Dot-com commercials during Super Bowl XXXIV
Super Bowl XXXIV (played in January 2000) featured 14 advertisements from 14 different dot-com companies, each of which paid an average of $2.2 million per spot. In addition, five companies that were founded before the dot-com bubble also ran tech-related ads, and 2 before game ads, for a total of 21 different dot-com ads.
Source: Wikipedia — Dot-com commercials during Super Bowl XXXIV (CC BY-SA 4.0)