History Main / PrettyFlyForAWhiteGuy

* Music/MCHammer got this reaction with the 1994 album ''The Funky Headhunter''. He actually was a black man who, much like Jennifer Lopez above, grew up in the ghetto (Oakland, California in his case), and behind the scenes, he had connections to genuine criminals. However, he had built his career as a clean-cut, goofball pop-rapper, and so the attempt to shift to a DarkerAndEdgier style and sound in order to jump onto the GangstaRap bandwagon was seen by many as a pose carried out [[WereStillRelevantDammit just to stay relevant]]. His career [[CreatorKiller tanked]] as a result.

Another variation is white people, usually otaku, who are obsessed with Japanese culture. These people are often called "Wapanese" or, due to the efforts of Website/FourChan, "[[OccidentalOtaku weeaboos]]."[[note]]It is often said that you can still like the Japanese culture and not be a weeaboo, but if you reject your native culture in favor of a stereotyped and distorted image of Japanese culture formed from only consuming highly stylized media, that is being a weeaboo.[[/note]]

* ''Film/TenThingsIHateAboutYou'' - When Michael is showing Cameron around the school, one of the cliques he points out is the "White Rastas," who "think they're black" but "mostly smoke a lot of weed."

* Creator/SpikeLee's scathing film ''Film/{{Bamboozled}}'' has a spectrum of these characters, including a black TV executive acting painfully white, his white boss acting painfully ''black,'' a multiethnic gangsta rap band living up to all the wrong stereotypes (one of whom is white, yet protests that he's black while being busted by a cop who actually ''is'' black), and a TV show that's based around minstrel-show caricatures yet winds up being a hit with audiences of all ethnicities.
* The movie ''Film/{{Barbershop}}'' features a white guy who actually is from the streets and thus dresses, speaks and acts accordingly - who is offended when a nerdy middle-class black guy implies he's somehow pretending to be something he's not based solely on the color of his skin.
* ''Film/Bones2001:'' Downplayed with Tia, who comes from a predominantly white gated community. She doesn't use African-American slang, but does wear inner city-style sunglasses and head kerchiefs, while being fully on board with Patrick's plan to revitalize the African-American neighborhood he grew up in by opening a nightclub there. In her first scene, she's also wearing a tank top with pictures of a black celebrity on it.
* ''Film/{{Bulworth}}'' has ''Creator/WarrenBeatty'', of all people, becoming one of these as a result of a HollywoodMidLifeCrisis. He was a US Senator with falling popularity ratings until he snaps and randomly starts rapping at his campaign appearances (he even manages to seduce Creator/HalleBerry's character), and it culminates in a TV talk show appearance where he claims that the solution to racism is genetic mixing until "everyone's the same color." [[spoiler: Then he gets [[ShootTheShaggyDog mysteriously assassinated.]]]]
* Almost got a couple of kids beat up in ''Film/CantHardlyWait'', when they say to some of their black classmates, "[[NWordPrivileges What's up with my niggas!]]"
* In Ralph Macchio's ('''NOT''' Music/BritneySpears') movie ''Film/{{Crossroads}}'', the lead character idolizes blues music, but he looks at it as purely an art form. It only penetrates that the blues is a state of mind and heart when the love interest abandons him without even saying goodbye.
* Hoopz from the ''Film/WrongTurn''-esque ''Film/{{Detour}}''. Surprisingly, he survives the entire film.
%% * In ''Film/DirtyLove'', Music/CarmenElectra plays the protagonist's TokenBlackFriend. Yeah.
* In ''Film/DownToEarth2001'', Creator/ChrisRock plays a stand-up comedian who dies and whose soul is put into the body of a wealthy middle-aged white guy. So, now you got a typical white board member acting and talking like, well, Chris Rock. To everyone but him, he looks like a typical example of this trope. He even gets punched out once by a pair of black guys for singing along to "[[Music/{{DMX}} Ruff Ryders' Anthem]]" in a public place, and the audience's reaction when he goes to a comedy club at a black neighborhood and starts to deliver his usual routine is priceless. Then there is an attempt by the white guy's wife (played by Jennifer Coolidge) to act "street" to get his attention.
* A rather interesting one from 1935 in the film ''Film/TheGhostGoesWest'': Mr. Martin, a Capitalist American, wears a kilt even though he doesn't have one ounce of Scottish blood. Then, when Donald Glourie, an actual Scotsman, shows the tradition of having bagpipers play before dinner, Martin does the same thing when he introduces his new castle in Florida except with jazz musicians. Which comes off as Americanized cultural appropriation of In-universe Scottish traditions.
* In ''Film/GirlsTrip'' Ryan's assistant/agent is played by Creator/KateWalsh and tries to be "down" with her boss. Emphasis on "tries." It's more "trying to relate" than full-on "cultural appropriate."
* Parodied in ''Film/GranTorino'', where a young white man's pretending to be black first just pisses off three actual black youths, and then earns him a scathing assessment from Walt (Clint Eastwood). Especially funny in that the white youth in question is played by Eastwood's son.
* In ''Film/{{Hidalgo}}'', an Arabian sheik is fascinated by American culture and anything related to cowboys.
* Collins in ''Film/{{Idiocracy}}''. Interestingly, he seems to hit it off pretty well with Upgrayedd ("With two D's for a 'double dose' of his pimping"), if his slide show is anything to go by. Part of the reason that the plot happens, furthermore, is that Collins ends up getting arrested by military police. It's implied that he took to the pimping lifestyle a little too closely...
* ''Film/TheLastDragon'' both plays this straight with a trio of Asian rapper wannabes and reversed with Bruce Leroy, who does the same with Chinese culture.
* The entire movie ''Film/MalibusMostWanted''. This also applies to one of the black actors hired to portray thugs from the hood. Being a trained actor, he doesn't know much about life in the hood. He is even shown reading an urban dictionary at one point, trying to learn words like "wack" and "dis".
* ''Film/MarciX'' has to show, on stage at a rap concert, that she is real. She succeeds.
* Lincoln from ''Film/MotorHomeMassacre''. Unlike the above, this slasher does not make the mistake of letting this obnoxious character live.
* ''Film/NotAnotherTeenMovie'' made fun of that, but with a white kid trying to be Chinese as an inversion of Long Duk Dong from ''Film/SixteenCandles''. He calls a group of Asian students [[NWordPrivileges "chinks"]] and is promptly kicked in the face. In the opening scenes, he gets picked on by some white kids who think they're black.

* ''Film/TheOnionMovie'' has a young white man who goes around pretending he's black... who later gets arrested by two racist cops and jailed for a crime he didn't commit based on the 'colour of his skin'.
* Both played straight and averted in ''Film/QueensLogic''. Eliot (John Malkovich) describes his friend Denny (Creator/KevinBacon) as having "problems"; "He's a white man who thinks he's Music/JamesBrown."

* In ''Film/QuigleyDownUnder'', the Australian Marston is obsessed with TheWildWest.
* In ''Film/SavingPrivateRyan'', a German soldier is captured by Americans. Fearing execution, he starts sucking up to them by talking about American pop culture and butchering the Star-Spangled Banner.
* ''Film/ScaryMovie3'' has a subplot spoofing ''8 Mile''. George Bitner is a whitebread farm boy who has two black best friends and participates in rap battles. When his older brother denounces his interests, George declares "You just hate me cuz I'm black."
* In ''Film/ScoobyDoo'', the teens leaving the mysterious island all appear to fit this trope, despite being predominantly white. [[spoiler:They're actually demons disguised as "typical American teenagers", studying "proper slang" to fit in]].
* In ''Film/{{Stiletto}}'', the gangster known as [[OnlyKnownBytheirNickname Large Bills]] used to be associated with a Neo-Nazi biker gang until he he abandoned them to ally with a black gang because it was more profitable. He has assimilated well, and become a big fan of black culture (with one character even stating Large bills wishes he could actually be black. He seems to have been accepted by his new allies who even afford him NWordPrivileges.
* An interesting variety of this is Willy from ''Film/StrangerThanParadise'', a Hungarian immigrant to the United States who considers himself assimilated into American culture... [[DiscoDan which he apparently defines as acting like a 1950s beatnik]].
* The French film ''Il était une fois dans l'oued'' is about a Frenchman who adopts an Arab lifestyle and moves to Algeria. He tries to convince everyone he's the real thing even though he doesn't look Arab at all. (For the sake of accuracy, it is worth noting that there ''are'' some people in Algeria whose features are European and who may even have blond hair, but the film doesn't dwell on this).
* The ''very'' [[TheEighties eighties]] movie ''Film/TeenWitch'' involved rapping by ''very'' white people. However, hip hop was still a very young genre at the time of filming, with many of its conventions still unformed, so it's more a case of TotallyRadical.
* In ''Film/TourDePharmacy'', this is an ExaggeratedTrope with Marty, who is a white person of American descent born and raised in Nigeria and touts being the first Nigerian in the Tour de France [[spoiler: (and when Slim Robinson, an African-American wins, he bemoans the fact that an African such as himself didn't win)]]. In reality, he attended American schools and didn't interact with any actual black Nigerians.

* The pimp played by Gary Oldman in ''Film/TrueRomance'' believes that he's black, but he's actually a mix of several races. He makes a great show of incorporating stereotypically black speech mannerisms, wears dreadlocks, and makes racist comments against white people he meets.

* Winston in ''Film/{{Us}}'' may be a black man, but he's a decidedly upper-middle-class black man who drives a luxury SUV and owns a lake house and a boat. We see him early on playing the classic '90s rap song "I Got 5 on It" on the car's stereo and singing along, to which his kids respond with [[AmazinglyEmbarrassingParents embarrassment]]. He makes for a sharp contrast with his [[EvilDoppelganger "tethered" double]] Abraham, who exhibits all the characteristics of a ScaryBlackMan.

* Zack from ''Film/{{Zebrahead}}'' is a white Jewish boy who talks like a black guy, listens to black musicians, and records rap music. Those traits combines with his friendship with Dee and romance with Nikki, who are both black, lead some of his classmates to accuse him of wanting to be black, although he says he's just being himself.

* The former game-centric retail chain, Game Crazy's, [[https://www.youtube.com/watch?v=441yNVdmVU4 training video]] is loaded with out-of-date attempts to appeal to "gamer culture." Especially Zelda, who speaks almost entirely in 90s ghetto slang despite being white as porcelain.

* ''WesternAnimation/TheNightmareBeforeChristmas'': Jack Skellington's attempts to imitate Christmas celebrations are presented as a case of this, as he has absolutely no idea what those celebrations are actually about and filters those celebrations are actually about and [[TwistedChristmas filters them through the dark, creepy sensibilities of Halloween]] that he's familiar with. The result: [[CrappyHolidays he ruins Christmas]].

%% * In ''Film/{{Dirty Love}}'', Music/CarmenElectra plays the protagonist's TokenBlackFriend. Yeah.
* In ''Film/DownToEarth'', Creator/ChrisRock plays a stand-up comedian who dies and whose soul is put into the body of a wealthy middle-aged white guy. So, now you got a typical white board member acting and talking like, well, Chris Rock. To everyone but him, he looks like a typical example of this trope. He even gets punched out once by a pair of black guys for singing along to "[[Music/{{DMX}} Ruff Ryders' Anthem]]" in a public place, and the audience's reaction when he goes to a comedy club at a black neighborhood and starts to deliver his usual routine is priceless. Then there is an attempt by the white guy's wife (played by Jennifer Coolidge) to act "street" to get his attention.

* Non-white example: An common point of criticism against [[KoreanPopMusic Kpop]] is its fetishism of black culture. As a result of both the sudden rush of Western music into Korean radio in the Eighties[=/=]Nineties and Seo Taiji' & Boys' success after combining [[GenreBusting various Western sounds]], Kpop is similarly influenced by many Western genres, ''especially'' 90s HipHop and RAndB. However, this meant that these genres were simply adopted by the idol industry as a means to get higher sales without much of a look into racial/cultural context: Hip-Hop tends to be treated more as an image thing, with many idols dressing or acting "black" for a concept; the obligatory rappers in idol groups are more often than not "trained" to rap and don't necessarily even write their own lyrics. The fact that Korean media in general also has had many incidents related to anti-black racism (some even involving idols doing {{Blackface}}) doesn't help matters.

** Ork posers, meanwhile, universally cleave closer to this trope and consist of elves and humans who think ork culture in the sixth world is cool. They tend to dress up as orks, hang around orkish circles in attempt to fit in, run with orks and [[NWordPrivileges try to work anti-ork slurs like "tusker" into their vocabulary]]. Surgery to look orkish is very rare. Orks tend to react badly to ork posers, though the occasional poser can earn a seat at the table through luck, dedication and respect. They're usually seen in the same light as white GangstaRap fans were during the early nineties by humans.

* Music/MeghanTrainor, who hails from a White Anglo-Saxon Protestant family, was already musically influenced by Motown and R&B on her early albums but began appropriating black urban culture in earnest starting with [[BreakthroughHit "All About That Bass"]].

* Music/DavidBowie's short film ''Jazzin' for Blue Jean'' (an extended music video for the single [[Music/{{Tonight}} "Blue Jean") has his StrawLoser protagonist Vic trying to ingratiate himself with a black bouncer at a club he's trying to get into, with results that smack of this trope. He thinks Malcolm X is a band and claims he caught their tour and seems to be confusing Jesse Jackson with ''Michael'' Jackson! Bowie himself had a huge amount of appreciation for Black culture, and Vic's cluelessness about that very topic ties in with his characterization as a direct antithesis of his actor.

* Music/JustinBieber could be described as this when you take into account his clothing and manner of speech - in particular, his overuse of the word "shawty".
* Music/DavidBowie's short film ''Jazzin' for Blue Jean'' has his StrawLoser protagonist Vic trying to ingratiate himself with a black bouncer at a club he's trying to get into, with results that smack of this trope. He thinks Malcolm X is a band and claims he caught their tour and seems to be confusing Jesse Jackson with ''Michael'' Jackson!

* Roundly mocked in the music video for {{Music/NWA}} protege The D.O.C.'s video for The Formula, with Music/DrDre and Music/EazyE holding audition for a new act. One of the groups that comes to the studio calls themselves [[Music/NewKidsontheBlock New Kids In the Hood]]. They're exactly what you expect.

* Pat Monahan of Music/{{Train}} tries to do this in "Hey Soul Sister" - it is IMPOSSIBLE to take him seriously when saying "I'm so gangsta, I'm so thug".

** Weird Al has actually covered the Trope Namer as ''Pretty Fly for a Rabbi'', which [[InvertedTrope inverts things]]: the Rabbi in the song is popular and cool because of how good he is at being Jewish.

* In ''WebVideo/EpicRapBattlesOfHistory'', Creator/ElvisPresley uses this to diss Creator/MichaelJackson:

* The Memphis-based {{tag team}} PG-13 (Wolfie D and Jaime "JC Ice" Dundee) were likely the first wrestlers to use this as a gimmick. They would go on to have stints [[Wrestling/{{WWE}} in]] [[Wrestling/{{ECW}} all]] [[Wrestling/{{WCW}} three]] of the major promotions in the late 90s. This can also qualify as a FunnyAneurysmMoment as Dundee has shown himself to be an unapologetic racist in numerous shoot interviews since then.

* Like the Trope Namer, Music/WeirdAlYankovic's "White and Nerdy" focuses on a white dork who wants to roll with the gangstas, but rather than imitating them, he spends most of the song describing just how nerdy he is.

* Jews for Jesus is an organization of Jews who converted to Christianity. They often stress the commonalities between the Jewish and Christian religions or re-interpret Jewish texts and rituals to make them more Christian. To many Jews, they end up as this trope or worse, especially since they're most heavily associated with highly anti-Semmetic Christian sects.

* Creator/{{RuPaul}}'s FagHag Michelle Visage first became known in the LGBTQ+ community (and eventually became friends with Ru[==Paul) when she became the first white girl to compete in New York City's vogue ballroom scene, which is normally the domain of queer people of color.

* Creator/RuPaul's FagHag Michelle Visage first became known in the LGBTQ+ community (and eventually became friends with Ru[==Paul) when she became the first white girl to compete in New York City's vogue ballroom scene, which is normally the domain of queer Blacks and Latinos.

* A good half of Creator/ChanningTatum's roles. The other half is "Southern guy who beats up people".

* Jews for Jesus is an organization of Jews who converted to Christianity. They often stress the commonalities between the Jewish and Christian religions or re-interpret Jewish texts and rituals to make them more Christian. To many Jews, they end up as this trope or worse.

** Weird Al has actually covered the Trope Namer as ''Pretty Fly for a Rabbi'', which [[InvertedTrope inverts things]]: the Rabbi in the song is popular and cool [[YouHaveToHaveJews because of how good he is at being Jewish]].

* Music/JustinTimberlake, despite being raised in suburban Memphis, wore [[https://twitter.com/maddie_murr_/status/318929517584478209?s=21 corn rows]] and [[https://twitter.com/newbodymusic/status/1034908815651557376?s=21 durags]] during his Music/{{NSYNC}} days and uses [[https://twitter.com/net_twink/status/1238035535618134019?s=21 Black slang]] as well. His proximity to Black culture has been questioned in light of the unequal treatment he and Music/JanetJackson received in response to the 2004 Super Bowl mishap; while Justin apologized (after first bragging about it being planned), his career soared, while Janet was blacklisted by radio and Les Moonves. Justin has [[https://theoutline.com/post/2839/justin-timberlake-man-of-the-woods-pivot joked]] about the trope in 2011. But it didn’t help that his 2018 album ''Man of the Woods'' was marketed with [[https://twitter.com/intergalacticq/status/1154162651238404097?s=21 country aesthetics]], leading much of the press to mock him for [[https://wifflegif.com/gifs/373711-jusitn-timberlake-kevin-hart-gif “rebranding as a white man”]] after years of making R&B and hip hop-friendly music.

* In the early days of his career, Music/JustinTimberlake was considered by many to be this trope, especially since he came from suburban Memphis but grew up in suburban Orlando and even joked about it himself. Music/{{NSYNC}} even mocked it in "U Drive Me Crazy" where they disguised themselves as a rap group to get the attention of a music executive, who saw right through them.
-->'''Justin''': I'm pretty sure I thought I was black then anyway.

** In one episode, Chris becomes the towel boy for the high school basketball team and picks up some slang and mannerisms from the black players. His father Peter investigates their heritage, with the intention of familiarizing Chris with their Irish roots, and discovers a black slave among his ancestors. Then Peter starts trying to act like a black man and goes entirely too far; wearing a dashiki, insisting that he be called Kichwa Tembo, and demanding reparations from his father-in-law. Hilariously, he discards his new identity the moment Carter whips out his checkbook:

* Stan Smith of ''WesternAnimation/AmericanDad'' is known to do this fairly regularly, which stands in contrast to his otherwise very conservative mannerisms.