The 1990s saw Not About Nightingales; Stanley; Hughie; Tartuffe; Bus Stop; Holiday; Garden District; The Rose Tattoo; Uncle Vanya; The Shadow Box; Wilder, Wilder, Wilder; the musical Anna Karenina; Salome; Chinese Coffee; Search and Destroy; On Borrowed Time; Getting Married; Taking Steps; The Miser; Zoya’s Apartment; and a revival of Sweeney Todd.

The 1980s saw The Bacchae; Joanne Woodward in Candida, Eminent Domain; George C. Scott in Present Laughter; Rex Harrison and Rosemary Harris in Heartbreak House; Design for Living; Arms and the Man, starring Kevin Kline and Raúl Julia; The Marriage of Figaro, starring Christopher Reeve, Anthony Heald, Dana Ivey, and Mary Elizabeth Mastrantonio; The Caretaker; Past Tense; You Never Can Tell; Annette Bening and Tim Daly in Coastal Disturbances; Blythe Danner in A Streetcar Named Desire; An Evening with Robert Klein; The Night of the Iguana; and The Devil’s Disciple.

The 1970s included John Lithgow in Spokesong and Once in a Lifetime; Kevin Kline and Roxanne Hart in Loose Ends; Theodore Bikel in The Inspector General; Shaw’s Man and Super man, with George Grizzard, Philip Bosco, and Laurie Kennedy; Romeo and Juliet; The Importance of Being Earnest; John Wood, Mildred Dunnock, and Tammy Grimes in Tartuffe; Lynn Redgrave in Saint Joan; Vanessa Redgrave in Ibsen’s The Lady from the Sea; Pal Joey; Days in the Trees; The Night of the Iguana, starring Richard Chamberlain and Dorothy McGuire; George C. Scott in Death of a Salesman; Ah, Wilderness!, with Geraldine Fitzgerald; The Glass Menagerie, with Maureen Stapleton and Rip Torn; Jim Dale in Scapino; Irene Papas in Medea; Rita Moreno in The National Health; Anne Jackson and Eli Wallach in The Waltz of the Toreadors; James Earl Jones in The Iceman Cometh; and Raúl Juliá in a revival of Where’s Charley?.

Circle’s first production was Howard Richardson and Richard Berney’s Dark of the Moon in 1951. Tickets were sold for $1.50 apiece. City officials determined that the Sheridan Square space had been zoned as a cabaret, so tables were built around the stage, and the audience was served cookies and punch in order to meet the requirements of the cabaret laws. Other shows staged during Circle’s inaugural season included Jean Anouihl’s Antigone and Federico Garcia Lorca’s Yerma.

In 1952, Circle produced a revival of Tennessee Williams’ Summer and Smoke, starring Geraldine Page, which had failed on Broadway a few years earlier. New York Times theatre critic Brooks Atkinson attended the opening night performance, and wrote in his review that “nothing has happened for quite a long time as admirable as the new production at Circle in the Square.” Summer and Smoke became Circle’s first hit, and the Off-Broadway theatre movement took root.

Mann and Quintero had lobbied tirelessly since Circle’s inception for permission from Carlotta Monterey O’Neill to produce one of her late husband’s plays, and in 1956 permission was granted for a production of The Iceman Cometh starring Jason Robards, Jr. Circle’s burgeoning reputation was solidified by the production which, like Summer and Smoke, had originally been a Broadway failure. This success has been credited for re-establishing Eugene O’Neill as one of America’s greatest dramatists, and brought Circle numerous awards. It was followed up later that year with the American premier of Long Day’s Journey into Night, starring Frederic March, Florence Eldridge, and Jason Robards, Jr. The production garnered Tony Awards® for Best Play and Best Actor for Frederic March. Over the course of its lifespan, Circle in the Square produced nearly all of Eugene O’Neill’s major works.

The company moved to a new performance space at 159 Bleecker Street in 1960, the original home of the Amato Opera Company. The Bleecker Street Theatre’s three-sided stage allowed for democratic seating, use of a minimal amount of scenery, and for the audience to be close to the action. This style, pioneered by Circle in the Square, later became a mainstay of regional theatre. Also at this time, Quintero left the company to pursue other opportunities. Mann remained at the helm as Artistic Director, a position he would occupy until 1993. His partnership with Paul Libin, Circle’s long-time Managing Director and Producing Director, began in 1963 with their production of The Trojan Women.

Throughout the 1960s, Circle continued to develop as a home for both revivals of classic works, such as Othello and Iphigenia in Aulis, and for new and experimental works such as the American premieres of Jean Genet’s The Balcony and Brendan Behan’s The Quare Fellow. Additionally, Circle presented three critically-acclaimed seasons at Ford’s Theatre in Washington, D.C.

In the fall of 1972, Circle moved its base of operations once again, this time at the invitation of Mayor John Lindsay to the Joseph E. Levine Theatre, a 650-seat house at 50th Street and Broadway, though the Bleecker Street theatre continued to house workshops of experimental plays and productions of new works until the late 1970s. The first production in their new home was O’Neill’s Mourning Becomes Electra starring Colleen Dewhurst.

Although Circle in the Square is most often associated with Off-Broadway theatre, they had been producing shows in Broadway houses as far back as Alfred Hayes’ The Girl on the Via Flaminia in 1954. With the opening of the Uptown theatre, Circle had a permanent home on Broadway.

Circle in the Square Uptown, as it came to be known, was also the home of the Circle in the Square Theatre School, which opened in 1961 in Greenwich Village, and remains a highly regarded acting conservatory.

In its 70-year history, Circle in the Square launched or reinvigorated the careers of many playwrights, actors, and directors. Among the notable figures who worked on Circle productions are George C. Scott, Tennessee Williams, Thornton Wilder, Al Pacino, Audra McDonald, Geraldine Page, James Earl Jones, Mary Louise Parker, Vanessa Redgrave, and Norm Lewis.

It offered America’s finest actors the chance to take on demanding roles in an atmosphere free of commercial pressure, encouraging these actors to make bold choices, and responded to their desire to explore plays that fell outside the popular repertory. Circle committed to the presentation of plays not normally produced on Broadway, allowing our audiences to see challenging material unavailable to them elsewhere.