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Clifford Glimmer, alter ego of playwright Warren Leight, sums up his family’s sad history when he says, “From what I understand, everyone was happy before I was born.” In Side Man, Clifford (Chris Stezin) addresses the audience directly and plays himself as he tells the story of his parents—his trumpet-playing “side man” father and depressed, alcoholic mother—who meet in a New York hotel in the ’50s. Smiling “Clean Gene” Glimmer (Kevin Adams) seems an unlikely match for unbelievably naive (yet somehow sewer-mouthed) Terry (Amy McWilliams), but they bond over the late-night, intoxicating culture of jazz. Their resulting son grows up in this too-adult society: “Your kid has great rope,” Gene’s trombonist friend Jonesy remarks, and 20-year-old Clifford wonders, “What do you say when an ex-junkie compliments your veins?” Leight’s humor provides a bittersweet glaze to the deterioration of his parents’ lives. Terry can’t suppress her rage and disappointment at Gene when the family sits down to dinner: Her version of “Bon appétit” is “Enjoy your macaroni, motherfuckers!” Despite Clifford’s belief that his birth meant the end of happiness, he holds his parents together, to the verge of sacrificing his own life to be caretaker to them both. (Leight based Gene Glimmer on his own father, jazz trumpeter Donald Leight, who played with such band leaders as Woody Herman and Buddy Rich.) Despite a prodigious talent, Gene is undone by his refusal to adapt to changes in the music business; Leight brings him to full engagement with life only when he and some bandmates discover a bootleg tape of his son’s namesake, trumpeter Clifford Brown, recorded the night Brown died. Keegan Theatre director Leslie A. Kobylinski lets this moment play out at length, encapsulating the tragedy of a man whose love for music precludes his ability to truly love anything else. McWilliams creates an arc for the doomed Terry from a brittle but wide-eyed camp follower to an embittered, suicidal mother whose 10-year-old son literally has to pull her off the ledge. But both the structure and the emotional weight of the show are on Stezin’s able shoulders, and he is in turns poignant and rueful. Leight calls on him to step into the action and play himself at all ages, and when child Clifford must assume adult responsibilities, some of the impact is lost when he’s played by an adult. Still, the desolation Gene’s life wreaks on his family is palpable. As Clifford marvels at his father’s performance at the run-down Melody Lounge, he asks their old friend, jazz groupie Patsy (Charlotte Akin), “Do you think he’ll make it?” “Honey,” she says, “this is it.”—Janet Hopf