One Sunday in 1987, two Chicago TV broadcasts were hijacked by someone with a Max Headroom mask, a voice modulator, and an odd sense of humour. He was never caught.

There have been a few significant TV signal intrusions – including one notable 1986 incident in which an HBO satellite signal was hijacked in order to protest rising cable prices – but the Max Headroom intrusion has to be one of the most… unique, I guess?
The first phase was minor: 28 seconds of an evening news broadcast was replaced with a masked figure silently bopping back and forth while a corrugated iron background rotated behind him. (Max Headroom, if you’re not familiar, was a weird stuttering character in an 80s TV show; he was supposed to be a computer AI, although he was played by a man in makeup.) It was a simple signal hijacking: you broadcast your own signal with more power than the actual feed, and you take over the airwaves for a time.
During an episode of Doctor Who on a different channel two hours later, the hijacker returned. And he returned with dialogue and props. He held up a can of Pepsi, flipped off the camera with a dildo, sung a line from a Temptations song, hummed an old animated TV show theme, and exposed his butt so that a lady could hit it with a flyswatter. You can watch the whole thing here:
No-one ever caught the hijacker – his identity and that of his female accomplice remain a mystery to this day. The incident has entered hacker folklore and remains one of the most bizarre and amusing signal intrusions in history.