“I’m scared shitless about this show,” says playwright Jeff Whitty. On May 18 he is scheduled to unveil this season’s riskiest, most ambitious, gayest stage production not starring a web-slinging superhero: his long-awaited musical version of Armistead Maupin’s Tales of the City. With opening night looming and Tales fans champing at the bit, Whitty, who’s been working on its libretto for four years, isn’t in the mood to mince words about his anxiety. “I’m not going into this with any sort of bravado,” he says. “We’re not going to know what we have until we put it in front of people. That’s what’s exciting and terrifying about it.”

Sitting in front of a plate of eggs and toast in the back corner of a café in Manhattan’s Chelsea neighborhood, Whitty is a safe distance from the critical daggers he fears he’ll have to dodge after the show premieres at San Francisco’s American Conservatory Theater. His jitters seemingly in check, Whitty, 39, is detailing his vision for the project and holding forth on the legacy of Maupin’s popular novels as only a true Tales lover can. “I want to write for a new audience and give them a big, crunchy epic musical,” he says. “At the same time, I think of a classic like Les Miserables, which is a triumph of structure. It’s so engaging on a very primal storytelling level. If they were able to pull that off, then we can pull this off. That is my hope for Tales.”

Amused by the effusive, drama-geek grandeur of this declaration, Whitty does an about-face and clarifies: “I want to make sure it doesn’t come off like I’m saying we’re going to redefine musical theater.” He chuckles before offering a comical, catty analogy: “You know, Bono said this thing about Spider-Man where he’s like”—Whitty shifts his voice into an exaggerated, pretentious accent—“ ‘It hearkens to Walt Whitman and all these deep thinkers and ama-a-azing musicians.’ I was just like, ‘Oh, honey.’ ”

Given the precious, expansive source material, a Tales adaptation would be a daunting venture for any playwright. But if someone can translate Maupin’s complex characters and interlacing plotlines to the stage, why not Whitty? This is the writer who, in 2004, won the Tony award for Best Book of a Musical for the peppy Sesame Street–inspired puppet spectacle Avenue Q, arguably the most inventive, unexpected, and relatable Broadway production of the last decade (it also netted Tonys for Best Score and Best Musical, stunning many theatergoers when it beat out that year’s front-runner, Wicked). Conceived by composers Robert Lopez and Jeff Marx, Avenue Q, like Tales, featured disenchanted post-collegiates sharing a building, their dreams, and their angst against a hip, urban, pansexual backdrop. Also like Tales, Q tapped into the uncertainty and headiness of the 20- and 30-something generations but still managed to go down real easy thanks to its uplift and humor.

Tags: Theater