He has appeared in two films: as a mill inspector in Graveyard Shift (1990), based on the novel by Stephen King, and with his wife Margaret Perham (Grover), in Bed & Breakfast (1992), with Roger Moore and Colleen Dewhurst.
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His later directing work included a 1973 production of A Streetcar Named Desire, starring Rosemary Harris (to whom he was married from 1959–1967), James Farentino, and Patricia Conolly; a memorable production of The Royal Family in 1975 for which he won both a Tony Award and a Drama Desk Award, and a 1983 revival of You Can't Take It With You with Jason Robards and Colleen Dewhurst.
I, Don Quixote starred, in addition to Cobb, Colleen Dewhurst (in her first major role) as Aldonza/Dulcinea, Eli Wallach as Cervantes' Manservant as well as Sancho Panza, and Hurd Hatfield as Sanson Carrasco as well as a character called The Duke.
They also continued their collaboration throughout the decade as producers on TV specials, including Hedda Gabler (with Ingrid Bergman and Michael Redgrave), and The Crucible (with George C. Scott, Colleen Dewhurst, and Fritz Weaver).
Notable residents have included the 33rd Vice President of the United States Henry A. Wallace, Rolling Stones guitarist Keith Richards, the photographer O. Winston Link, the artist Charles Sheeler (American, 1883–1965), the pianist Hélène Grimaud, the composer and arranger Clare Grundman, the artist and filmmaker Ralph Bakshi, the singer and musical stage headliner Sally Ann Howes, and the actress Colleen Dewhurst.
He is living in self-imposed exile in Albufeira, a fishing village in southern Portugal, where he seeks occasional companionship from a local prostitute (Colleen Dewhurst).