I think my first very small directory was built in 1998 or 99. I have had several niche directories mostly in the Science Fiction, Fantasy and Horror categories during the years 2000 - 2005 ish (i no longer remember exactly.) I've used Hyperseek, Gossamer Threads (the free version), early PHPLinkdirectory, early WSNLinks and others. I moved away from web directories until recently when I started re-examining their use. The fun in directories was in the early years when directories were built to help navigate the web. The fun went out of directories when they became mere sources of link pop and PageRank.