The Otherwise Award, formerly James Tiptree Jr. Award, is an annual literary prize for works of science fiction or fantasy that expand or explore one's understanding of gender. It was founded in 1991 and is awarded every year at WisCon. 

The goal of this challenge is to read one winning or shortlisted work for every year. The prompts will only feature the winning title because I'm lazy. (Or smart? The 1995 shortlist featured 29 titles!) 
You can look up all the shortlists on the Wikipedia page "List of Otherwise Award Winners".

This challenge has no time limit. I will add future winners as bonus prompts after they're announced.