37. Transamerica (2005): This award-winning film, starring Felicity Huffman in an Oscar-nominated performance as transgender woman Bree, admittedly doesn’t get everything right when it comes to portraying a fully developed trans character on the big screen. For starters, Huffman is a cisgender (nontrans) woman, whose character discovers that she fathered a son who is now a teenage runaway living in New York. Cue the trans-as-surprise-twist critique. But the film, which had trans woman and vocal coach Andrea James as a consulting producer, was a substantial step forward in mainstream visibility for transgender characters, and remains an accessible way to introduce folks wholly unfamiliar with the concept of gender identity to a sympathetic depiction of some of the struggles that come from seeking an authentic life. —S.B.
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