I'm not sure that using C was the craziest thing about how we did things. Nobody really had an idea how to structure a web app, so it was more or less a dozen or so CGIs which read/wrote to flat files through custom-written dbm clone (woo, NoSQL in '96!). Lots of unsophisticated string munging.
Maybe if we'd had some better abstractions, it wouldn't have been as painful, but C code written to do a lot of ad hoc string cobbling is, in fact, a little crazy.
Despite this, the product pretty much worked and actually had a few hundred customers and a future.
(We even got looked at by Yahoo, but they bought some outfit named Viaweb instead.)