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"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 cafe 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.

Whitty first discovered Tales of the City in 1993, three years after the Coos Bay, Ore., native came out to his family. He'd just graduated from the University of Oregon and decamped to New York City, where at 22 he moved into a tiny studio apartment on the Lower East Side. He hadn't yet begun his studies in New York University's graduate acting program and was waiting tables at the popular theater district restaurant Joe Allen. Alone but starry-eyed, he found solace in Maupin's novels. "Those characters became my temporary friends because I didn't know anyone here," Whitty recalls. "I wasn't in school yet. I didn't have any way of meeting people, so Mary Ann and Mouse and all those folks became my buddies when I tore through those six books."

He devoured the collection in a month, but when the first novel was made into a television miniseries -- produced by Channel 4 in the U.K. that same year, then picked up by PBS in the U.S. in 1994 -- he refused to watch it, not wanting to taint his own mental picture of 28 Barbary Lane. Showtime eventually coproduced and aired More Tales of the City in 1998 and Further Tales of the City in 2001, but Whitty continued to ignore the persistent efforts of his longtime partner, writer Steven Schmersal, to get him to watch the show, which included career-defining performances by Laura Linney, in her breakout role as Mary Ann, and Olympia Dukakis, who played pot-growing trans matriarch Anna Madrigal.

It wasn't until April 2006 that Whitty's Tales remake began to take shape. After completing Avenue Q, his first musical libretto, he was reluctant to jump back into writing, underwhelmed by the new offers coming in. "Avenue Q was truly a draining, exhausting experience," he says. "I took a ton of meetings and said no to everything because there was nothing that felt worth the struggle to write a musical." Then one day, on a plane ride to London to cast the West End production of Avenue Q, he popped in a DVD of the first Tales installment. "It's Mary Ann on the phone to her mother saying, 'I'm not coming back to Cleveland. I am embarking on this exciting new journey,' " he says, remembering the opening scene, in which the naive heroine arrives in San Francisco's Russian Hill. "I thought, That's how a musical starts -- you plunge someone into this new world. They're bringing their old way of living into this new environment."

Upon landing, Whitty checked on the rights to the story (Maupin has collaborated on several smaller Tales-themed musical projects) and found they were available. By July he was on a flight to San Francisco to pitch his idea to Maupin. "I was super nervous to meet him for the first time," Whitty says. "But when I got to Armistead's he said, 'Do you get high?' We got baked and laughed for a few hours, and I don't think I got all the way through my presentation. How could I say no? It was like being asked by Mrs. Madrigal herself!" After that, his Tales musical was a go. Though Maupin has made a few suggestions, contributing some of the show's song titles, the novelist has taken a mostly hands-off approach to the production.

The stage version of Tales reunites Whitty with gay Avenue Q director Jason Moore and features a score by Scissor Sisters front man Jake Shears and the band's touring keyboardist, John "JJ" Garden. Divided into two acts and clocking in at two hours and 45 minutes, it primarily mines the first Tales novel, originally published in 1978, while also touching on a few choice moments from its 1980 sequel, including the memorable scene in which Michael "Mouse" Tolliver, now played by actor Wesley Taylor (The Addams Family, Rock of Ages), comes out to his mother in a letter. For Whitty, telescoping Maupin's work was a difficult but necessary decision. "Most musicals have the A story and the B story. This has the F story and the G story," he says. "But we've done a ton of slenderizing because people don't want to sit through a 17-hour musical."

Though Tales follows a recent spate of gay-themed adaptations and revivals -- Priscilla Queen of the Desert, La Cage aux Folles, Angels in America -- Whitty insists he isn't simply waxing nostalgic or cashing in on a trend. For him, the themes and underlying message of Tales couldn't be more relevant today. "From a gay perspective, it's shocking how little has changed," Whitty says. "Act 2 of Tales of the City opens with Anita Bryant giving a speech to the audience, and the things she says are the same arguments that Maggie Gallagher is pulling out now. And I think there's something universal about characters who want to find family, manifest who they are, and be open and free. That's the struggle of most of the characters in this show."

Shears, who discovered Tales while in his early teens, agrees: "It's timeless, like a Greek myth or something. The characters are so ingrained in your psyche; they're so strong." Since jumping on board when Whitty told him about the project four years ago, the musician has composed more than 20 tracks for the production. (Whitty describes the songs as "the 1940s via the 1970s via now.") Shears exhibits a particular fondness for Anna Madrigal, one of the first positive portrayals of a trans character created for a mainstream audience. He's so enamored of the character that he wrote "Next Time You See Me," a revelatory, roof-shaking ballad for Madrigal (played by Judy Kaye) to close the first act.

While Tales revolves around the self-discovery of Michael and San Fran newcomer Mary Ann (played by Betsy Wolfe in the musical), Whitty also has a soft spot for Mrs. Madrigal -- and these days, for trans characters in general. "I think transgender people haven't had their turn yet in the public eye in the way they deserve," he says. "I guess part of me is just so bored with gay people. I'm all about transgender people." The playwright's recent musical Bring It On, based loosely on the 2000 cheerleader film and set to start its national tour in the fall, also features a trans character, a fierce queen bee of an inner-city high school named La Cienega. She seems different from her peers, but she never explicitly addresses her gender. "I saw her most often as the 'straight woman,' the voice of reason amid the more eccentric characters around her," Whitty says. "I didn't want to go in the 'sassy black' direction because it's been done, done, done."

When Bring It On premiered in Atlanta in January, Whitty says the performance was met with glowing reviews: "Her curtain call always got one of the biggest ovations. The audience completely loved her throughout the show and appreciated that we weren't sermonizing about it. For once we weren't getting a sob story. There was something utopian about it."

This time, Whitty doesn't backpedal or try to tone down the grand idealism of his statement. "That's the world I live in," he adds. "You're not always explaining who you are. You just are."
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