So many. First was when I saw GPT-2 create jokes that were original and kinda funny.

Most recent: I use Claude Code and have a convention where I grant various levels of autonomy during a session. I got bored recently and just let it keep running with an empty issues queue, essentially telling it to do whatever it wanted.

It did a bunch of repo cleanup, then it kept suggesting to end the session, but I just kept giving it autonomy prompts.

It started a creative writing public repo and wrote a bunch of stories, essays, and poems. I did not prompt it, at all, to do that. Some of what it wrote is quite good (IMHO).