History Main / PrettyFlyForAWhiteGuy

* Music/VanillaIce, although he did come from a lower-class background and got his nickname by way of being the [[TokenMinority only white kid]] in his circle of friends. Most of the actual examples of this trope with him either came later or weren't even of his doing.

* ''Film/{{Transformers}}'':

* ''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 [[TwistedChristmas filters them through the dark, creepy sensibilities of Halloween]] that he's familiar with. The result: [[CrappyHolidays he ruins Christmas]].

* Music/{{Pink}} heavily invoked this [[EarlyInstallmentWeirdness on her first album]], riding the '90s Contemporary R&B bandwagon, but dropped the act afterwards.

* Many NuMetal bands got accused of this because of their hip-hop influences, use of turntablists, and ''especially'' because of how some of the them dressed. With Music/{{Korn}} and Music/LimpBizkit being the two biggest offenders.

** Downplayed with "White Mike" [=McArdle=], a white drug crew boss who works alongside Proposition Joe's organization. His street mannerisms being more downplayed and subtle.

%%* Music/MileyCyrus' "We Can't Stop" and her twerk-heavy performance of it at the 2013 Video Music Awards was considered by many to fit this trope.

* In ''WebVideo/EpicRapBattlesOfHistory'', Music/ElvisPresley uses this to diss Music/MichaelJackson:
--> '''Elvis:''' "I stole from ''black'' culture, why are ''you'' offended?"

** In Music/BritneySpears' memoir ''The Woman In Me'', at one point she talks about how she felt *NSYNC was trying ''way'' too hard to fit in with black musicians during their heyday when she and Timberlake were a couple. She describes an instance where he once put on an extremely forced blaccent when he and Spears came across R&B singer Music/{{Ginuwine}}: "Oh yeah! Fo' shiz! Fo shiz! Ginuwine!" Better yet, the audiobook is narrated by Creator/MichelleWilliams, meaning ''she'' of all people had to act this out. Clips of this passage have since gone viral due to the absurdity of it all.

* Similar to the Madonna example, OneHitWonder Bobby Caldwell faced this with his 1978 R&B hit, "What You Won't Do for Love". Record labels wanted to avoid this trope, so they didn't put his face on the album cover because they feared it would scare off black audiences. When he toured with Natalie Cole, audiences were shocked that he was actually a white man.

** In Music/BritneySpears' memoir ''The Woman In Me'', at one point she talks about how she thought *NSYNC tried ''way'' too hard to fit in with black musicians during their heyday when she and Timberlake were a couple. She describes an instance where he once put on an extremely forced blaccent when he and Spears came across R&B singer Music/{{Ginuwine}}: "Oh yeah! Fo' shiz! Fo shiz! Ginuwine!" Better yet, the audiobook is narrated by Creator/MichelleWilliams, meaning ''she'' of all people had to act this out. Clips of this passage have since gone viral due to the absurdity of it all.

** In Music/BritneySpears' memoir ''The Woman In Me'', at one point she talks about how she thought *NSYNC tried ''way'' too hard to fit in with black musicians during their heyday when she and Timberlake were a couple. She describes an instance where he once put on an extremely forced blaccent when he and Spears came across R&B singer Music/{{Ginuwine}}: "Oh yeah! Fo' shiz! Fo shiz! Ginuwine!" Better yet, the audiobook is narrated by Creator/MichelleWilliams, meaning ''she'' of all people had to imitate Timberlake trying to sound ghetto. Clips of this passage have since gone viral due to the absurdity of it all.

** In Music/BritneySpears' memoir ''The Woman In Me'', at one point she talks about how she thought *NSYNC tried way too hard to fit in with black musicians, and in a particularly memorable moment, she describes how Timberlake once put on an extremely forced blaccent when he and Spears came across R&B singer Music/{{Ginuwine}}: "Oh yeah! Fo' shiz! Fo shiz! Ginuwine!" Better yet, the audiobook is narrated by Creator/MichelleWilliams, meaning ''she'' of all people had to imitate Timberlake trying to sound Black. Clips of this passage have since gone viral due to the absurdity of it all.

** In Music/BritneySpears' memoir ''The Woman In Me'', she talks about how she thought N*SYNC tried way too hard to fit in with black musicians. In one of the book's most unintentionally hilarious moments, she talks about how Timberlake would put on an ''extremely'' forced blaccent when coming across Music/{{Genuwine}}: "Oh yeah! Fo' shiz! Fo shiz! Genuwine!" Better yet, the audiobook is narrated by Creator/MichelleWilliams, meaning ''she'' of all people had to imitate Timberlake trying to sound Black. Clips of this passage have since gone viral due to the absurdity of it all.

* 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 sometimes 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 stations and Creator/{{CBS}} executive Les Moonves. Justin has [[https://wifflegif.com/gifs/373711-jusitn-timberlake-kevin-hart-gif 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://theoutline.com/post/2839/justin-timberlake-man-of-the-woods-pivot “rebranding as a white man”]] after years of making R&B and hip hop-friendly music.

* ''Anime/{{Pokemon}} XY'', of all things, features a pair of kids with backwards hats constantly spouting "YO YO YO!" while striking goofy poses and pointing, at least in the Japanese version.

* J.D.'s attempts in ''Series/{{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 [[JiveTurkey acts like a black guy]], all of which are traits seen in white guys. Dr. Cox also mentions that Turk is merely the tenth best basketball player out of the mostly white hospital staff. This is partly a result of the show's shifting characterization and {{Flanderization}}: early seasons played off the SaltAndPepper pairing of JD and Turk much more, with Turk having a much more authentically "urban" persona with a [[BlackAndNerdy geeky, nerdy streak]]. Then there was that time Turk got schooled on black culture by the two whitest chicks in the hospital.