On July 8, 1989, a young music fan named Aadam Jacobs, with a compact Sony cassette recorder in his pocket, went to see an up-and-coming rock band from Washington for their debut show in Chicago.

Featuring works by Osamu Tezuka and Yoshitomo Nara, the auction will coincide with New York’s Asian Art Week later this month. The House of Pikachu: Art, Anime, and Pop Culture, presented by the Asia ...