HIGH AS THE SKY takes place on the South Side of Chicago, where Ken Ryan and his husband Mark have just returned home for Christmas. But this is no ordinary holiday – Ken and his siblings have planned a surprise for their mother Nancy, a first class trip to Hawaii. What would have been a magical vacation turns into tragedy when Nancy dies of an unexpected heart attack just before leaving. As Ken, his brothers Tom and Jim, and their sister Holly are faced with immense grief, they must also decide how to care for their elderly grandmother, who had been living with Nancy. Once a larger-than-life presence within the family, Gram’s mental faculties are not what they used to be.
In order to keep a promise to Nancy that Gram never be sent to a nursing home, Ken temporarily moves back to Chicago with Mark. As they struggle with her care and the family tensions that arise from it, they must deal with the discrimination of a major newspaper, the Chicago Tribune, which had refused to print Nancy’s death notice because the family listed Mark as Ken’s spouse.
When Ken realizes that a number of people didn’t attend Nancy’s funeral, he is devastated by the impact of the Tribune’s actions and refuses to accept this blatant homophobia. Vowing not to be treated like a second-class citizen, he sues the Tribune, sparking a legal conflict that examines one of the most controversial issues of our time – gay civil rights.