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->''"After my operation, not even a gynecologist could tell there's anything out of the ordinary with my body. I will be a woman."''
-->-- '''Bree Osbourne'''

''Transamerica'' is a 2005 comedy-drama film directed and written by Duncan Tucker, starring Creator/FelicityHuffman just after her success on ''Series/DesperateHousewives''. Huffman received an Academy Award nomination for her role.

Bree Osbourne (Huffman) is a [[UsefulNotes/{{Transgender}} trans woman]] who will soon receive gender affirming surgery. However, she soon discovers that she has a son named Toby. Her psychiatrist, upon hearing of this, refuses to grant her consent for the surgery and forces her to connect to Toby. Thus begins a rather interesting road trip from Los Angeles to New York and back again.

Although some consider it to be decent film in its own right, many people in the transgender community accuse the film of being stereotypical about its portrayal of transgender people (starting with having a cisgender actor portray a trans person); so if you don't know much about trans people, you should be cautious about watching this. Like with many things in Hollywood, any portrayal '''''at all''''' of social, ethnic and gender minorities is a '''big''' step up from the recognition transgender people usually get in the media, which is to say, "none at all". Especially true for this film as it came out in ''2005'', where discussions about gender expression in media such as films wasn't exactly mainstream.

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!!This film features examples of:

* ActorAllusion: Bree is also one of Lynette's friends on ''Series/DesperateHousewives''.
* AmbiguouslyGay: Toby. While he spends most of the film talking about (and having) sex with men, it's pretty clear his sexuality is largely targeted at whomever will give him the most attention and/or money, and there certainly aren't a lot of women soliciting teen boy hustlers. Of course the point might all be moot, since Toby's [[TroubledButCute so screwed up emotionally]] [[spoiler:[[RapeAsBackStory and sexually]]]] that he might not have a true orientation at all.
* BadassNative: Toby thinks his dad is this, including a continuing belief that he's an Indian of some sort. Too bad for Toby, [[InformedJudaism she's not]].
* {{Bowdlerized}}: Lifetime replaced "dick" with "thing" repeatedly. Because that's the only thing that {{Moral Guardian}}s hate about this movie.
* BraidsBeadsAndBuckskins: Subverted. Toby is surprised that Calvin, a Native American man who falls in love with Bree, would wear a cowboy hat. Calvin responds that it keeps the sun out of his eyes better than a feathered headband.
* BuffySpeak: "I can still see the Stanley in you. But it's like you put yourself through a strainer and got rid of all the boy pulp!"
* TheComicallySerious: Bree is hysterically prissy and uptight, which is perfect for a road trip movie across the Great Plains.
* TheCameo: Trans activist Calpernia Addams, one of the consultants on the movie, has a cameo, playing fiddle and singing.
* [[CoolBigSis Cool Little Sis]]: Sydney.
* CrotchGrabSexCheck:
--> '''Bree's Mom:''' He's still a boy!
* DeadpanSnarker: Bree.
--> "Eat your vegetables. You might wanna use a fork. Just an idea."
* DepravedBisexual: Toby is a prostitute who snorts any substance he can find and whose dream it is to make it into porn. He really doesn't care what sex he sleeps with, so long as they can be with him for that moment.
* DifferentForGirls: Avoided; Bree is well-adjusted psychologically as a woman.
* EasySexChange: Averted; the movie starts when Bree's psychiatrist refuses to authorize her sex change unless she reconciles with Toby. And in the opening voiceover of the film, we hear Bree discussing the sheer number of things she's had to go through to look even remotely feminine, including three separate face operations. Then she has to get electrolysis to remove those last few pesky nose hairs.
* {{Fanservice}}: Kevin Zegers (Toby) gets naked several times, to the point that his body could be considered the third main character. The Peyote Shaman offers some great views too, including a full fontral. We also see Bree's penis.
* FreudianExcuse: [[spoiler: Toby turned to drugs and prostitution because his step-father raped him repeatedly and his mother killed herself.]]
* GrammarNazi: Bree criticizes Toby for unnecessarily peppering his sentences with the word "like".
* HeteronormativeCrusader: Bree's mother hits just about every trope on the page.
* HookerWithAHeartOfGold: Toby.
* InsaneTrollLogic: Toby's explanation of why ''Film/TheLordOfTheRings'' is gay.
* {{Jerkass}}: The entire plot is kicked off by Bree's psychologist refusing to sign off on her surgery -- in spite of her desperate pleas that it takes place in a week and books a year in advance -- unless she reconciles with her son.
* LampshadedDoubleEntendre
-->"She's like a Jesus freak or something. She'll probably try to convert you."
-->"She can convert me anytime she likes."
* LampshadeHanging: People throughout the film mistake Bree for Toby's mother. And then there's the time Bree's sis [[spoiler:[[{{Foreshadowing}} thinks they're lovers]]]].
* LawOfInverseFertility: Bree is a complete virgin except for ''one'' time in college... If the math isn't adding up in your head, she supposedly spent ten years in college without ever getting a degree.
* LukeIAmYourFather: We know that Bree is Toby's father, but he doesn't.
* MissingMom: [[spoiler: Toby's mom killed herself when he was younger. This event was because she either found out about, or was the impetus of, Toby's step-father molesting him.]]
* ParentalIncest:
** [[spoiler: Sex is the only way Toby knows how to express affection, so when he begins feeling close to Bree, he offers to have sex with her. Bree's then forced to tell Toby the truth.]]
** [[spoiler: There's also the fact that Toby's step-dad molested him.]]
* ProgressivelyPrettier: Intentionally done with Bree. She starts out the film wearing ludicrous amounts of make-up to show that she's [[YouWereTryingTooHard trying too hard]] to look female. Later when the duo's [[spoiler: car gets stolen]], she has to stop wearing so much, and [[BeautifulAllAlong her natural femininity shines through]].
* SkewedPriorities: After Bree rescues Toby from a life of street prostitution and drug abuse, and after showing her his disgusting hole-in-the-wall of a room, Toby reveals his ambitions for a future in porn. When Bree looks (understandably) upset, Toby's greatest concern is that she not think he's a bottom.
* UnresolvedSexualTension: Bree and Calvin Manygoats are ''adorable'' together, and Calvin even gives her his number after she leaves. Now the question is just whether or not he could accept [[UnsettlingGenderReveal her past]].
* UnsettlingGenderReveal: Besides the obvious, Bree [[HypocriticalHumor disparages a lady in pink]] for never being able to pass as a woman. Her friend turns to Bree and says, "Check your T-dar, honey. She's a...genuine girl. That's the ''Mary Kay'' lady."
* ViewerGenderConfusion: InUniverse; a little girl asks Bree out of the blue, "Are you a boy or a girl?"
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