This special's objective is to examine the question: do transgender athletes have a competitive advantage? Through interviews with transgender athletes and experts and personal storytelling, this special explores the myths and assumptions associated with competitive advantage and trans athletes.

Donald is shown in both animated and costumed form, interacting with emcee Dick Van Dyke and other cast members. The film not only shows Donald's life, but also depicts an extensive international tour that Donald went on in 1984 as well as showing various celebrities of the day wishing Donald happy birthday. The tour culminates in a parade in Donald's honor at Disneyland.

Matthew Cameron (Jay Richardson) is a lawyer undergoing a midlife crisis despite having a seemingly perfect life with his wife, advertising executive Jessica (Candy Clark), and his young son. When he champions a homeless shelter facing eviction, his problems only deepen. Matthew faces pressure from Jessica, whose agency is representing the corporate honcho pushing the eviction, and Matthew is forced to question his values and loyalties.

Pulitzer prize-winning reporter and author, Buzz Bissinger, experiences a sexual awakening while collaborating with Caitlyn Jenner on her tell-all memoir.