From a prominent, success-oriented New York family, Wasserstein attended Mount Holyoke College and she utilized those years as the basis for her breakthrough play "Uncommon Women and Others", first produced at Yale Rep in 1975 and later in New York before a 1978 PBS adaptation that boasted a cast including Meryl Streep, Swoosie Kurtz, and Jill Eikenberry aired. The play focuses on several students of a woman's college just as the feminist revolution and other social changes were beginning. The characters are the last members of a residence house subjected to the white glove rules of etiquette, floundering, unsure of where they stand, perhaps too conservative in their upbringing to be part of the new age, yet also liberal enough not to be affected by the upheavals of the day. Wasserstein is said to be seen autobiographically as the overweight Jewish character, quick with a quip, but poignantly searching for a male connection in a phone conversation with a male student she barely knows from a nearby college. (This character could also said to be a proto-Heidi.) "Uncommon Women" seemed a breakthrough for its age that 20 years after its PBS run the network aired a reunion special including a roundtable discussion with Wasserstein and the cast (sans the busy Streep), which demonstrated how the play had heralded a new consciousness for women.

Wasserstein earned her MFA at the Yale School of Drama and her first NYC production was "Any Woman Can't" (1973), produced at Playwright's Horizons, where she would have numerous plays workshopped and premiered. She scored an Off-Broadway success with the long-running comedy "Isn't It Romantic?" (1983) but was still virtually unknown outside the New York theater world when "The Heidi Chronicles" became a hit. Her follow-up, "The Sisters Rosensweig" (1992-93), about three siblings that was as much autobiographical as it was inspired by Chekhov was a success and featured fine lead performances from Jane Alexander, Madeleine Kahn and Frances McDormand. It dealt with a host of issues ranging from anti-Semitism to sexism yet managed to be entertaining. She faltered somewhat with "An American Daughter" (1997), inspired by recent political events wherein a minor indiscretion in someone's past is blown out of proportion by the media. So beloved is Wasserstein by her actors, particularly the female ones because of the depth of her women characters, that at the 1997 Tony Awards ceremony Lynne Thigpen, winning for her work in "An American Daughter", accepted her Tony by thrice repeating "Wendy Wasserstein, Wendy Wasserstein, Wendy Wasserstein" and saying it would be "my new mantra".

Prior to the mid-90s, Wasserstein had worked little in TV and film, writing one of the three acts of "Liza Minnelli in Sam Found Out: A Triple Play" (ABC, 1988), in which Minnelli is a dance instructor coping with the affections of a klutzy student. Wasserstein had numerous screenplays in various stages of development in the 90s, but the first to reach production was her adaptation of "The Object of My Affection" (1998), co-written with director Nicholas Hytner. Adapted from Stephen McCauley's novel, the film focuses on an unwed mother and her relationship with her gay roommate.

Wasserstein has achieved her own celebrity status, in part because she one of the few commercially successful playwrights of her generation. She has acted on stage in "The Hotel Play" (1981) at La Mama Experimental Theatre and appeared in as a stage mother in James Lapine's "Life With Mikey" (1993). In addition, Wasserstein is a frequent and welcome guest on Charlie Rose's PBS talk show.