Prompted by this post by @shanselman..
Circa 2000 (aka Y2K): I was using classic ASP, VB6, COM, T-SQL, MSMQ. The apps I worked on that year touched on email marketing, and then electronic document filing. I was the alternate/backup DBA on the e-filing app. It was all waterfall, n-tier design, logical layers were also physical layers (UI, Biz/Data, and SQL were each on their own machines).
The year before (1999), I had been working on Retail Branch reporting for then Bank One. It was based on VB6, COM, Sybase, and generated Excel reports. It required some math skill to retro-fit the previous reports since the old business rules and algorithms were “lost”. The local office was on a vault property; and the Retail Management Dpt office was in downtown Dallas, which I got to visit. A lot.