In case you were wondering, no, blackface is never okay. 
This recently past Halloween, and indeed in Halloweens of previous years, numerous individuals, famous or otherwise, have used the guise of the holiday as an excuse for all kinds of hate and discrimination — ranging from sexism to racism.
This Halloween has certainly been no less filled with controversial than others. The boundless source of knowledge and information, otherwise known as “the internet,” has been filled with scores of people donning all sorts of hateful and offensive costumes and disguises — all in the name of “having some fun for Halloween. “
Yes, it’s acceptable, and certainly encouraged to have fun in this rather festive season. But if the only way in which one can have fun is through the degradation of an entire race via the use of blackface, a tradition that is as rooted in the history of racism in America as slavery, then one needs to ask himself some serious questions.
In some cases  the malicious intent behind the application of blackface was rather clear — as in the case of teens Caitlin Cimeno, Greg Cimeno, and William Filene. These teens, apparently without the guidance of sensibility or political correctness of any degree, thought it appropriate to post pictures to the internet of them dressed as the deceased Trayvon Martin, and his killer George Zimmerman. In a bid to apparently attempt to resemble Martin, William Filene used blackface.
In other cases, the intention of the perpetrators of recent blackface might have been innocent and innocuous, but the effect, as well as the subsequent backlash, was overwhelmingly deleterious.
Regardless of intent, there is a very thin line between tribute and ridicule; blackface, and the painful history which accompanies it, does more than just cross that line — it obliterates it.
As everyone knows (or should know) Blackface, or blackface minstrelsy as it was referred to in the past, was once used as the ultimate contrivance for racial degradation, stereotyping, and outright discrimination. It speaks volumes that people of color remain unsurprised when this occurs almost every Halloween. The outlook on the future, concerning racial sensitivity at least, is rather bleak.
Proponents of the notion that blackface is just innocent fun and people getting offended by it must simply just be ignorant of the facts — that’s what I hope I hope the case is. Unfortunately, as we all know, that’s not always true.
People like Filene and the Cimeno siblings, who dressed in blackface as the killed Trayvon Martin for Halloween, are obviously what the internet would aptly describe as trolls — sad people who do or say despicable things in the hopes of riling up a group of people or generally causing a stir. This doesn’t make it any better though. Using racism as a way to attract attention to yourself might even be more callous than old fashioned racism.
For the many people still baffled by why Blackface is so insulting to black people everywhere, consider this: Is it racist or offensive to dress up as Adolf Hitler, or any Nazi in general, for Halloween? I’m pretty sure you’d agree with me that it is, to an overwhelming degree.
That situation is akin to dressing up in blackface. Hitler and Nazis are now viewed as a symbol of unimaginable levels of hate, oppression, and racism. The same can be said of blackface.
The same way dressing up as a Nazi is disrespectful to all people of Jewish descent, painting your face the color of shoe polish is disrespectful to all black people.
There are much better ways to show tribute to black celebrities; blackface is never okay.