On October 4, 1993, Advertising Age (Ad Age) inaugurated “INTERACTIVE Media & Marketing” (a section henceforth referred to as INTERACTIVE), a new department in the popular and influential trade journal. World Wide Web advertising actually began just about the same time, early in 1994 (Briggs & Hollis, 1997). In the subsequent five years, advertising on the web has grown exponentially. Because appearance and disappearance of web advertising sites is common, and because ideas about what the Web will mean to advertising, both as a process and as an industry, come and go almost as quickly as the various sites themselves, Ad Age’s INTERACTIVE section provides a fascinating chronicle of the beginnings of Web advertising that is perhaps unlikely to be available anywhere else. For that reason, this chapter examines nearly five years of INTERACTIVE, discussing trends in the major issues that any new advertising medium must deal with: effectiveness with its audience, pricing, evaluating cost effectiveness, defining basic measurement units so a common language of web advertising can be developed, linkage with other media, either online or traditional, and so on. We also look at what this material means for academic and industrial researchers who must decide which aspects to invest in first, and what questions must be articulated.