Ingeniously structured and often inventively written, Dan O’Brien’s new play The Dear Boy is like a novice magician’s attempt to perform two classic tricks at once. Naturally, neither one comes off. Concentrating on either one and leaving the other aside might have given the audience a sense of the trickster’s skill; this way he just looks confused. Which is too bad, because inside the muddle a lot of feeling and intelligence are waiting to escape, like the rabbit hidden inside the magician’s top hat. No bunny, alas, gets produced here.
The confusion starts with the characters. One of O’Brien’s tricks is a variant on the eternal gruff-mentor-meets-troubled-kid drama, in which the kid learns self-confidence and the mentor learns to loosen up a little. Here the dueling duo is an Advanced English teacher in a Westchester high school and his best—or rather, his most perturbing—creative-writing student. As if conscious of the pattern, O’Brien has labored to put into it a series of sly surprises meant to jolt us into rethinking our cozy assumptions about how this familiar story will work itself out. But the jolts don’t jolt, partly because you see them being rigged well in advance—magicians who tell the audience how the trick works don’t usually get a big hand at the end—and partly because the two figures appear to inhabit entirely separate eras, as if the magic show were taking place in a time machine.
The teacher, tenured head of the English department (what American high school offers teachers tenure?), is an academic bully of the pre–World War I collegiate variety, who talks like an Irish-ized George Lyman Kittredge or Paul Elmer More, and is played by Daniel Gerroll with the pugnacious profile, trim red beard, and ringing articulateness of George Bernard Shaw. He isn’t anywhere near as open-minded as Shaw, however. His repressed, spinsterish mores, too, belong to the era before 1920, though his field of expertise is apparently modern literature, about the worst area one can imagine for someone sexually squeamish. He assigns the kids tasks like writing short stories in the styles of Joyce and Faulkner. The play takes place in 1990, when most high school English teachers would have thought that getting their students to read short stories by Joyce and Faulkner was a major achievement.
Not that the assignments faze his chosen victim, played with an appealing mix of jitteriness and cool understatement by Dan McCabe. On the contrary, having decided that the prof despises all his students, the boy has set out to undermine his enemy with a species of mental jujitsu, deliberately pushing in his stories the reality buttons that unnerve repressed souls, and making one of them a devastating analysis—which turns out to be accurate—of the teacher’s problematic psychology and its likely traumatic source. A cop’s son with some psychological troubles of his own, the budding genius also has in his backpack a secret weapon—the kind with bullets. Another of O’Brien’s games with the standard pattern is that this item gets pulled and waved about in each of the play’s four scenes but never goes off; if other aspects of the play fitted together better, he might have gotten away with this classic breach of the rules.
But the display of the gun rattles the teacher so much that his relation to the world begins to shift, causing a tense, if highly improbable, confrontation with a drunken gay colleague (a hilarious and pitch-perfect performance by T. Scott Cunningham) who has been passed over for promotion, and a woozy, fumbling erotic encounter with a young woman (rendered with delicious precision by Susan Pourfar) who turns out to be both colleague and former student, and whose view of him, elegantly caught in O’Brien’s writing, is an unstable meld of adoration and vengefulness. As with the boy, these characters hardly seem to exist in the same world as the pontificating hero, let alone the same school. It’s as if someone had given O’Brien a particularly screwy writing assignment: See what would happen if you made Mr. Murdstone a character in Blackboard Jungle.
The improbabilities come to a head in the final scene, in which student and teacher are meant to arrive at a meeting of the minds. Here, not only the clash of eras makes the situation impossible. By raising the stakes with the threat of violence, O’Brien has pushed both the relationship and the teacher’s personal disillusionment to extremes at which you can’t imagine either character being able to function. The adumbrations of school violence, teen suicide, and sexual abuse that creep into the scene seem to have wandered in from a different play altogether. Mixed with the gun, as well as the naked hostility that has preceded them in the two men’s earlier confrontation, they make the “happy” ending—the one place where O’Brien plays by the rules—seem hopelessly factitious. Still, the piece has been fluidly staged by Michael John Garcés, using Wilson Chin’s library set ingeniously to fit the various locales. The pleasure of the acting combines with the felicities inside O’Brien’s confusion to make The Dear Boy easy to take for its gleams of promise, despite its limited rewards.