->''"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'''

A 2005 comedy-drama film directed and written by Duncan Tucker, ''Transamerica'' starred Felicity Huffman just after her success on ''Series/DesperateHousewives''. Huffman received an Academy Award nomination for her role.

Bree Osbourne, formerly Stanley Osbourne, is a [[{{transsexual}} trans woman]] with a week before her big operation. 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, many people in the transgender spectrum accuse the film of being stereotypical about its portrayal of transgender people; so if you don't know much about trans people, you should be cautious about watching this. But it's not a ''negative'' portrayal and any portrayal ''at all'' is a big step up from the recognition transgender people usually get in the media, which is "none at all".

!!This film features examples of:

* 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 fucked up emotionally]] [[spoiler:[[RapeAsBackStory and sexually]]]] that he might not have a true orientation at all.
* ArmorPiercingQuestion: A little girl asks Bree out of the blue, "Are you a boy or a girl?"
* BadassNative: Toby thinks his dad is this, including a continuing belief that he's an Indian of some sort. Too bad for Toby, [[InformedJudaism he'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.
* [[CoolBigSis Cool Little Sis]]: Sydney.
* CrotchGrabSexCheck:
--> '''Bree's Mom:''' He's still a boy!
* DanBrowned: Everything to do with Bree's psychologist refusing to authorize her SRS: there's no way SRS could be scheduled before the psychologist approves it, and no competent doctor would refuse to authorize SRS for that reason. Since transition is such a complete mystery to the general public, most people wouldn't realize just how unrealistic the setup is.
* 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.
*** An example of RealityIsUnrealistic. Very few trans women ever have any kind of facial surgery - it's the magic of hormones.
* {{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 TheLordOfTheRings is gay.
* 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, Stanley 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.]]
* NiceHat: Calvin goes into the language of cowboy hat setting.
* 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]].
* RecursiveCrossdressing: Bree is played by a woman playing a man on his way to becoming a woman.
* 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.
* {{Transsexual}}
* 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."