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The fall of 2009 saw something of an apotheosis for Chicago theater. Following in the wake of Tracy Letts’s Pulitzer-winning August: Osage County—an epic family drama in the grand American tradition of O’Neill, Miller and Williams—a pair of plays set in Chicago’s Uptown neighborhood opened in Times Square. Keith Huff’s A Steady Rain, a generic police procedural enlivened by the Hollywood wattage of Daniel Craig and Hugh Jackman, currently occupies a Manhattan theater across the street from Letts’s latest work, Superior Donuts, an updated Chico and the Man set in a Sheridan Avenue donut shop. Meanwhile, Chicago-based director David Cromer continued his string of restagings of American classics: his accolade-laden Our Town, still drawing an audience Off-Broadway after almost a year, was followed by a production of Neil Simon’s Brighton Beach Memoirs. Though the latter suffered a premature death, the blow was softened by news of Cromer’s forthcoming version of William Inge’s Picnic. The phenomenon even caught the attention of Time magazine, which recently declared a Chicago pedigree de rigueur for straight—i.e. non-musical—plays hoping to hit Broadway. (Less happily, Time’s Richard Zoglin construed the “straight” in “straight play” in true lunk-headed fashion, attributing Chicago’s success in part to a dearth of heterosexual playwrights in New York.)

While this attention is welcome, it nonetheless helps reinforce some timeworn stereotypes about the city’s theater. As epitomized by Steppenwolf Theatre Company (Letts is an ensemble member), Chicago stages play host to gritty, naturalistic, actor-driven drama. Even the highly stylized work of David Mamet, the scene’s ultimate success story, eschews the cerebral traditions of modern European theater—Pirandello, Ionesco, or for that matter Tom Stoppard—in favor of profane confrontations among street-smart, physically active loudmouths.

But another strand of Chicago’s theatrical tradition, more aesthetically adventurous, blends the populist energy of the storefront scene with the kind of sardonic and omnivorous intellectuality associated with such University of Chicago offshoots as the Compass Theater and Second City. Moving nomadically from loft space to café a step or two ahead of the onslaught of gentrification, this fringe tradition has given rise to a number of redoubtable troupes and gifted performers. Few companies, though, can boast the record of accomplishment and lunatic invention enjoyed by Theater Oobleck, initially formed by fellow students at the University of Michigan and notable for its egalitarian no-director policy and longtime practice of pay-what-you-can pricing. Oobleck is now in its twenty-first year of producing adaptations of Lacan (2006′s The Purloined Letter), scabrous satires of the Committee on Social Thought (last summer’s Strauss at Midnight) and the prolix, teasing work of Mickle Maher, one of the finest playwrights at work anywhere today.

Audiences last fall had the rare opportunity of seeing Maher’s 1999 An Apology for the Course & Outcome of Certain Events Delivered by Doctor John Faustus on This His Final Evening in a tenth anniversary production. The piece, a monologue delivered by the legendary doctor under the titular circumstances and witnessed by a silently malevolent Mephistopheles, displays many of the hallmarks of Maher’s writing. Blending lyrical melancholy with sharply absurdist wit, the play hunts avidly after the conditions of significant action and utterance even as it toys with the possibility that none exist. The play’s central conceit concerns the diary that Faustus has kept during the decades of his infernal bargain; madly, in order to thwart the demon’s interest in reading his most intimate thoughts, the doctor has resorted to inscribing nothing but random groupings of hatch-marks in his book. In the course of simultaneously justifying and decrying his innovative solution, Faustus recounts the clownish interactions between himself and Mephistopheles, meditates on the nature of evil and memory, and dreamily recollects the strange vistas that his contract has afforded him:

Back a hundred millennia. When language was ridiculously complex, when it still hadn’t stripped itself down to the bland, serviceable thing it’s become in our centuries. When tribes in imitation of the slowly advancing glaciers surrounding them spoke a language of only one word, a million syllables long, whose utterance began at birth, improvisationally, with the first syllables and ended at death with the last. A whole lifetime huddled on the ice, speaking—just once—a meaningless word. Meaningless: there was only the one word, no others to define it. And if there had been a definition, who could’ve lived long enough to speak it? Faustus was there. He heard nonsense spoken as a life-duty. A commitment to nonsense one million syllables long.

One can see encapsulated in this passage not only Maher’s passionate engagement with language at diverse levels— from the rhetorical mastery of syntax and cadence to the semantic wizardry of words, their ability to conjure habitable worlds out of bare ice and air—but also two of the issues that drive Maher throughout his various theatrical follies. There is the idea of the impossible or meaningless project as not just an intellectual limit or an aes- thetic curiosity, but an ethical necessity: a “life-duty.” And there is the sense of inescapable loneliness heightened by the attempt to communicate, as though the fundamental ethical task is to make one’s own singularity intelligible and thereby transcend it—a task which in Maher’s universe seems inevitably doomed to failure.

The atmosphere of eccentric urgency that suffuses Faustus’s monologue is only intensified in the recent production by the masterful performance of Colm O’Reilly as Faustus, ably and unnervingly supported by David Shapiro’s silent Mephistopheles. Sad- eyed and broad-shouldered, O’Reilly has the uncanny ability to suggest clouds of thought separating himself from his own words, not to mention the ever-receding audience. His oddly cadenced diction is reminiscent in its slurred precision of a young Orson Wellescrossed with the murkily heartfelt remove of The Rolling Stones’ Exile on Main Street. Both his voice and his seemingly casual yet indelible gestures manage that elusive theatrical trick of achieving maximal expressiveness even as the meaning and the man behind the expres- sions remain veiled.

The intimate familiarity with which O’Reilly handles Maher’s text reflects the close working relationship that the pair have developed over the past decade. The protean actor has appeared in virtually all of Maher’s Oobleck productions. He played Quasimodo in 2001’s The Hunchback Variations and eerily impersonated PBS anchor Jim Lehrer for The Strangerer in 2007. Each of these recent plays continue and intensify Maher’s tactic of high/low juxtaposition even as they replace Faustus’s monologue format with such quasi- theatrical genres as the press conference. In Hunchback, Beethoven and Quasimodo hold forth in a series of blackout scenes on their failed attempt to produce the sound called for in Chekhov’s directions for The Cherry Orchard, while The Strangerer—inspired by Camus’ The Stranger—details George Bush’s repeated attempts to murder Jim Lehrer during a 2004 presidential debate.

In the latter play, Oobleck regular Guy Massey portrayed Bush as an uncanny blend of homicidal drive, tangled syntax and haunting loneliness. Massey also took the lead in what is perhaps Maher’s most accomplished piece, Spirits to Enforce (2003). The initial production of this play, a fundraising telethon featuring phonebanking superheroes that gradually morphs into an exquisite staging of The Tempest, assembled a clutch of the city’s fringe talent: joining O’Reilly, Maher and Massey were writers and performers including David Isaacson, Dave Buchen and Kat McJimsey, all of whom have long-standing ties to Oobleck. The play’s technical complexity and wit are immediately apparent. Featuring triple roles for each of its performers— superhero, secret identity and Tempest character— Spirits to Enforce unfolds as a series of overlapping one-sided phone conversations, from which it emerges that these heroes display a bemusing range of powers. Craig Cale, a.k.a. the Pleaser, avers that there is “no corrective more effective than a pleasant conversation”; the Bad Map, constantly tripping over her dead cat, subjects others to her pervasive fog of confusion; the Snow Heavy Branch, played by Maher, presents a haiku come to life as he bemoans the unpopularity of his gondola.

Though cobbled out of comic-book scenarios and Shakespearian quotations, the play attains a mysterious, heart-stopping beauty. In its climactic moments, the heroes rec- ollect the performance of their Tempest before an audience of super-villains, led by the dastardly Professor Caliban, who takes on the most villainous role of all: theater critic. In the course of their recollections, the performance almost miraculously shifts from one remembered to one enacted before our eyes and ears. The moment epitomizes Maher’s work in two ways. It plays powerfully on the dubious temporality of theater, thematizing the status of its events as both imagined and present, here and far away. And it reflects his constant awareness of theater as an art form still willing, despite and perhaps even because of its cultural marginalization, to make the largest possible emotional and intellectual claims. Forcibly freed from the distorting effects of financial and cultural capital, fringe theater accrues an imaginative freedom that allows it to puncture contemporary façades of respectability. In effect, Maher melds the deflationary tactics of classical satire with the de-familiarizations of literary modernism, simultaneously exposing the arbitrariness of social convention and hinting at the potent strangeness of the reality thereby concealed. When O’Reilly’s delightfully odd Jim Lehrer, for instance, natters on as imperturbably about his extensive collection of hunting knives as about the elaborate framework of a presidential debate, it ironically exposes the kabuki rituals of our politics and interrupts our settled sense of the world.

Part of what enables Maher to create a theater that successfully functions at a ver- tiginous ontological level even as it remains simply and irresistibly entertaining is his acute attention to discourse and sound. From the extended riffs of Faustus to the intricate group counterpoint of Spirits to Enforce, his plays often work as quasi-musical compositions, busy- ing themselves with the sonic quality of language. He has an unerring ear for the evasions and hiccups of consciousness folding back on itself, whether in Faustus’s intimate confes- sions or the estranged soundstage territory of The Strangerer. George Bush, as one can imag- ine, yields ample material, and yet what is striking about this piece is how empathetically Maher depicts a man lost in language:

There is a way to kill people that does make, will make the whole world cheer. Here in the air. I believe I saw a theatric-causation of that method last night. Here in this great city of, uh, ruined city. DO YOU KNOW THE FEELING OF WHICH I AM IN POSSESSION OF? BELIEVING IN SOMETHING WHICH IS SECRET TO MYSELF EVEN?

This attention to the fundamental elements of stagecraft extends to the question of the au- dience, ever present in a dramaturgy that generally avoids the fourth wall approach of clas- sical drama through such direct-address modes as the monologue, the press conference and the debate. Toward the end of Faustus, we learn that this performance has been conjured by Mephistopheles for Faustus’s benefit: that his final wish before dying is to explain himself to us, “a few random people.” It’s another moment which transmutes the fictionality of the scenario into a living transaction—this time involving a group of strangers gathered in a shadowy basement, facing one another in rows of straightback chairs. Faustus ends the play by walking offstage; Mephistopheles follows him, switching lights off one by one. The silence that ensues has the kind of depth that drowns.