I'd stumbled across TUO whilst at uni. Two particular oracularities have stuck with me through the years.
One, I've shamelessly borrowed numerous times:
Q: What is the point of anything?
A: The sharp bit at the end.
(https://internetoracle.org/digest.cgi?N=690)
The supplicant owed the Oracle a picture of a porpoise.
The other was one of the occasions on which the oracle instance broke character.
The supplicant was in what was then still sometimes called Yugoslavia, asking why what was happening there was happening -- a rather bloody and horrific civil war slash genocide.
The oracle's response, paraphrased: I'm just a humble graduate student and really cannot answer your question, but yes this is indeed horrible. Told rather better than I'm recounting it here. The impression of two minds sharing empathy across an anonymous interface stuck with me. It's small example of some of the best that the 'Net can do. (And yes, occurred at the same time that genocidal propaganda was also being disseminated across Usenet.)
Likely some point in the 1992 - 1994 timeframe, most likely 1993, and contained within one of the digests.
(I'll see if I can track it down more precisely.)
But the whole schtick generally: grovel, Oracle, payment, Oracle's backstory (girlfriend, etc.). I guess they're a marker for a fairly small subculture.
Here's to having been there.