Wendy Wasserstein, who won a Pulitzer Prize, a Tony Award and considerable popularity writing comic yet pointed plays and essays about the nagging choices and disappointments that Baby Boom women encountered on the path to “having it all,” died Monday. She was 55.

Wasserstein, who had been battling cancer in recent months, died at Memorial Sloan Kettering Cancer Center.

“Today is unbearable,” Andre Bishop, artistic director of the Lincoln Center Theater, said after announcing her death. “She was very much like the women she wrote the plays about. She connected to people in her plays in a personal way. I think that’s what made her distinctive and I think a lot of people – men and women – felt as if they knew her through her work. There are artists and performers like that you kind of feel you know them even when you don’t. She was a great, great person.”

Wasserstein secured her place in American theater with four consecutive plays, from “Uncommon Women and Others” (1977) to “The Sisters Rosensweig” (1993) that traced women’s progress from college to middle age in the wake of the feminist revolution of the 1960s. Part of their strength and charm, Wasserstein’s admirers said, was that they weren’t sociological sketches of a generation, but highly personal stories anchored in her own experiences with family and friends.

The third in her informal series, “The Heidi Chronicles,” won the Pulitzer Prize for drama and the Tony Award for best play in 1989 – but it raised some prominent feminist eyebrows, including Betty Friedan’s, for an ending in which a committed feminist art historian, feeling sad, isolated and let down by the movement’s lost promise of enduring comradeship and solidarity, decides to adopt a baby.

“I’m just not happy. I’m afraid I haven’t been happy for some time,” protagonist Heidi Holland says near the end of a long, rambling, extemporaneous speech to her high school alumnae association, supposedly on the achievements and prospects of the women’s movement, of which she is considered a distinguished exemplar. “I don’t blame any of us. We’re all concerned, intelligent, good women. It’s just that I feel stranded. And I thought the whole point was that we wouldn’t feel stranded. I thought the point was that we were all in this together.”

Wasserstein said she wasn’t trying to discredit feminism, which she regarded as a life-changing inspiration, but to write what seemed most truthful for her character. But she wanted to open eyes to the trap of trying to “have it all.”

Wasserstein’s career took off in 1977 with “Uncommon Women and Others,” begun while she was earning a master’s degree at the Yale School of Drama in 1976. It assessed the glowing yet uncertain hopes of a group of friends during and after college at Mount Holyoke, the elite women’s school where Wasserstein, the youngest of four children in a wealthy, high-achieving New York family, earned her B.A. in 1971.

“When we’re 25, we’re going to be pretty (expletive) incredible,” says Rita, one of the play’s brainy and attractive collegiate characters. “All right, I’ll give us an extra five years for emotional and career development. When we’re 30, we’re going to be pretty (expletive) amazing.” By play’s end, six years after graduation, the former dorm-mates have gotten an inkling that the path to fulfilling careers and relationships might not be quite so easy, and the timetable for an incredible life has been pushed back to 40 or 45.

The show was noteworthy for its cast of future stars who were then unknown: Glenn Close, Jill Eikenberry and Swoosie Kurtz (Meryl Streep, Wasserstein’s friend from Yale, took over for Close when the play was redone for a PBS broadcast in 1978).

Besides being an industrious writer, Wasserstein was an avid traveler and socializer and a woman whose need to nurture led her on an eight-year journey through fertility treatments culminating in motherhood at 48. She was known for self-deprecating humor, sharp wit and an enthusiastic, outgoing nature that came across in her numerous lectures and TV talk show appearances, in addition to her plays and her frequent essays for newspapers and magazines, which are collected in the books “Bachelor Girls” and “Shiksa Goddess (Or, How I Spent My Forties).”

Her “combination of sweetness and wit is true, and people embrace her for that,” theater critic Robert Brustein, who got to know Wasserstein as dean of Yale’s drama school, said in a 1997 New Yorker profile of the playwright. “Being with Wendy, you feel like you’re having a bubble bath, or an ice cream soda.”

Those qualities attracted a glittering roster of friends from the worlds of theater and media. At Yale, she made lasting connections with Meryl Streep, Sigourney Weaver and playwright Christopher Durang. Charlie Rose repeatedly had Wasserstein as a guest on his late-night PBS show. She dedicated her most overtly political play, “An American Daughter,” (1997) to writer Michael Kinsley, and another friend, Frank Rich, now a political and cultural columnist for The New York Times, recused himself from reviewing her plays when he was the paper’s theater critic.

She was born in Brooklyn to two Polish-Jewish immigrants, Morris and Lola Wasserstein – the father an inventor and manufacturer of gift wrapping and decorative items, the mother a larger-than-life personality who relished daily dance lessons. Going to Saturday matinees on Broadway was a weekly childhood ritual, Wasserstein recalled in a 1997 article for the New York Times in which she detailed a pro gram she created to interest New York children in theater.

Her brother, Bruce Wasserstein, is a well-known Wall Street investment banker; he also owns New York Magazine and other periodicals. The eldest sister, Sandra Meyer, became a high-ranking bank executive before her death from breast cancer in 1997, at 60. Another sister, Georgette Levis, operates a Vermont inn with her psychiatrist husband. She also is survived by her daughter Lucy Jane Wasserstein and her mother Lola Wasserstein, both of New York City.

Wasserstein told the New Yorker that as “the youngest in a family of very large personalities,” humor became her niche – and her defense mechanism. “I’ve always been funny,” she said.

“Isn’t It Romantic,” an off-Broadway hit in 1983, grew out of her parents’ pushy desire to see her married to a good, solid, Jewish doctor or lawyer. Instead, Wasserstein remained single all her life, writing comic essays about her romantic setbacks and jokingly referring to a series of close, long term male friends as her “husbands.”

“The Sisters Rosensweig” was modeled on Chekhov’s “The Three Sisters” and on the three Wasserstein sisters. It raised issues of Jewish identity while questioning whether romance can still light up lives that have moved well into middle age. She said the impetus for the 1992 play, which ran 16 months on Broadway, was “to write smart and funny parts for women over 40” because she knew “too many actresses whose career opportunities had diminished because they made the grievous error of growing older.”

While Wasserstein earned many glowing reviews, some critics questioned whether she achieved depth along with the laughter and popularity that often come with good comic writing.

Her first novel, “Elements of Style,” is scheduled to be published by Knopf in May.

In her third book of humor, “Sloth,” a parody of self-help literature, the author shows how to shed the stress of ambition and find the ease that comes with not caring

“Today is such a sad day because I think Wendy had a lot more to say,” said Susan Dietz, who produced Wasserstein’s plays “Uncommon Women and Others” and “Isn’t It Romantic” in Los Angeles. “She was an extraordinary playwright, but also an amazing woman, so intelligent and funny and giving and generous, and I’m just really sad today and sad for her daughter. Fifty-five is too young.”