Pretty Fly for a White Guy



""Officer, you only pulled me over because I think I'm black.""

- Mad Magazine spoof of Eight Mile

Unless you are xenophobic or ethnocentric, you might find parts of other cultures to be interesting or cool. So you might have the urge to at least once in a while try to imitate part of that culture, like the dialect, slang, or accent. Now the problem is that you don't have a deep understanding of the culture's origins and meanings, so you should at least pay close attention to what you are about to imitate, preferably with some practice beforehand.

If you don't, you will look silly at the very least. Worse, in fiction, wars have started that way.

The most common form of this is likely just trying to imitate an accent. The most notorious form is middle class suburban white kids imitating the urban black culture. Note that it's the middle class culture, not the race, that determines whether someone's a poser. You can be Asian, Native American, Latino, or even African American, and still not be able to imitate the urban culture (and besides, the term "acting black" is chock full of Unfortunate Implications). The end result of this usually sounds Totally Radical to natives of said culture. These people are sometimes called "wiggers" combining the words "white" and a certain racial slur that white people generally avoid using. This version of the character, which was especially prevalent (and mocked) in The Nineties, is likely to become a Discredited Trope soon, as rap music, like rock 'n' roll decades before, has become mainstream enough so that white people who enjoy it aren't automatically labeled as posers. However, as long as there are subcultures associated with particular ethnic or socioeconomic groups, new versions of this trope will likely exist until the end of time.

One common variation is white people, usually Otaku, who are obsessed with Japanese culture. These people are often called "Wapanese" or, due to the efforts of 4Chan, "Weeaboos."

In more academic circles, this trope usually called cultural appropriation. This happens when a member of one culture takes on some of the trappings of another culture, such as clothing, music, and religious or political symbols. This is usually done for the sake of exoticism with a very superficial understanding of the environment in which the culture was born. While this is sometimes done to show tolerance and multiculturalism, it often results in the misunderstanding or misrepresentation of a culture.

This trope has some similarities to Blackface. The difference is that blackface is done to mock black people while this trope is done out of admiration or fetishization of black culture. However, if it's not done carefully, this trope can appear just as insulting as blackface. Also see Modern Minstrelsy.

See also White Gang-Bangers.

Anime & Manga

 * Bet you didn't see this coming did you? Actually, the "classic" depiction of Japanese Delinquents (face masks, triangle shades, pompadours, sarashi, etc...) in anime has decreased quite a bit in recent years, having been replaced by pierced youth in baggy "urban" wear (at mildest) to even full-blown wiggers (at worst).
 * Durarara!! had a bunch of them in episode 3.
 * Most infamously, the memetic "Hiroshi": "Yo, Yo, YO! HEY MAN!"
 * As Simon best put it, "Unfortunately there are guys like these in every country."
 * Agon of Eyeshield 21 dresses and behaves somewhat like a wangster, though he atleast has the sense not to talk like one. Still, even by Eyeshield standards, he looks rather silly with his long dreads, gold chain, and baggy pants.
 * Peepo Choo has Morimoto "Rockstar", an Ax Crazy yakuza boss who insists on dressing and acting like his own somewhat-distorted idea of an African-American hip-hop gangster.

Comedy

 * The Onion: Herbert Kornfeld, Accountz Reeceevin. Mourn ya till I join ya.

Commercials

 * In a series of commercials for T-Mobile, a gang of these represent their fictional competitor, Poser Mobile, in an obvious Take That against the hip-hop-themed ads for Sprint's Boost Mobile prepaid service.

Comic Books

 * In an issue of Gotham Central, Detectives Romy Chandler and Marcus Driver are chasing a couple of teenage white kids who speak and dress like hip-hoppers. When the kids get caught they profess their innocence and Romy points out that they assaulted an officer, which would mean time in juvie, where "you can see how much real brothers like rich white kids co-opting their culture, 'dog.'"
 * Pops up from time to time in the Swedish underground comic Rocky.
 * Phat from X-Statix is the scion of a rich family who poses as a hood rat as a ploy to get into what was at the time X-Force. It worked fantastically; evidently none of his teammates ever suspected he wasn't actually born and raised in an impoverished inner city home. Angry Black Man teammate the Spike has a problem with the Anarchist, an adopted black man raised by white parents, but not Phat.

Fan Fiction

 * From My Immortal, Snoop, AKA Snape, has a tendency to rap people when he gets mad. Also, Hargrid seems to be a fan of 50 Cent.

Film
"The Nostalgia Chick: This movie is whiter than Pride and Prejudice!"
 * Almost got a couple of kids beat up in Can't Hardly Wait, when they say to some of their black classmates, "What's up with my niggas!"
 * Not Another Teen Movie made fun of that, but with a white kid trying to be Chinese.
 * In a scene later on in the movie, he gets picked on by passing by white kids who think they're black.
 * Also calls a group of Asian students "chinks" and is promptly kicked in the face.
 * When actors play another culture, nationality or race that they don't understand. Even taking Unfortunate Implications out of this equation, they just look ridiculous. For example, the "How, White Man," portrayal of Native Americans in old movies, usually played by white people. Graham Greene tore that a new one in Maverick.
 * Trying to quell the controversy over Race Lifted characters in The Last Airbender, M. Night Shyamalan argued that the movie would be "culturally diverse," meaning the movie would star a bunch of white kids in Asian clothes.
 * In Ralph Macchio's (NOT Britney Spears') movie 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.
 * Collins in 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...
 * The 2007 Transformers brings us Jazz, an alien robot who deliberately takes on Jive Turkey mannerisms. He is voiced by Darius McCrary but that doesn't explain the gratuitous break dancing.
 * When Sam Witwicky is being questioned by the police, he sees one of the cop's guns, and that cop says, "You eyein' my piece, 50 cent?"
 * Sam even lampshades that line: "Are you on drugs?"
 * In the sequel, Revenge of the Fallen, the Twins are meant to be this according to Word of God. And since, functionally, they're callously imitating black culture as they see it on TV and such, this makes sense. However, as they were neither white nor black but bright orange and bright green, there was little physical anchor for the joke, meaning that most people who saw the movie thought they were meant to be caricatures of actual hood rats. (And quite a few people missed the mark entirely and thought they were supposed to be hillbillies.)
 * IDW comic's Drift is commonly interpreted as an Otaku by many fans, because that's the only way they can salvage a really horrible "character".
 * Parodied in Gran Torino, 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.
 * The Onion Movie has a young white man who goes around pretending he's black... who later gets arrested by two racist cops and jailed for crime he didn't commit based on the 'colour of his skin'.
 * 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).
 * An interesting variety of this is Willy from Stranger Than Paradise, a Hungarian immigrant to the United States who considers himself assimilated into American culture... which he apparently defines as acting like a 1950s beatnik.
 * Spike Lee's scathing 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 very eighties movie Teen Witch involved rapping by very white people.

"You see what's happening, don't you?! How we're being corrupted by their hipper-than-thou fashion and cool slang you can't help but use?!"
 * The movie 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.
 * Bery Gordy's The Last Dragon both plays this straight with a trio of Asian rapper wannabes and reversed with Bruce Leroy, who does the same with Chinese culture.
 * Undercover Brother.
 * White supremacist Mr. Feather constantly seems to have to battle to suppress an urge to be one of these. This causes him some stress.

"Mr. Morgan: I know how difficult it must be for you to overcome all those years of upper middle-class suburban oppression. Must be tough. But the next time you storm the PTA crusading for better... lunch meat, or whatever it is you white girls complain about, ask them WHY they can't buy a book written by a black man! White Rastas: That's right mon! Mr. Morgan: Don't even get me started on you two."
 * as well, as revealed at the end.
 * The pimp played by Gary Oldman in True Romance makes a great show of incorporating stereotypically black speech patterns, wearing dreadlocks, and watching Richard Pryor movies.
 * The entire movie Malibus Most Wanted
 * 10 Things I Hate About You - 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."


 * In Quigley Down Under, the Australian Marston is obsessed with The Wild West.
 * In Hidalgo, an Arabian sheik is fascinated by American culture and anything related to cowboys.
 * In Saving Private Ryan, 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.

Literature

 * The earlier Adrian Mole books contained the character of Adrian's classmate Danny: a white kid who had dreadlocks, wrote reggae music and spoke in a poor imitation of Jamaican patois.
 * He even referred to Adrian as a "honky". Adrian's response: "What a cheek, he's twice as white as I am!"
 * Thing is, he's Jamaican. He's just albino.
 * In Catch-22 they obviously hate Yossarian because he's Assyrian. Even if he's not. He isn't too serious about it, though.
 * A fantastic version appears in For The Emperor. Part of the population of Gravallax, due to being close to the Tau territories, absorbed their ideals and customs and looks up to them. Some go as far as to paint their skin blue. Justified:

Live-Action TV
" "How was the party?" " 'Twas a fine shindig indeed, arrrr!""
 * Jon Stewart mocks this in one of his more recent standup routines. He says that middle-class people (not just white people) shouldn't try to talk like inner-city gangsters, because they have no connection to that culture aside from what they see on TV. It would make as much sense for them to talk like a pirate (Talk Like a Pirate Day notwithstanding).

""Ah'm from Lincolnshire, wiv all da windmills and da potatoes and da shit...""
 * Yes, except that you never hear actual pirates complaining about Talk Like a Pirate Day.
 * Ali G from Da Ali G Show is a Jewish guy acting the part of a stereotypical white middle class wannabe who actually expects people to believe he's a black man from the ghetto. Ta-daa!
 * Ali G acts just like a sterotypical Indian /Pakistani teenager from the Staines/Slough (a couple a miles west of London) area where he is supposed to be from. Most British viewers, however, simply seem to view him as a stereotypical "chav".
 * This happens to Dr. Joel Fleischman in the Northern Exposure episode "The Mystery of the Old Curio Shop", when Fleischman tries to connect with the "Hebrew Heritage" of Cicely, Alaska. This is slightly subverted by the fact that Fleischman is himself Jewish, yet is still berated for trying to "act Jewish".
 * J.D.'s attempts in Scrubs at acting black usually fall disastrously short. Turk is generally more successful but is nonetheless called on this behavior when Dr Cox claims Turk isn't really black. Some of Dr. Cox's evidence is that Turk has a geeky white best friend, listens to Neil Diamond and acts like a black guy, which are traits only seen in white guys.
 * Jesse on Breaking Bad fits this trope perfectly.
 * Dog the Bounty Hunter when he tries to speak Pidgin.
 * This type is rather common among the miscreants seen on TruTV's Speeders or The Smoking Gun Presents.
 * Skins plays with this a little. Jal's two brothers have a white friend who fits this perfectly. Somewhat subverted, in that the brothers' own attempts at being "street" are shown to be just as ludicrous.
 * Parodied in Chappelle's Show, when a blind black Klan leader (long story short: he doesn't know he's black) encounters a group of (white) teenagers in a convertible listening to gangsta rap, assumes they're black, and yells racial abuse at them. Far from being offended, the teens are psyched that he thinks that they're street.
 * J-Roc from Trailer Park Boys does this and sometimes forgets he is white.
 * In The Thick of It, Oxbridge-educated posh boy Olly sometimes tries to put on a humourous Jafakean accent. The effect is ludicrous:

"Ray: Robert, we're Italian. The word "whack" means something else to us!"
 * One episode of Everybody Loves Raymond spoofed this trope. Ray's brother Robert, desperate to fit in with his African-American partner on the police force and her friends, spends most of the episode trying to act stereotypically "black." Raymond and the rest of the family are bewildered by this. At the end of the episode, Robbie's partner reveals to Ray that Robbie's new behavior is annoying and offending her friends, unsurprisingly. When Ray tells Robert about this, it results in the classic line:

"Jake: Yo, this sculpture's off the HOOK, yo!! Charlie: Jake, I'm not gonna say this again; you're a pasty white kid. Start acting like one!!"
 * Bozz Bishop from Nash Bridges.
 * Buckwild from Flavor of Love. Every single black person on the show calls her out on it. She has a hilarious Ooh, Me Accent's Slipping moment when she gets angry enough to forget her ghetto act.
 * Sebastian, alias C-Bass, from Halfway Home may be an actual black guy and he may be an actual convict. But he's from a very rich family and he went to prison for identity theft. His protests that living in a very big house can be inconvenient don't help the image he's attempting to cultivate.
 * Boardwalk Empire has the bootlegger Michael Kozik who changed his name to Mickey Doyle to better fit in with the Irish gangsters running Atlantic City. He is constantly mocked for it. However, he does not try to act particularly 'Irish' probably because the people he is trying to imitate are well integrated Irish-Americans who do not fit the stereotypes.
 * In Artie's case on Glee: White, nerdy, and wheel-chair bound, he frequently slips into stereotypically "black" slang (usually Rule of Funny), and it's fully expected that this trope is in full play.
 * In Two and A Half Men, Jake starts talking like this after watching MTV Cribs:

"T-Bag: "The boy sure seems confused about his pigmentation.""
 * David Apolskis on Prison Break. An inmate in the Fox River max-security prison which (like most real world prisons) is divided along racial lines, he quickly becomes rejected by both black inmates for trying to affiliate himself with them, and by white inmates for trying to affiliate himself with black inmates, earning him the nickname "Tweener" (In-Betweener). Lampshaded by T-Bag, the leader of a white racist gang:


 * Frog, a drug dealer from The Wire. So much that he is actually called out on this by Nick Sobotka.
 * Shmulie and David (both Orthodox Jews) in the Two Broke Girls episode "And the Kosher Cupcakes", when their mother's not around.
 * Mr. Drummond and Kimberly on Diff'rent Strokes occasionally.

Music
"Laugh along with the common people, Laugh along even though they're laughing at you, And the stupid things that you do, Because you think that poor is cool."
 * Named for the song "Pretty Fly for a White Guy" by The Offspring. It looks as though it's about race, but looking closer, it's clear the kid is just middle class, and has no idea of the actual hip-hop and ghetto culture. Thus he looks like an ass.
 * The Pulp song "Common People" is about the "slumming" phenomenon where upper class people try to live a working class lifestyle as a kind of "holiday", based on a real woman that Pulp singer Jarvis Cocker knew when he was studying at Central Saint Martins College of Art and Design. Some of the lyrics are particularly relevant:


 * The Sparks song Suburban Homeboy is all about this idea. "I'm a suburban homeboy, and I say Yo Dog to my pool cleaner guy..."
 * Like the Trope Namer, "Weird Al" Yankovic's "White and Nerdy" focuses on a white dork who wants to be gangsta.
 * Specifically, he wants to roll with the gangstas, but rather than imitating them, he spends most of the song describing just how nerdy he is.
 * Weird Al has actually covered the Trope Namer (as Pretty Fly For A Rabbi, which actually seems to invert the trope by being about an actual Jewish person who so excels at the stereotypes that he's well-liked for it).
 * Slightly more relevant is that Chamillionaire (to whom the parodied song "Ridin' Dirty " belongs) was pleasantly surprised by Yankovic's skill at rap.
 * For that matter, the sections of the British blues scene of The Sixties, at least for those less than authentic in their delivery or presentation. This, and the overexposure of blues and R&B influence then popular at the time, helped lead to the very British Progressive Rock scene. Ian Anderson felt he and his band were stealing a part of black culture and emotional experiences insincerely and not always convincingly, and that by strictly resigning himself to performing a "polite shade" of black American music he had little room for the full extent of music he wanted to make. He soon reinvented Jethro Tull as a very eclectic English/Scottish Progressive Rock band in The Seventies.
 * Tim "the Big Dawg" Westwood. Bizarrely, some people seem to think he actually pulls it off.
 * It helps that he's apparently a thoroughly pleasant bloke, isn't adverse to taking the piss out of his Big Dawg image, and actually knows a hell of a lot about the urban music scene (which he should, because it is his job). Watching him on the UK version of Pimp My Ride or hearing him guest on other shows talking about "watching Desperate Housewives with [his] lady" leads to a bit of Narm Charm rather than actually buying what he's selling.
 * Mr. B (the Gentleman Rhymer) mocks him splendidly here.
 * It could be argued that Mr. B's entire act is a deliberate defiance of this trope; proof that you don't need to act black to be a white rapper.
 * IT IS I, RAS TRENT! (There's even a part where he avoids trying to offend the actual Rastafari in the video.)
 * Fred Durst was considered this for a while, although he's gotten better.
 * Some music journalists use the semi-derogatory term "wigger slam" to refer to slam Death Metal bands, played by white guys who act and dress like black guys. See also the Deathcore page.
 * Tom Kaulitz, a German guitar player who has had his hair both in dreadlocks and cornrows and always sports clothes about 100 times too baggy for him. He even has his own shoe.
 * Eminem, though it's debatable. While he would be looked up to as an idol by pretty much everyone on this list and even wore an Africa pendant during high school, it should be noted that he came from an impoverished background and was engrossed in Detroit's hip-hop scene instead of simply imitating it. It helps that he stopped wearing baggy sweats and the like after he got sober.
 * Somewhat less debatable is Kid Rock, whose father was a used car salesman.
 * According to Cage, Rick Rubin attended one of Cage's early performances, dismissed Cage as "a wigga", and walked out.
 * Frank Zappa's song "You Are What You Is": The first verse is about this, while the second one is about the opposite situation.
 * American Black Metal bands are sometimes accused of this, based on the assumption that black metal is an essentially European artform.
 * A non-urban version is lampooned in Alan Jackson's 1994 hit song "Gone Country", although the song is often misinterpreted as being in favor of such a masquerade.
 * Canadian reggae artist Snow (born Darrin O'Brien) was often accused of this simply because, well, just look at his stage name. However, like Eminem, Snow came by it naturally, having grown up in the housing projects in Toronto that had a lot of Caribbean immigrants and thus was exposed to reggae and dancehall throughout his formative years. Having the best-charting and best selling reggae single in North American history helped too.
 * White rapper Kreayshawn, born Natassia Zolot, is receiving a lot of criticism for this. She is being accused of appropriating black culture. This criticism of her says that even the way she dresses is a Double Standard, since if a black female rapper were to do the same thing they'd be accused of being ghetto and uneducated.
 * Yelawolf is an aversion; like Eminem, he came from an impoverished background and happened upon hip-hop naturally by way of going to school in the Nashville projects and becoming acclimated with the music there. Furthermore, his topics seldom touch upon the inner city and focus more on the unpleasantries of Deep South life, which is what he was used to.

New Media

 * The source of the humor in this bash.org quote.
 * ...and this one on qdb.us as well.

Newspaper Comics
"Walt: "What? Don't people say Wazzup Dawg anymore?" Jeremy: "Dad, do us all a favor and talk like the middle aged white guy you are.""
 * Zits does this a number of times as well.

Professional Wrestling

 * WWE wrestler John Cena was Pretty Fly for a White Guy as a Heel. Then, he had a Heel Face Turn, and we were suddenly supposed to take his hip-hop posturing seriously. (It didn't help that he stopped actually rapping after his album was released and just made a lot of gay jokes in a "ghetto" accent.) Needless to say, the Narm thus created has led to massive amounts of X-Pac Heat whenever WWE hits any place that has an actual urban hip-hop culture. Thankfully, these days, he's toned down the hip-hop allusions in favor of becoming, essentially, an Ascended Fanboy, but the X-Pac Heat among Smart Marks may never completely subside.
 * Side note: Los Angeles has a very large "actual urban hip-hop culture," and Cena gets really loud cheers in L.A.
 * What Cena has been doing is fundamentally no different from what Elvis Presley did in The Fifties. He is a white, upper-middle-class American who, in his soul, does not feel like a white, upper-middle-class American, and acts accordingly. Far from mocking black culture, he is actually celebrating it, while putting a less menacing (white) face on it for his white fans. You may quibble about the Unfortunate Implications of all this, but it's really nothing new. (And interestingly, Cena's longtime nemesis John "Bradshaw" Layfield was essentially Cena in reverse: a boorish, trailer-park Texan who became obsessed with money and riches, and rebaptized himself as a Wall Street tycoon. This resulted in a bit of Hypocritical Humor when in 2006 JBL was doing a bit of color commentary on SmackDown! where he mocked Anna Nicole Smith; he is, in a way, basically her male equivalent.)
 * Too Cool. Brian Christopher and Scott Taylor as wannabe rappers dancing to hip hop beats and later adding former Wild Samoan Rikishi to their act ended being one of the more surprising hits of the Attitude era in the then-WWF. What made the gimmick work so well was the delightful randomness and heterogeneity of it: two skinny white men and a fat Japanese guy performing impromptu dance moves to a style of music that neither whites nor Japanese are ordinarily associated with.
 * Ray Gordy, currently known as Slam Master J is their 21st Century successor from the blonde cornrows down to the 50 Cent-like clothes, but so far, merely a jobber teamed with Jimmy Wang Yang, a subversion in that he's "pretty redneck for an Asian guy."
 * 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 in all three of the major promotions in the late 90s. This can also qualify as a Funny Aneurysm Moment as Dundee has shown himself to be an unapologetic racist in numerous shoot interviews since then.

Tabletop Games

 * In the latest editions of Shadowrun, of the flaws you can take, a few of them are Ork and Elf poser, which makes you the fantasy equivilent with obvious drawbacks.

Videogames

 * A variation: OG Loc from Grand Theft Auto San Andreas may be black himself, but it quickly becomes apparent that he's pretty bad at trying to be 'gangsta'. He does manage to make a music career out of it for a while, but that's only because he has CJ steal Madd Dogg's rhymebook.
 * Planescape: Torment has a variation: in the upper-middle-class-to-wealthy Clerk's Ward section of Sigil, you meet a group of "Clerk's Ward Thugs" who are poorly attempting to be "street", including hilarious misuse of the in-universe Future Slang common to the Hive (which, as the name implies, is a Wretched Hive). Annah, your party member who actually IS from the Hive, makes fun of them and threatens to fight them.

Webcomics
"EB: that's fine, you are entitled to your opinion, i am just saying that being a white guy who is a rapper with a ventriloquist doll is not cool by any stretch of the imagination or by any definition of word cool, ironic or otherwise. that's all i'm saying."
 * Dark Smoke Puncher from The Adventures of Dr. McNinja is an Irish-American ninja who effects stereotypical "Gangsta" mannerisms. Something of a subversion in that he only does this to prevent his parents from noticing just how incredibly nerdy he actually is.
 * Homestuck: Dave Strider and his Bro are, as described by Dave himself, "ironic rapping roof ninjas". Not much of Bro's work is seen (but plenty is seen of his love of puppeteering), but Dave was known to burst into improvised rap early on, he has a sizable array of sampling equipment and turntables, he sent Jade a collection of techno remix efforts of questionable quality, and in Sburb he even controls his time powers through augmented turntables. While Jade is impressed by it all, John and Rose don't really buy it all that much, and love to snark about or criticise it at many opportunities.


 * After having to clarify that the humans in Homestuck are aracial, Andrew changed 'white' in the above quote to 'Íæûë€Å', though it's since been changed back. He did this mainly to try and quell a Flame War on the forums.

Web Originals

 * In The Allen and Craig Show's two part Episode 8, Allen gets his very white, but maybe not so white, friend Lars, who he calls "the coolest guy I know" to keep Craig from becoming totally lame.
 * In Yu-Gi-Oh!: The Abridged Series, Jaden Yuki is portrayed as this, even rapping over the end credits.
 * The Nostalgia Chick will always complain when movies do this, but she's had a few cringe-worthy (if hilarious) moments herself when she's tried to act like a Sassy Black Woman.
 * This viral Facebook post.

Western Animation
"Carter: Okay, how do you spell "Kichwa?" Peter: Y'know what? Screw "Kichwa;" the name's Peter. P-E-T-E..."
 * In one episode of Family Guy, 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:

"Cartman: I was just down at the SPC, kickin' it with some G's on the West Si-eed..."
 * In a deleted scene for the episode "Stewie Kills Lois", Stewie sings a musical number threatening any "undesirable elements" in society in case of a rebellion against his world conquest. The very first one is "the white kid with the baggy clothes who's talking like he's black", which shows one of these dancing to hip hop in"gangsta" clothing, while a normally dressed white and black kid watch him in contempt.
 * In another episode, it is revealed that Lois has Jewish ancestry. Peter begins to fulfill the Jewish equivalent of this trope until a visit from the ghost of his hardcore Catholic father turns him into an anti-Semite.
 * Brian, due to his racist upbringing, barks angrily at a black man. Trying to smooth things over, Brian says how much he liked Benson.
 * Phineas of Phineas and Ferb tries to sound "street" in one episode by peppering his speech with the word dang. He comes off sounding more like a hillbilly than a gangsta. Ferb on the other hand raps pretty good considering the constraints of a Disney cartoon and the fact Ferb is usually The Silent Bob.
 * Of course, that's because they hired professional rappers to voice him.
 * The Boondocks presents Cindy McPherson. A blonde haired little white girl that runs her girl scout cookie fundraiser like a drug ring and will quote rap artists as inspiration for her behavior.
 * Ed Wuncler III and Gin Rummy from the same show. Both are white and come from affluent families (Ed in particular being the grandson of the wealthiest man in Woodcrest.) Both speak in copious amounts of jive, own lots of firearms that they are willing to whip out with the least excuse, rob convenience stores and banks despite having no pressing financial reason to do so, break into people's houses at night for burglary, and generally act in a over-the-top stereotypical "gangsta'" fashion. Ed and Gin even have African-American voice actors (Charlie Murphy and Samuel L. Jackson respectively) to complete the image.
 * Similarly, in The Haunted World of El Superbeasto, Velvet Von Black, who's lily-white and talks like a Jive Turkey, is voiced by Rosario Dawson.
 * At the beginning of The Fairly Odd Parents episode "Remy Rides Again", Chester tried to sound "slang", much to A.J.'s annoyance. It ended when A.J. electrocuted Chester.
 * Eric Cartman of South Park does this very briefly in "Cartman's Mom is a Dirty Slut", when he's trying to find his real father. When he's under the impression that it may be Chef, he dons the outfit in the page image and affects African-American vernacular (or at least, his understanding of it):

Real Life

 * US Presidential candidate Mitt Romney.
 * Also, Presidential candidate Hillary Clinton.
 * Presidential candidate Rick Perry, during controversy over a property of his named "Niggerhead", referred to African-American candidate Herman Cain as "brother" during a debate.
 * While reading a poem by a black poet, a black student was told by his white teacher to read it "blacker." The teacher then demonstrated what she meant. The results were not pretty.
 * There are some who believe Elvis Presley "stole" the music of African American artists. Rule of Cautious Editing Judgment applies here.