While A.E. Housman's life is being meditated upon by one of the theater's preeminent playwrights uptown, the life of a wordsmith of a vastly different stripe, the rapper Tupac Shakur, is the subject of a surprisingly similar play by a promising newcomer downtown.

While A.E. Housman’s life is being meditated upon by one of the theater’s preeminent playwrights uptown, the life of a wordsmith of a vastly different stripe, the rapper Tupac Shakur, is the subject of a surprisingly similar play by a promising newcomer downtown.

As Tom Stoppard’s “Invention of Love” does for Housman, Michael Develle Winn’s “Up Against the Wind” investigates Shakur’s life in a semi-surreal, playfully theatrical manner; like the Stoppard play, it attempts to assess a life through the prism of the culture that shaped it; it, too, takes the theater audience to unfamiliar places and speaks in unfamiliar tongues.

The expletive-splattered street slang that Winn scrupulously re-creates is, truth to tell, a language no less arcane to most New York theater audiences than classical Greek and Latin, although in Winn’s creative hands it is a very living language indeed.

Rosemary K. Andress’ vigorous, visually poetic production opens with a simulation of a rap concert. Seconds later we are in a police station, where Shakur is being arraigned for rape; the strange poles of Shakur’s life — and those of many other rap luminaries, as one deduces from the recent trial of Sean “Puffy” Combs — are thus neatly defined. Even as he is surrounded by the spoils of celebrity and overwhelming financial success, Shakur’s life is still mired in violence and uncertainty.

With a sharp ear for vernacular speech and a no less sharp, zesty humor, Winn humanizes his subject without glorifying him, and offers various outside points of view as well.

Scenes between Shakur and his family, friends and associates alternate with monologues delivered by ancillary characters led by his mother Afeni, played with commanding force by Hazelle Goodman.

There are also comically depicted news reporters giving updates on the proceeding trial, and monologues from listeners whose lives were affected — for both good and ill, Winn suggests — by his music.

The need to convey information and to evenhandedly describe the cultural milieu that shaped Shakur’s life — the media backlash against the violence and misogyny in rap lyrics, for example — mean that Winn’s play has some plodding and extraneous patches, and occasionally the earnest tone of a TV docudrama (this is particularly true in contrived encounters between the cop and Shakur that come off as tidy debates about the plight of black youth today).

But most sequences are flavorful and compelling, infused with the urgency of Anthony Mackie’s fiery performance in the central role and enlivened by the vivid work of the supporting cast.

Hot-headed, cocky and potentially violent when his achievements and his potential are in question, Mackie’s Shakur can be amiable and loose when he’s hanging with his friends.

The anxious way he clears the room of pot smoke when his mother arrives unexpectedly takes on a sad poignancy when we learn that Afeni is herself addicted to crack.

Mackie is onstage for most of the play, and the potency, variety and sensitivity of his performance never flags. Like playwright Winn, a recent graduate of Juilliard, he’s an impressive young talent.

So, too, is director Andress, who orchestrates the play’s complex narrative with skill and style. She is aided by some exceptional work from set designer Narelle Sissons and lighting designer Peter West, whose seamless collaboration comments on the harsh contrasts in Shakur’s life. The stark solitude of a prison cell is evoked as convincingly as the rhapsodic hedonism of an urban nightclub.

Jonathan Sanborn’s varied, moody music score also helps set the scenes.

In the second act the play’s mood turns unremittingly dark as Shakur allows anger and resentment to consume him. Convicted on the rape charge, Shakur watched his album climb to No. 1 from a prison cell.

His record company, Interscope, led by Jimmy Iovine, caricatured here as a canny white exploiter, refused to post bail as his appeal went through; Suge Knight, the thuggish chief of Death Row Records, whose overtures Shakur had previously resisted, finally earns his loyalty — or more accurately his indentured servitude — by coming to his rescue.

Numbness sets in as we begin to see that the rhetoric of Shakur’s world — the unvarying references to women as “bitches” and “hos” and men as “nigaz,” the vivid epithet beginning with the word “mother-” attached to anything and everything — is not just linguistic rebelliousness but a symptom of a soul-destroying nihilism that it seems impossible for Shakur and his kind to shake.

The play cannot really get at the myriad factors that create this poisonous landscape, although it does point toward some of the usual suspects: absent fathers, working mothers, bitterness born of an impoverished childhood.

“Up Against the Wind” ends with both Afeni and the late Shakur, felled at age 25 following his second encounter with a spray of bullets, offering lyrical monologues redolent of redemption. They sound self-conscious and hollow in view of what has come before.

The play’s achievement, in fact, is in its ability to vividly render a world in which issues of good and evil, and black and white, are never as simple as they seem, and the power of words isn’t great enough to change the world’s ugly truths.

Up Against the Wind

New York Theater Workshop; 188 seats; $45

Production

A New York Theater Workshop presentation of a play in two acts by Michael Develle Winn. Directed by Rosemary K. Andress.

Creative

Sets, Narelle Sissons; costumes, Olu-Orondava Mumford; lighting, Peter West; music, Jonathan Sanborn; sound, Jerry M. Yager; dramaturge, A.T. Amicarella; production stage manager, Jason Scott Eagan. Opened April 2, 2001. Reviewed March 31. Running time: 2 HOURS, 20 MIN.

Cast

The Girl/LeeLee, etc. - Olubunmi Banjoko Record Store Clerk, etc. - David Brown Jr. Suge Knight - Kevin Daniels Afeni Shakur - Hazelle Goodman Ed Gordon, etc. - J.D. Jackson Booker, etc. - Nashawn Kearse LaDonna etc. - Tracey A. Leigh Tupac Shakur - Anthony Mackie Jerome Perez - Jesse J. Perez Prison Guard, etc. - Christopher Rivera Jimmy Iovine - Joseph Siravo Sekwiya Shakur - Tracie Thoms Lt. Dan - Isiah Whitlock Jr.
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