We'll start with "Romero". I think the first Romero ad ran in either Rock and Ice or Climbing, or both. I'll try to narrow the year down, but it was right around 1993 or so. The line was pulled from the Heminway novel, The Sun Also Rises. The ad was conceived and published by Chris Persinger, the in-house ad guy, seamstress, and bar tender at FISH Products at the time.
The banner ads below were all put up on RockClimbing.com when it first got going. The infancy of the web made stuff like this very affordable since nobody really even knew how many people were viewing pages or actually clicking on ads.