Caldwell scored first on Broadway in Tennessee Williams' Slapstick Tragedy, winning her first Tony Award in 1966 for her portrayal of Polly. Two years later she returned as a full-fledged star in The Prime of Miss Jean Brodie, winning a second Tony. In 1970 she was awarded the Order of the British Empire by HRH Queen Elizabeth II.
Since 1971, Caldwell's New York stage credits include Arthur Miller's Creation of the World and Other Business; Mary in Eugene O'Neill's Long Day's Journey Into Night opposite Jason Robards; and Lillian Hellman in the one-woman play, Lillian. In 1982, she won her third Tony Award for Medea, which was directed by her late husband Robert Whitehead. She returned to Australia to play Medea with an Australian company in 1983. Other recent credits include Terrence McNally's A Perfect Ganesh and Master Class, which won her a fourth Tony for her portrayal of Maria Callas. This past summer she performed in the Los Angeles Opera's production of Stephen Sondheim's A Little Night Music.
Caldwell's television credits include MACBETH, THE APPLE CART and THE LADY'S NOT FOR BURNING for the CBC; and THE SEAGULL for the BBC. Film highlights include Woody Allen's PURPLE ROSE OF CAIRO and the animated film LILO AND STITCH.
In 1977, she launched a directing career with An Almost Perfect Person, starring Colleen Dewhurst and George Hearn, followed by Richard II in Stratford, Ontario. Off-Broadway she directed These Men; Othello with Christopher Plummer and James Earl Jones; and Vita and Virginia with Vanessa Redgrave and Eileen Atkins. On Broadway, she directed Israel Horovitz's play Park Your Car in Harvard Yard starring Jason Robards and Judith Ivey. She has directed The Taming of the Shrew and Hamlet for the American Shakespeare Theatre in Stratford, CT
Caldwell is the 1998 recipient of the John Gielgud Award, presented by the Shakespeare Guild in conjunction with the Folger Shakespeare Library; the 1998 recipient of the Linda Wilson Lifetime Achievement Award for Excellence in the Theatre from the University of Florida; the 1999 recipient of the Bernard B. Jacobs Excellence in the Theatre Award as presented by the U.J.A./Federation of New York, and the 1999 Barnard College Medal of Distinction. She held the Eminent Scholar Chair at Florida State University, where she taught.
Caldwell is the author of the book I Will Be Cleopatra - An Actress's Journey, published by W.W. Norton Et Company.
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