October 12, 1998: "Offense Scores the Points, but will defense win tonight's game?" a.k.a. the most-generic NFL promo ever. (For the record, it was Dolphins at Jaguars.)
The AOL 4.0 promo in the top text spot is a repeat from Sunday; apparently we were on a push to promote AOL 4.0 downloads and didn't care much about the repetition. The headline, "You Can't Be First... but you can be next" is about as risqué as I got on the home page.
The internet these days seems to think that the quote is a Ric Flair thing, but I'm pretty sure it's much, much older. (I want to saw that it was popularized by a Mae West, bad girl-type, but I can't find a cite.)
[Series note: In the late 1990s, I programmed the content for the AOL.com home page, which relaunched with a new design on July 14, 1998.
I printed screencaps and saved them. 20 years later, I'm scanning them
in and posting them with a little commentary under the tag #20YearsAgoOnAOLcom.]