In 1999, the Magnetic Fields released 69 Love Songs, a three-CD collection of post-postmodern compositions that revealed writer Stephin Merritt as the most ambitious gay wit since Oscar Wilde. Queers have long excelled at irony; in 69 Love Songs, Merritt exploded the concept with his catalog of high-concept, lo-fi love songs about love songs about love songs that should’ve won him a Pulitzer. Instead, all he got was eternal glory and a hell of a lot to live up to.

David Schmader—former weed columnist and Stranger associate editor—is the author of the solo plays Straight and Letter to Axl, which he’s performed in Seattle and across the US. His latest...