurs all across the band (and beyond) due to extreme over-modulation.
The programming was exceptionally queer. After a brief segment of Ugandan news, an album was tracked, and this generally consisted of very distorted mx from the Pointer Sisters, James Brown, or the Bee Gees, all of whom were heavy in the nightly album rotation. They seemed to have a fondness for the "Saturday Night Fever" soundtrack, and I also seem to recall that the musical fare for one show was Los Bravos "Black Is Black" repeated over and over again for greater than 40 minutes.
It was a nightly train wreck, and I wish that the logbook from those years hadn't been destroyed in a flood.
In all fairness to RU, they did get it right on one night that I know of. Towards the end of the summer, a 5 song set of East African mx was aired; signal and modulation quality was excellent, and I was able to get a nice cassette recording of the show. What I heard here immediately sparked my interest in African mx, and was a turning point in my musical tastes.