Shortly before rehearsals began for her Broadway debut—a new production of Stick Fly, slated to open Dec. 8 at the Cort Theatre—Lydia R. Diamond took a one-day trip from her home in Boston to conduct a workshop in playwriting for 50 or so New York City high school teachers. The assembled educators sat on folding chairs at Manhattan High School as Diamond unlocked the secret to being a playwright.

“To demystify what I do: It’s like when you make dolls talk to one another.” She held up her hands, palm facing palm, wriggling one, then the other. “You don’t say, ‘I’m going to have Barbie say this, in order for there to be a metaphor,’ and ‘I’m going to have Ken say this, in order for there to be conflict.’ No, it just comes out.”

Indeed, Diamond began to stage homemade dramas from the age of about eight, with the dolls she bought with her allowance—Barbies, Kens, trolls (“They were Barbie’s kids,” she explains) and a G.I. Joe—despite her mother’s disapproval. Her mother objected not because all but one of the dolls Lydia bought were white—it was because, Diamond explains later, she thought Barbies were sexist. By 12, the fledgling playwright was using the dolls to act out stories she was actually writing down, including one imagining a romance between Barbie and a pitcher for the St. Louis Cardinals.

If starting a play is as simple as playing with dolls, the process of getting one produced is considerably more complex, intimidating and—many would say—political. Diamond has had more success than most. Her 10 produced full-length plays have been seen in professional theatres throughout the U.S.—so many that she is surely one of the nation’s most-produced playwrights who has not yet been seen on Broadway. Stick Fly—her play about an affluent African-American family on Martha’s Vineyard—has already received close to a dozen full productions across the country, as well as numerous readings and workshops.

Now Stick Fly is set to open on West 48th Street with a six-member cast including Dulé Hill, Tracie Thoms and Ruben Santiago-Hudson. The show is directed by Kenny Leon and produced by recording artist Alicia Keys, who will also compose the play’s incidental music.

Diamond expresses ambivalence about landing on Broadway at age 42 with a play that has been bouncing around the country since its 2006 premiere at Chicago’s Congo Square Theatre. “I feel humbled and a little messed up,” she confesses on the ride to the airport for her flight back to Boston, where she teaches playwriting at Boston University. “The exposure, the buzz, is genuinely exciting,” she allows. “But it sits in a place that’s a little bit uncomfortable.”

What’s most evidently uncomfortable for Diamond is accounting for her success. “My whole personal charm has been predicated on being self-effacing,” she likes to say, half-confiding, half-joking.

Since she had just spent several hours instructing teachers how to answer questions about characters they made up on the spot, I asked Diamond to view herself as a character: If she were not Lydia Diamond, how would she explain Lydia Diamond’s theatrical track record?

She accepted the assignment. “If I didn’t know her, I’d think: ‘Who does she know, and what is she doing that I’m not doing?’ If I liked her, I’d say: ‘She writes plays that people want to put on. She likes actors, she respects directors, she’s pretty good at listening, she doesn’t have enemies.’”

But she returned quickly to being the real Lydia Diamond: “I have been privileged to get my work recycled; I can see clearly how arbitrary and inequitable the system is. I have too many friends who are brilliant artists and wonderful people, who don’t get the opportunity of multiple productions—or being on Broadway.”

So why has she succeeded?

Ask Peter DuBois, artistic director of Huntington Theatre Company of Boston, which produced Stick Fly in 2010 and sponsored readings of three of her other plays. “She’s a really great writer,” DuBois says. Huntington also made her a playwright fellow for two years and is, according to DuBois, “committed to providing her with an artistic home.”

“She knows how to entertain, how to grab the heart; she has a great sense of humor and a lot to say,” elaborates Emily Mann, artistic director of McCarter Theatre Center in Princeton, N.J., which produced Stick Fly in 2007 and has mounted staged readings and workshops of Diamond’s other plays. McCarter also provided her with two artist retreats, commissioned a play from her and, “has built a strong bond with Lydia.”

Her plays are “fearless,” ventures Russ Tutterow, artistic director of Chicago Dramatists, the very first theatre to give Stick Fly a reading, back in 2003.

“She assumes her audience is as smart as she is; she never takes them for granted,” posits Kenny Leon, who has been involved in the play since its production in 2007 at True Colors Theatre Company in Atlanta, where he is the artistic director. “She should have gone to Broadway before now,” Leon adds. “People who have had her success usually do.”

Leon is directing two plays on Broadway this season. The other is The Mountaintop by Katori Hall, another female African-American playwright making her Main Stem debut. Also this season, Porgy and Bess will bow with a new book by Suzan-Lori Parks, and veteran Broadway producer Elizabeth I. McCann has announced her intention to bring to Broadway By the Way, Meet Vera Stark by Lynn Nottage. That would mean four black female playwrights in a single season on the Great White Way. (In the entire history of Broadway to date, only six other black female playwrights have ever been produced: In addition to Parks, there were Lorraine Hansberry, Ntozake Shange, Regina Taylor, Sarah Jones and Vinnette Carroll.) “It’s huge and weird,” Diamond says, “that it’s happening all at once.”

Diamond began seeing Broadway shows at around age eight—touring productions presented in the University of Massachusetts Fine Arts Center that her mother managed. “I grew up with no money, lots and lots of books and a single mother with a Ph.D.” The first “grown-up play” she saw at her mother’s theatre was The Elephant Man. “The audience was disturbed that I was there, because I was so young.”

As a child, Diamond (née Gartin) studied violin and piano, met famous artists through her mother, and never lived anywhere longer than a few years, as her mother pursued an academic career in Detroit, where Diamond was born, as well as in Carbondale, Ill.; Itta Bena, Miss.; Amherst, Mass.; and Waco, Tex. The only geographical constant came during summers, which she spent with her grandparents, both educators, in the little town of Sparta, Ill.

Her high school in Waco had “a pretty decent theatre program,” and among the parts she played was Vera in Agatha Christie’s Ten Little Indians. Although the character is involved in a romance, she recalls, “They wouldn’t let us kiss at the end because I was black. I was the only black kid doing theatre.”

She graduated to being virtually the only black college kid doing theatre at Northwestern. Her aim was to be an actor—she spent 10 years identifying herself as one, while waiting tables, teaching and writing: “I was writing plays long before I thought of myself as a playwright.” She wrote her first adult, non-Barbie play for an undergraduate course, and decided in 1992 to put it on herself in the basement of a vegetarian restaurant in Chicago called Café Voltaire, where she also worked as a cook. She created her own theatre company to do so, and called it Another Small Black Theatre Company With Good Things to Say and a Lot of Nerve Productions. 

A sociologist named John Diamond saw one of her early plays and was, in his words, “blown away. She grappled with the issues of race, class, sexuality and marginality that are infused in all of her work but, because it was essentially a one-woman show and somewhat autobiographical, it was very personal. I felt like I knew her a lot better.” 

John Diamond would become her spouse as well as an occasional dramatic source: “In The Gift Horse, one of her characters says, ‘I’m a pretty spiritual person…I commune with the trees when I’m jogging.’ I heard the line and knew (embarrassingly) that I had said something similar in the past.”

Diamond the playwright credits “the culture of Chicago theatre” for her work eventually being produced by a range of theatres in the city, including Steppenwolf Theatre Company and Goodman Theatre. Eventually her husband got a job teaching at Harvard Graduate School of Education, and after many years in Chicago, she moved to Boston six years ago.

Diamond’s subjects have varied, but her work generally alternates between black history plays and contemporary dramas with autobiographical elements that use humor to sweeten a sometimes dark exploration of family relationships, race, gender and class. Among her early successes were theatrical adaptations of the poems of Nikki Giovanni, Here I Am…See Can You Handle It, and Toni Morrison’s novel, The Bluest Eye.

Diamond’s frustration with her opportunities as an African-American artist led her to write Stage Black, about a black playwright who tries to write the “perfect producible black play,” in the words of Dramatic Publishing, until her characters rebel. Reviewing a recent production, Chicago Tribune critic Kerry Reid said the play “delivers plenty of beefy laughs at the expense of both the self-appointed guardians of black cultural heritage and well-meaning white liberal audiences who expect tales of sexual abuse, self-sacrificing women, angry young men and wise-if-randy grandfathers in plays about black family life.”

It was while writing an emotionally draining black-history play that Diamond decided to take a break and “experiment with a light, well-made play.” The result was Stick Fly, which takes place in the black enclave within Martha’s Vineyard. The father in the play is a neurosurgeon who “married up.” His overeducated wife is a member of the black aristocracy, an aristocracy that could not accept him because he couldn’t pass the “paper bag test”—i.e., his skin was not lighter than a brown paper bag. Their two sons, a plastic surgeon and a first-time novelist, bring home dates, one of them white, the other a young black woman named Taylor, an entomologist (who studies, among other bugs, flies). Taylor is the resentful daughter of a famous father she never knew and a “single mother college professor.”

“All the characters are pieces of me,” Diamond says, although she acknowledges that Taylor comes the closest. From the first few moments of the play, there is surprise upon surprise. Even the maid has secrets.

“Artistically, Stick Fly was ready to go to Broadway after our production in 2007,” says the McCarter’s Mann. “We could not get producers down here to look at it.”

Four years and several productions later, with reportedly few changes to the script, the show is making its move. “I think the magic word,” says McCann, “is Kenny Leon.” The director offers a businesslike accounting of why he was able to make it happen. “I thought it had great roles for six incredible actors. It wasn’t too small. I thought the subject matter would be of interest to traditional Broadway audiences, and that would combine with the black upper-class who could afford the tickets. It would also appeal to the intellectual crowd. The play takes place on the Cape; all the folks in Boston would come. And then there are all the people who have seen it in regional theatres.”

To Chuck Smith, a resident director at the Goodman, who directed Stick Fly’s Congo Square premiere, this last demographic is the most crucial. “The play has proven its popularity nationwide,” says Smith. “If by chance it is not received well on Broadway, I predict that the play will still be granted a long life—in educational, community, local professional and regional theatres.”

Can Diamond demystify the process of getting produced at any of these levels the way she has her playwriting process? Frankly, no. “There is no formula to getting produced,” she reasons. “I worry for playwrights defining their worth by the whims of producing organizations. You write the plays you write, you do your best to get it right, and the rest happens.” And if it doesn’t? “I’m a huge fan of self-production.”

Cue the Barbies.

Jonathan Mandell is a critic and journalist based in New York City. He is on Twitter as @NewYorkTheater.