History Film / Transamerica

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* 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]].

* ArmorPiercingQuestion: A little girl asks Bree out of the blue, "Are you a boy or a girl?"

* RecursiveCrossdressing: Bree is played by a cis woman playing trans woman.

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

Bree Osbourne 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; 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.

* 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.

* NiceHat: Calvin goes into the language of cowboy hat setting.

Bree Osbourne, formerly Stanley Osbourne, is a [[UsefulNotes/{{Transgender}} 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.

* 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.

Bree Osbourne, formerly Stanley Osbourne, is a [[{{Transgender}} 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.

* {{Transgender}}: Bree is a transgender woman.

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

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.

Although some consider it to be decent film in it's own right, many people in the transgender community 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. 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.

* InsaneTrollLogic: Toby's explanation of why TheLordOfTheRings is gay.

* 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.

* 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.]]

* RecursiveCrossdressing: Bree is played by a woman playing a man on his way to becoming a woman.

* {{Transgender}}

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".

* 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.

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.

* {{Transsexual}}

Bree Osbourne, formerly Stanley Osbourne, is a [[{{transsexual}} transwoman]] 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 transsexuals; so if you don't know much about transsexuals, 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".

* ActorAllusion: Bree is also one of Lynette's friends on Series/DesperateHousewives.

--> Bree's Mom: "He's still a boy!"

A 2005 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.

Although some consider it to be decent, many people in the transgender spectrum accuse the film of being stereotypical about it's portrayal of transsexuals; so if you don't know much about transsexuals, 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".

* {{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. By contrast we also see [[{{Fandisservice}} Bree's penis]].

* HeyItsThatGuy: You know the chief in ''DancesWithWolves''? He has a cameo. (He's also [[Series/TheRedGreenShow Edgar Montrose]].)
** Also, Bree's sister is Arlene from TrueBlood

* [[spoiler: ParentalIncest: 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.]]

* HeyItsThatGuy: You know the chief in ''DancesWithWolves''? He has a cameo. (He's also [[TheRedGreenShow Edgar Montrose]].)

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

* ActorAllusion: Bree is also one of Lynette's friends on DesperateHousewives.

Although some consider it to be decent, many people in the transgender spectrum accuse the film of being stereotypical about it's portrayal of transsexuals; so if you don't know much about transsexuals, 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 transgendered people usually get in the media, which is "none at all".