White People Who Tried Really, Really, Really Hard To Be Black, Ranked

Graham Denholm/Getty Images
Graham Denholm/Getty Images

From Rachel Dolezal to Colonel Sanders, American history is filled with examples of White Americans adopting and appropriating Black culture so aggressively that they started becoming kinda, sorta "Black" themselves. It's kinda like how my mom used to tell me that if I ate too many bite-sized Snickers, I would turn into a bite-size Snicker. Basically, they turned into bite-sized Black people.


But although many have done it, who did it the best? And by "best" I think I mean "worst." Let's see.

Late 90s to early 2000s Justin Timberlake

Although he seems to be back to regular Whiteness now, the JT from 15 years ago practically wrote the White boy guide for co-adopting Blackness by following the "Black R&B artist" script to a t.

To wit, he…

1. Went through an awkward cornrow phase

2. Helped Timbaland finance his multi-state Costco memberships

3. Won the support of Black women…and then threw a famous Black woman under the bus when shit hit the fan

Rachel Dolezal

The turducken of post-racial ridiculousness, perhaps the biggest takeaway from her saga is how it proves Black hair makes everyone — even aggressively plain White women — better looking.


Yay Black hair!

Gary Owen

Is it fair to put a White comedian on this list just because he's only funny to the Black people who like no other White comedians? And because he only appears in the Black movies Netflix recommends when you rent Soul Plane?


Yes. Yes, it is.

Randy "White Chocolate" Gill

Although he's somehow only the second most famous White basketball player nicknamed "White Chocolate," streetball veteran Randy Gill stands alone in his commitment to desperately attempting to be Black. Without giving you too much context about why he deserves placement on this list, just think of a grown-ass White man dressing, looking, and acting like a character Fredro Starr would have played in 1997.



When did we all collectively decide to forget that a White reggae rapper from Toronto had a number one song in 1993? 1995? 1997? 2002? Did it happen the same year we also decided to forget his name is an acronym for Superb Notorious Outrageous Whiteboy?


Iggy Azalea

There's nothing to say about the Australian Ali G that hasn't already been said. She's been humbled and humiliated enough, and I actually hope her and Nick Young have a beautiful wedding. At a remote, exotic locale. And have such a great time that they decide to stay there. Forever.


Elvis Presley

Rocked a gallon of pomade in his hair, was obsessed with footwear, and had loose hips. If this doesn't scream "White man wanting to be Black," I don't know what does. (And, if you include how Presley made millions doing and saying the exact same things Black artists had been doing for years for pennies and pre-owned Cadillacs, "Elvis Presley" = "Jon Stewart.")


John Howard Griffin and Ray Sprigle

Reading and researching about these two men who underwent skin transformations so they could write about being Black made me wonder why more White writers/bloggers/journalists don't attempt this today. Which then made me wonder if there actually are some doing it today, but they're so deep in disguise that they've fooled us all into thinking they're really Black. Which then made me look really, really, really hard at a picture of Toure.

Damon Young is the editor-in-chief of VSB, a contributing opinion writer for The New York Times, and the author of What Doesn't Kill You Makes You Blacker (Ecco/HarperCollins)



Urmmm no Riff Raff? Or is he too much of a parody to be considered as trying to be black?