[This blog post was provided by the author Jim Shorts. You can learn more about him and download his free ebook and white papers at gustosmooth.com]
I’ve had the opportunity to observe the Obama family in person celebrating Halloween. Like other holidays as well as regular days, Halloween in the Obama White House is a fucked up event.
Barack is an avid cross-dresser and loves pretending to be someone he’s not. Thus, Halloween is his favorite day of the year. One year he dressed up as Steve Urkel. Last year, he wore the same costume as Michelle did – they both dressed up as Grace Jones. That was awkward. I will say, though, that President Obama is surprisingly agile in high heels. He must get a lot of practice wearing them.
Mrs. Obama doesn’t get into the holiday as much. She gets discouraged easily, because it’s hard for her to find costumes that fit her broad shoulders as well as her broad behind. I have suggested to her that she dress up as former professional fighter Trevor Burbick. I think she could pull that off.
Marian Robinson, Michelle Obama’s mother, always dresses up for the occasion. In previous years her Halloween costumes included Nell Carter and Della Reese, and one year she wore white-face and claimed she was Archie Bunker.
Two years ago, the White House Halloween party had to be cancelled because of her. Back in 2012 ‘Mother’ Robinson couldn’t decide who to be for Halloween. The always witty Vice President Joe Biden suggested she dress up as Aunt Jemima. Mr. Biden himself was already in costume as Casper the Friendly Ghost. Marian Robinson, who can not take a joke, told the Vice President to “put on a got-damn pillowcase and let his inner Klansman come out and play.” Mr. Biden punched her in the mouth, and in the ensuing melee Secret Service agents discharged so much pepper spray we had to cancel the party.
As for the Obama children, their lack of personality sabotages whatever costumes they choose. I will say, though, that Sasha does look very convincing when she dresses up as the ambiguous Willow Smith. Malia usually just mopes around.
Obama Halloween parties are pretty lame. Barack plays a game called “bobbing for plums.” He is great at it and always comes up with two plums in his mouth at once. It’s a game he says he learned from colored actor Don Cheadle. I’d never heard of it before. Michelle pretends to act like a normal mom and passes out toothbrushes to the children of White House staffers during the mandatory trick-or-treat. The Obamas manage to take the fun out of just about every day, including Halloween, and most of us are glad when it’s over.