Gay America Pageants established its first male division in 1983 under Norma Kristie, Inc., led by Norman Jones and Carmel Santiago (Lady Baronessa, Miss Gay America 1974). Designed as a companion to the Miss Gay America pageant, this male contest provided a platform for gay men to showcase their intellect, community service, and talent. It quickly became a launching pad for many aspiring entertainers. As the first competition of its kind, its winner was regarded as a co-titleholder alongside the reigning Miss Gay America queen.

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In 1995, Jones sold the male contest to Gib Hauersperger, who had been serving as its director following the passing of Carmel Santiago. Hauersperger managed the pageant until his retirement in 1999, at which point Paul Lopez (the 2000 titleholder) took over. Lopez oversaw the contest until 2003, when Richard Greer (1999 titleholder) assumed the role of director. John Beebe (1996 titleholder) later succeeded Greer. In 2009, Beebe and Hauersperger announced that the male contest would cease operations indefinitely.

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In 2016, Michael Dutzer and Rob Mansman of Mad Angel Entertainment purchased the Gay America pageant. After successfully completing their first national competition, they decided to revive the male contest under the direction of Antwan Lee, also known as Asia O’Hara (Miss Gay America 2016), restoring its legacy and honoring past titleholders as part of the America family. The male division operated for three years before being sold following the COVID-19 pandemic in 2020 to Prideland Productions who operated it until 2024.  

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Now, Mad Angel Entertainment is reintroducing a male contest to complement the Miss Gay America and Miss Gay America Femme divisions, officially launching as Gay America Esquire in 2025.  The new division will be franchised and operated by KC Sunshine, the 2022 winner.