At the Brooks Brothers Hip-Hop Summit | HumorOutcasts

At the Brooks Brothers Hip-Hop Summit

January 5, 2018

 In recent years, rap kings such as Jay-Z and Diddy have displayed their swagger with looks that were more boardroom than bling. 

                                                              The Boston Herald

Image result for 75 state street
75 State Street

I turn my collar up against a stiff breeze off the Atlantic as I hit State Street, ground zero of hip hop fashion in Boston.  It is here that a Brooks Brothers store sits hard up against a gritty row of pizza joints and copy shops, a forlorn attempt to make a silk purse out of a sow’s ear of a neighborhood where life is as cheap as a Jos. A. Bank polyester tie.  Men have killed here–in cold blood–to get what I’m after.  I don’t want to be a victim.

I scan the street, looking for signs of rap posses from rival gangs–the Blue Hill Ave Mob, the Melnea Cass Krew.  The coast seems clear, but things can change in a second on the mean streets of Boston.  Today is the biggest day of the year on the hip-hop calendar; its the After Christmas Sale at Brooks Brothers, when dorky but expensive men’s wear gets marked down to prices that are to die for.

The coast seems clear, and I edge my way up to the store’s brass-plated doors; they’re locked, and won’t open until ten o’clock.  I stake my ground as the first person in line, and pat my pocket to make sure everything’s in order; a Starbucks blueberry scone to sustain me, a $100 Brooks Brothers gift card from my in-laws, and my “piece”–a fully-charged iPhone I can use to keep track of my emails and signal my wife for help if somebody tries to bust a cap on me.

Image result for vineyard vine tie


A few stragglers–”corporate” types–line up behind me.  I recognize an auditor from a Big Four–or is it “Big Three” today?–accounting firm, wearing a two-button blue chalk stripe.  “Dog–that is so ill!” I say, and he gives me a nod.

“I’m likin’ your Vineyard Vines,” he replies, pointing to my pink tie festooned with little white whales.  “That is so ‘crunk’.”

“You know me,” I say.  “I’m a huge Melville fan.”

Image result for melville herman
Herman Melville, a/k/a “Big Whale”


We reminisce about the old days–how we used to be able to pick up two 100% cotton button-downs, a tie, maybe even a cable-knit cardigan sweater with the goofy-looking shawl collar without risking life and limb.  The streets were peaceful before the gangsta rappers muscled in on the boxy upper middle-class looks we favor.  You could grab two or three suits off the rack on sale days, take them back to the dressing rooms without incident, try them on at your leisure.  Today, if you tried to pull dat shit, somebody stomp you with their Timberlands and grab the herringbone three-piece.

Lost in our sentimental reverie, we don’t notice when the Humboldt Street Pimpz arrive.  Their tricked-out Volvo station wagon escapes our attention as its inner city accessories–spinning rims, whistle tips and suction pipes–blend like protective coloring with the prep school and college stickers on the back window.  They park–illegally!–in front of the store, and approach from up the street.

Image result for beat up volvo
Phat ride.


The gang’s leader–or “chubby doctor” in hip hop slang–is J-Dee, a lawyer wannabe who crapped out in first year Constitutional Law and ended up selling drugs to his former classmates.  He and I have had a beef going way back to when I wouldn’t let him borrow my yellow highlighter during the lecture on Marbury v. Madison.

“Looks like we’re first in line,” he says with a disingenous grin, showing off his “grillz,” precious metal orthodontic devices that are nothing more than a fashion accessory.

Image result for grillz
Nelly’s a Cardinals fan–like me!


I look him straight in the eye.  “You don’t know the pain my sistas went through to get straight teeth,” I say, trying to control the emotion in my voice.  “Den you come on with dat shit.”

J-Dee looks back at his homeys and emits a little snort.  “Dis’ pussy ass waffle puffin’ punk is talkin mumbo jumbo,” he says.

“Hold on Dee,” Em-BA, one of his posse says.  “I think you misused the term ’mumbo jumbo.’”

“I did?”

“Yeah,” Em-BA says.  He checks his iPhone, and he goes on-line to a hip hop slang glossary.  “It means ‘spoken lies during a business transaction’.”


“So–we ain’t transactin’ no business yet!”

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From Tha Bitches and Hos Dept.


J-Dee looks me up and down.  I can stand his mean-muggin’.  “Why don’t y’all go back to the ‘hood and leave the WASPy, preppy look to us?” I say in as stern a voice as I can muster.

J-Dee isn’t fazed.  “Brooks Brothers is classic, ponk,” he says as he fingers his repp tie.  “You buy sumpin’ here–it never goes out of style.”

I should have known that a threat posture wouldn’t work with this crew.  I change my motivational tack, and “come about” into his headwind, as we say down at the Hyannisport Yacht Club.

“You know, you should really go for a more tailored look to show off those guns,” I say, referring to the biceps he built up during a six-month sentence at MCI-Norfolk, the medium-security prison I pass on my way down to the Cape.  “Brooks Brothers shirts are cut to be very blousy–almost like a spinnaker,” the balloon-like sail used when sailing downwind.

“You wanksta,” he says with contempt.  “I use those full-cut Brooks Brothers oxford cloth shirts as a Lackalacka Moomoo.”

“What you talkin’ about?”

“Shows how much hip hop slang you know,” he sneers.  “That means a big-cut shirt you can hide your piece under.”

He’s won this round, and I back off.  It’s just as well, because the store manager arrives to open the front door, touching off a mad scramble for knock-off British public school jackets that scream “I’m a doofus!” to tha ladies.

Image result for brooks brothers british school boy jacket

I hang back, knowing exactly what I’m looking for.  Like Jason of the Argonauts, I’m on a quest for a Golden Fleece; a necktie with the Brooks Brothers crest, a sartorial talisman that will mark me to the world as someone so insecure I not only pay the chain’s premium prices, I advertise for them as well!

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“We met the nicest young chap downtown today–he said neck tattoos will be all the rage this year!”


I make my move and am about to pick up a boring maroon cravat when I feel the cold hand of death upon mine–it’s J-Dee.  He wants what I want–we can’t both have it.

I turn around and realize the Pimpz have me surrounded.  I couldn’t get away to the men’s wear department at Talbot’s now if I wanted to.  My life–such as it was, shuffling papers, sending emails, yapping on the phone–flashes before me.  I stifle a yawn–was it really that boring?–then speak.

“Dee–have a heart man,” I say, my voice cracking.  “You must have more ties than Celine Dion has shoes–let me have this one.”

He laughs a mirthless little laugh.  “Why should I?  You got no street cred!”

It’s my turn to snort at him.  “How old are you?” I ask.

“Like Bo Diddley once said,” he replies, “I’m just twenty-two, and I don’t mind dyin’.”

“Man, I was rappin’ before you were born!”

“You were?” he asks, incredulous.

“Yeah,” I say.  “Back in the 80′s when the water started rising in the Back Bay, I put together a track with a borrowed beat ‘cuz I was worried about my oriental rug collection.”

Em-BA is suddenly all ears.  “Lay it down for us, dawg,” he says.  “I got a coupla Shiraz’s myself.”

Image result for oriental rug

I clear my throat, then launch into the lyric that catapulted me from obscurity to opening act for Grandmaster Flash on his “Corporate Jungle” tour:

The Back Bay’s sinkin’
And I be thinkin’
Won’t be no joke
If my rugs get soaked.

I scan J-Dee’s face for some hope–some kind of sign.

“Go ahead and take it,” he mutters with grudging respect.  “You and dat tie–you both old school.”

Available in Kindle format on as part of the collection “Our Friends, the Rappers.”

Con Chapman

I'm a Boston-area writer, author of two novels (most recently "Making Partner"), a baseball book about the Red Sox and the Yankees ("The Year of the Gerbil"), ten published plays and 45 books of humor available in print and Kindle formats on My latest book "Scooter & Skipper Blow Things Up!" was released by HumorOutcasts Press last year. My humor has appeared in The Atlantic, The Christian Science Monitor, The Boston Globe and Barron's, and I am working on a biography of Johnny Hodges, Duke Ellington's long-time alto sax player for Oxford University Press .

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