Transamerica (2005)

           In a remarkable performance that reminded me of Charlize Theron's transformation into Eileen Wuernos, Felicity Huffman plays a transsexual man named Bree who is a few days shy of having his male-to-female sexual reassignment surgery. When she discovers that she fathered a son long ago, her therapist will not sign off for the surgery until she confronts her past, so Bree travels to New York City and meets her son Toby. Toby is a street prostitute and drug abuser who aspires to make porn movies in Los Angeles. Bree poses as a missionary sort, and the two of them take a way-too-long and boring road trip from New York to California. This film did not work for me for many reasons. The relationship between Toby and Bree was not believable, nor was the film's ending. But Huffman's portrayal does an incredible job of capturing the pain, emotional isolation, and confusion of a person who lives in this nether world of unspoken taboos. She is intelligent, modest, deferential, homely, and has no interest in making any political statement. Why has this film been billed as a comedy? Anyone who has experienced these very real life issues would not find any of it laughable.