In 1970, he wrote the play titled, ‘Lakeboat’, which was a semi-autobiographical play. A revised version of the play was produced on stage almost a decade later.
In 1972, he came out with the play titled, ‘The Duck Variations’, which is the story of two elderly men involved in discussions in a park, where they watch ducks.
In 1974, his play, ‘Sexual Perversity in Chicago’ was first premiered at the Organic Theatre Company, Chicago. The following year, it was made into an off-Broadway play and was showcased at St. Clements Theatre in New York.
In 1974, he directed his one-act play, ‘Squirrels’, whose first production was staged at St. Nicholas Theater Company in Chicago, Illinois. The play was a comedy.
In 1975, his play, ‘American Buffalo’ premiered at the Goodman Theatre in Chicago. In 1977, the play opened on Broadway and received immense positive reviews.
In 1976, his play about the suppression of alternative energy technologies, titled, ‘The Water Engine’ was staged for the first time at the The Public Theater by Steven Schachter.
In February, 1977, his play, ‘A Life in the Theatre’, was first staged at the Goodman Theatre, Chicago, Illinois.
In 1981, he wrote the screenplay for the film, ‘The Postman Always Rings Twice’, which was directed by Bob Rafelson. The film however, did not receive any positive reviews.
In 1982, he wrote the screen play for the Academy Award nominated film, ‘The Verdict’. He earned an Academy Award nomination in the “Best Screenplay” category.
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On September 21, 1983, his play, ‘Glengarry Glen Ross’ premiered at London’s Royal National Theatre. The play also opened on Broadway the following year.
In 1985, his four act play, ‘The Shawl’ premiered in Chicago at the Goodman New Theatre Company. The plot of the play is centred on two men who intend to deceive a woman and gain her inherited property.
In 1987, he made his directorial debut with the film, ‘House of Games’, for which he also wrote the screenplay. The film received good reviews and was praised by film critics.
In 1991, he wrote and directed the crime-drama film, ‘Homicide’, which was showcased at the Cannes Film Festival the same year. The film was critically acclaimed.
In 1997, he co-wrote the screenplay for the Academy Award nominated film, ‘Wag the Dog’. The film earned him an Academy Award nomination for the Best Adapted Screenplay category.
He wrote the screenplay for the 1998 crime thriller film, ‘Ronin’, which was directed by John Frankenheimer. The film was well appreciated and positively reviewed by critics.
In 1999, his play, ‘Boston Marriage’ premiered at the American Repertory Theater in Cambridge, Massachusetts. That year he also directed the period drama film, ‘The Winslow Boy’.
In 2004, he wrote and directed the political thriller film, ‘Spartan’, which received mixed reviews. Some film critics also claimed the film to be a let-down.
In 2006, he published the book, ‘The Wicked Son: Anti-Semitism, Jewish self-hatred, and the Jews’. The book was a collection of different essays on the topic of Jewish identity.
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In December 2009, his play ‘Race’ premiered on Broadway at the Ethel Barrymore Theatre, New York. The play also opened across the United States in regional theatres.
In 2012, his play, ‘The Anarchist’ made its debut on the Broadway in New York. The play starred Patti LuPone and Debra Winger, who made her Broadway debut with this play.