My wife (b. 1978) and I (b. 1977) have a running discussion of 1 hit wonders and what a show like this would be like. We decided that these bands/artists would only be songs from 1980-1999 and would fall within the confines of a "One Hit Wonder" as defined by Wikipedia (https://en.wikipedia.org/wiki/One-hit_wonder)

We also decided there would be 2 sets - 1 for rock and 1 for R&B/hiphop.

Lets create a lineup. I have "Closing Time" by Semisonic as the final song of the encore.