The Adventures of Sebastian Cole (1999)

Growing up in upstate New York, seventeen-year-old Sebastian Cole wants something else. He wants to get out and find adventure, new experiences. Little does he know life has plenty in store for him... Sebastian's family is suddenly thrown into a fantastic tailspin when his stepfather Hank announces that he is going to become a woman. In response, Sebastian's sister runs off to California with her boyfriend, and his hysterical mother Joan whisks him back with her to her native England. Unhappy with his new surroundings and his mother's coping through inebriation, Sebastian returns to New York. Instead of living with his phenomenally egocentric biological father Hartley, and his new trophy wife, Sebastian moves back in with Hank, now a macho pre-op named Henrietta. The two form an unlikely family.