Hip Hop Freestylin’: Shades of Jazz?

The Benjamin Family: Playthell, June, Samori, and Makeda

The Benjamin Family: Playthell, June, Samori, and Makeda

The following is a brief prose-poem about my first live hip hop freestyle jam, an earlier version of which was published in Harlem World Magazine when I served as Editor-in-Chief. Before this culturally somatic wade into the waters of hip hop creativity, I was ambivalent about the form: I appreciated the artistry but had deep reservations about the violent and materialist imagery, the gratuitous profanity, and the way the music industry capitalized on stereotypical and skewed notions of young urban Black American life.

To say I was more than pleasantly surprised by what I experienced would be an understatement—as you will see, it inspired me to get my own rhyme on.


Nearly 20 years ago, the dad, Playthell “Sugarcane” Benjamin, a friend and fellow writer, and the mom, June, a long-time tough and soulful labor negotiator, threw a party-jam on New Year’s Eve for their twin children in their crib at Sugar Hill’s 555 Edgecombe Avenue, where Joe Louis, Paul Robeson, Johnny Hodges, Don Redman, and Charles Buchanan, owner of the famed Savoy Ballroom, used to live. For a time, the vocalist Cassandra Wilson did too, laying down her rust-colored dreadlocks at night, resting those smoky contralto pipes. 

Their son Samori was a budding hip hop manager back then; today he is a graduate of the Columbia School of Journalism and the Sports Director at WBAI-FM in Nueva York. Today, their daughter Makeda is an exercise physiologist, sports scientist, nutritionist, and sacred chi energy practitioner who, back when this New Year’s Day revelation of consecration dropped, was earning high grades in the hard sciences by day; by night, she choreographed, melding everything from jazz to salsa to hip hop. She’s still dancing up a storm.

I remember the boom-t-bap occasion like it was yesterday . . .

Showdown in the Round

Samori Benjamin and Makeda Voletta, who celebrated their birthdays earlier this week

Samori Benjamin and Makeda Voletta, who celebrated their birthdays earlier this week

After “Happy New Year!” we danced until 3 am, when someone shouted: “Drop the beats!” A mood of expectation and anticipation arose, especially among the younger folk. No doubt, hip hop was their soundtrack, their generation’s expressive sense of freedom in form. Three free-stylers gathered together in a circle in the large dining room of the beautiful apartment overlooking Edgecombe Park, with 409 Edgecombe, yet another famous landmark, visible in the distance as the full moon smiled, beaming warmth and welcome.

As this was my very first live cypher, I was light-headed, hazy. Though I was a teen when hip hop came on the scene in the late 1970s, my passions and attention were centered on another Black art form. See, I’m a straight-ahead jazz-man, moved by the grooves and tunes of the cats, the giants—talkin’ about the classic writers of the American songbook, ‘bout Hawk and Pres, Bird and Diz, Duke and Strayhorn, Monk and Max, ‘Trane and Miles, Brownie and paterfamilias Pops. Yea, it’s like that: hard and smooth, cool and silky, rough and crusty, with big round tones derived from Frederick Douglass’s Aunt Hester’s moans.

If you don’t know/shouldn’t have to ask/if you wanna flow/take off dem damn masks

The show down/throw down in the round began. Taking turns in spotlight were Alex Selsis’ rich imagery and philosophic content for the crown, whuppin’ upside da head; Jonathan Holland, spittin’ visceral insults to throw off guard, rhythmic intensity heard all the way to Barnard; and Tiffany Attiles, softer timbre hiding biting wit, aiming to split the two dudes into Reese’s pieces.

Said to myself: Damn . . .

Rhyme after rhyme, drop of a dime Speaking in rat-ta-tat-tat tongues/no need of interpretation/conflagration Scattin’ with sense syllables, scribbling at home/dropping antagonistic poems on domes

But it wasn’t just combative.

Cooperative too/in the groove Onlookers co-signin’ the rhymin’ Word playas diggin’ their comp’s stylin’ Not taking the dozens to heart/inside idiom wisdom to impart

It reminded me of what jazz jam sessions might have been like back in the day, cats cattin’ on their horns, blowing sweet and steep, inspiring a child to be born.

Maybe they played at mid-tempo, deep in pocket, healing the sick, going to the territory, like J Dilla laying down beats for Black Thought to style freely. Or so blindingly fast that you marveled, like the Flash versus Jessie Owens; like the speed of double timin’ Busta Rhymes memetically mediating Charlie Parker and Clifford Brown blowing “Cherokee” changes; like Nas and Rakim bending ear to the splendor of Jon Hendricks’ vocalese classics “Freddie Freeloader,” and “Joy Spring.” Like Queen Latifah pointing the way back home as Dana Owens, swangin’ with Christian McBride, crooning “Lush Life” on the Grammy Awards, landing in the blues as Bessie Smith.

QueenLatifah_HBO-as-Bessie.jpg

Harking back to the ring shout/no doubt Cultural continuity/fluidity Universally particular/Cosmos reticular When there’s no prying gaze? these young folks amaze

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Clifford Brown’s “Joy Spring”: Jon Hendricks’ Vocalese Genius

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Beyonce and the Power of Myth