Bob Marley & Anna Wintour Exposed! The Lost Halloween Night Edition

“She was “riveted” and acted as if she’d “met God,” one friend tells Oppenheimer, who reports she “virtually disappeared for a week” while notorious womanizer Marley was in town, spending all her time backstage. “When Wintour finally resurfaced, she looked utterly worn out from her exertions with the rasta legend, but denied to friends she’d spent the week in Marley’s bed. Pals didn’t buy it and assumed she merely wanted to keep him to herself. “

Page Six.

Bob was excited to be back in New York City. His one millionth joint didn’t prove to be any more of a downer than his several sold out shows he had scheduled all throughout the city. This feeling was better than being fired off a tour by Sly and the Family Stone for “hogging up all of the adoration”  or the Germans naming a car the BMW after “Bob Marley and the Wailers”. This feeling went deep into his loins, like the tingle a child gets after his first wet dream. This was Bob – in lust – with someone he would have never imagined he’d ever be in the same room with. A woman as powerful as she was sexy – a lion in a paper cage who was ready to pounce and maul an entire industry at the first sign of rain on her Manolos. He was having a secret rendezvous with the Athena of modern day fashion: Anna “The Ice Queen” Wintour.

Anna had a reputation to keep. She couldn’t be seen running around town with some Rasta-ruffian lead singer from the other side of town – or the ocean for that matter. Those are things you did after your 5th Mai Tai on a resort where you get those stupid beads in your hair, not in NYC. She was a woman of high powered couture and a low tolerance of flaws.  She was the heralding editor of the most powerful fashion magazine in the known universe and her power to make or break a brand or model was legendary. Designers groveled on the asphalt she walked on while models played intern to her madness and succumbed to her every whim. This was a woman who got as many marriage proposals as she did resumes. A diamond without the need for the rock, London had definitely unleashed its weapon of mass destruction on a concord jet and 9/11’ed 5th Avenue.

She gave her assistant an itinerary, and then gave her trusted friend the real one. She had her many minions believe she was going somewhere exotic to look at some new designer that was begging for the mercy of her eyes when in fact she was going to a small 1 bedroom apt in Brooklyn. She couldn’t risk a 5 star hotel or a no star hotel because he was Page Six fodder and everyone read the Post. Her trusted friend was instructed to leave her finest fur and a copy of the new November issue of Vogue at the cramped lower class abode and to leave the keys with the bodega on the corner. She couldn’t afford to be seen with her, or anyone for that matter. She was going out with Mr. “Bob Morley”, and she wanted him all to herself. It was Halloween that Sunday, and everyone was going to be in costume – they could go out as themselves and nobody, not even the all seeing eye of Page Six, would notice.

Bobs first stop was at a trap house in the Lower East Side of Manhattan. Everyone there was readying their “party favor” shopping list for a night of impossible to recall wickedness. The blonde temptress that owned the apartment opened the door with her sexy smokers’ accident and her just got out of bed East Village  hotness.  Bob was shocked to see his good friends M***, and S*** already comfortable and pre-partying it up.  They all trade pleasantries and hug like explorers just arriving home from an expedition.  They ask him about his manager, who they had read in the local tabloids had been robbing him. Bob refuses to mention Don Taylor by name, only stating that most of his money is tied up now and “dem no worry we” due to the fact he beat him within a inch of his life.  They ask him about his family life, Bob laughs proclaiming he’s glad he’s not an American citizen because with his 20 plus kids and child support he would have killed his manager. Exchanges are made and handshakes are given and they all agree to meet later on that night.

Bob and Anna meet at the Lorimer L train station in Brooklyn. They assumed no one would ever suspect them on a train. Every car service in New York had trained their eye to spot and report whatever Anna was doing and Bob’s rising star was shooting through the stratosphere like a meteor. Two of the biggest stars in media on a pheasant train? Who would imagine? The local yokels with their vintage fair and their fresh from Tennessee smell knew none the wiser. Everyone thought Bob and Anna’s costumes were “ironic” and while the older “hipsters’ didn’t bat an eyelash the younger “I just moved to Brooklyn to slave at being cool” crowd hooped and hollered and offered high fives like they were free AM New York newspapers.  Bob and Anna didn’t mind, Bob was still catching a contact high from his clothes and Anna was already hype off the disco dust that was in Bobs tiny jean pocket. Also they weren’t in love; that was for their respective families and people they lie to – they were in LUST – an all consuming emotion that could only be described as a mongoose and a cobra locked in a cage for a death match.

They followed the West Village Halloween Parade around 20th street and 6th Avenue then made their way down to West 4th Street. Besides the actual marchers with the elaborate group costumes and creative floats blasting the dance music of the day, the streets where littered with the underbelly of New York’s “classiest”. From the project mom with 7 kids in tow all wearing half costumes to the NYU undergrad flasking some trust fund whiskey in her smuttiest get up. Fraternity brothers and their “I just blew my credit limit” on storm trooper outfits to thugs and criminals on the run from police who would be hiding on any given day except that today it was normal to walk around with a hockey mask. Black butchy lesbians who you would think were wearing a “hot rapper of the day” costume sexually harassing Puerto Rican girls doing their best “slutty bumble bee” impression. The night had the frenetic pace of an oil and water milkshake. By the time they had reached Christopher Street neither Bob nor Anna wanted any part of this fiasco. Anna claimed she hadn’t been around so many poor people since that one time NYC had a black out and she had to take the stairs from her offices at Conde Nast.

They make a quick left off Bleeker Street and have a quick drink at Delicatessen. By then Bob’s cell phone starts to go off with all sorts of party invitations demanding his required presence. Already intoxicated by Anna’s snobbery and her sheer black stockings, Bob started thinking of uncharted parts of the city in where he can tear them off with his ganja stained teeth. He makes a sexual joke about banging his balls against the paddle of her ass: because he’s a great ping pong player. She tells him she was hoping something along the lines of a tennis ball banging against her racket: because she has a thing for Roger Federer. They look at each other awkwardly -giggle- kiss like teenagers in a backseat of a lemon – and decide to go to a loft party in Chinatown instead.

Outside of the packed event was the collective of underground nightlife and graffiti goons known affectionately by Bob as “The Peter Pan Posse”. They were trying to rush the door of the party but the crowd was too dense for anyone to get near Ian, the overwhelmed but tragically cool door guy. Someone jokes to Anna that she could get a prime seat at the US Open but couldn’t get into this party.  Bob sneers at the “bro”. Anna just offers her trademark icey stare and the patience of a tarantula. Being that she really couldn’t blow her disguise – as herself- she does something no one would ever suspect the real Anna of doing: SHE WAITS IN LINE. Bob – happy to be around his NYC crew – starts hopping around and skanking like he was doing a parody performance of himself. The both of them are lost, officially mocking themselves on cc  tv.

Bob spots S*** and “Captain Black in America” smoking what looked familiar but smelled oddly chemical and without haste he steams it till the ashes hit his lips. A total lack of better judgment on his part. By the time Anna got the ok to walk pass the unpopulars waiting in line, Bobs Peter Pan partners had peeled off in a Masserati  and…

everything started…

to go..



Bob had just cropped dusted himself.

When he finally snapped out of his walking coma, he was surrounded by his friend T**** and his S**** crew family. They all looked like wrestlers which confused the re awaking Bob. Anna was in good spirits but a little annoyed by Bob’s walking nap.  In true Wintour fashion she demands a drink and Bob starts jamming his way towards bar. It’s a full time job for him to hold his surrounding reality together as all the costumes start to disorient his already smothered brain cells. He finally finds a spot near a reptile and orders.

“Ya mon, me gwan need dem two jaques of de rocks..”

“Excuse me?”

“Bombo rast me need dem two jaques on de rocks!”

“Oh, I’m sorry; you don’t have to stay in character the entire time “Bob”. Here, that’ll be 24 bucks”

Bob rolls his eyes and beams a confident smirk, the one that got to warring faction of Jamaica on stage and made them reach a peaceful accord, and goes for his wallet…

He checks the front pockets.

Then his back pockets.

Then all of the pockets on his jacket and shirt.

He repeats this 3 times.

“Yaaaaaaaaaaaaaaaaaraaaassssssssst me lost dem boma clot wallet wif mi money Jah man wha fuckery in Babylon!!!”

(Photo provided by Nick Gallo)

Bob, in his dusted haze, lost over 500 dollars. Anna sensing Bob was taking too long goes to bar to find a Tasmanian Devil of dreadlocks in a tizzy. “Don’t worry darling, I’ll take care of this” she said, rubbing her fingers on her black Amex like it was the finest of silk. “I’m not used to taking care of men this way, but for you I’ll make an exception.” She then rubs her hand over his crotch and whispers “mmmmm feels like The September Issue…” and closes her soft lips around the tip of his earlobe. Bob closes his eyes and responds “girl flex, time to have sex…” but before Anna can respond they are whisked away to Kenmare where they find the Peter Pan gang and S*** in the exact same predicament Bob was in earlier. The walking nap was huge that Halloween.

After countless hello’s and getting highs in New York’s answer to the now defunct Beatrice Inn, Anna decides she’s over the fake disco and indie rock being played and decide she wants to hear some Morrissey at Sway lounge way over on the west side. Bob thinks she wants to leave because someone else showed up to dressed as her and she didn’t want her cover blown. She reminds Bob that he doesn’t like this music either and that he’s just too wasted to realize it. He laughs and as they get into a taxi he goes into this rant:

America is pure deviltry, dem t’ings dat go on there. Dem just work with force and brutality. Dem lock out the punk thing because they see something happening. So the oppressors bring another man to blind the youth to the truth, and dem call him-John Tra-vol-ta.”

This makes Anna’s pussy moist to the point it ruins her Agent Provocateur gifted panties.  After a brief accidental meeting with the emperor of Zamunda  and a few rolled up brown sticks of illegal gardening power Anna and Bob escape into the night to the tune of Morrissey’s “International Playboy”. They have their last drink around 6 am on the Rooftop of FatBaby on Rivington Street surrounded by people who the last thing they need in their life is a mention in Page Six. One of them organizes a car for them to take them back to their one bedroom love den in Brooklyn. Free to be themselves, they fucked in a fashion that would only rival a David la Chappelle photo shoot or something you could only do if you possessed Terry Richardson’s little black book. The apartment wasn’t big enough for their carnal desires so every inch of wall was covered in musty and illegal in several states lust. They collapse on a hardwood floor littered with dirty laundry and broken furniture. They order in using Spanish accents. Their only thought being “how do we explain this mess?” and “how do we leave here unnoticed after that?

Happy Halloween guys.


4 Responses to “Bob Marley & Anna Wintour Exposed! The Lost Halloween Night Edition”

  1. lol – some of you guys really need to listen to yourselves

  2. lol – some of you guys really need to listen to yourselves

  3. […] erotic companion of Bob Marley over 30 years ago. Rumors have long circulated of their unique and salacious companionship that crossed significant borders–national, racial and erogenous. Anna is […]

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