The singer typed in dozens of sentences into the Mac program, which then randomly selected words, "slamming" them into each other to create lyrics of its own, which Bowie used as a source of inspiration.
He was also one of the first artists to release an "internet-only" single. Telling Lies was downloaded by more than 300,000 people before later being sold as a physical single.
Bowie also took part in 1999's Netaid charity concert, which was streamed on the web to more than two million people, external, a record for its time.
In 2004, he sponsored an online contest for fans to create new "mashes" of his music, but as the years went by he became a more remote presence.
"When he had talked to us, he came across as very caring and compassionate - he could be very fatherly, especially with the younger visitors," says Mr Carrington.
"But about seven or eight years ago, although you could still log into BowieNet, there didn't seem to be many updates, and we were wondering what was happening.
"It was a shame."
In 2006, Bowie's ISP business was quietly retired, but it was not until 2012 that his Facebook page confirmed what many already knew.
"BowieNet, as we have known it, is kaput!" it said, external.