In 1973 and 1974, he was a speech writer and lawyer for Richard Nixon at The White House and then for Gerald Ford. (He did NOT write the line, "I am not a crook.") He has been a columnist and editorial writer for The Wall Street Journal, a syndicated columnist for The Los Angeles Herald Examiner (R.I.P.) and King Features Syndicate, and a frequent contributor to Barron, where his articles about the ethics of management buyouts and issues of fraud in the Milken Drexel junk bond scheme drew major national attention. He has been a regular columnist for Los Angeles Magazine, New York Magazine, E! Online, and most of all, has written a lengthy diary for ten years for The American Spectator. He also writes frequently for The Washington Post, The Wall Street Journal, op. ed. and almost every other imaginable magazine.
He has written and published fifteen books, seven novels, largely about life in Los Angeles, and eight nonfiction books, about finance and about ethical and social issue in finance, and also about the political and social content of mass culture. He has done pioneering work in uncovering the concealed messages of TV and in explaining how TV and movies get made. His titles include A License to Steal, Michael Milken and the Conspiracy to Bilk the Nation, The View From Sunset Boulevard, Hollywood Days, Hollywood Nights, DREEMZ, Financial Passages, and Ludes. He has also been a longtime screenwriter, writing, among many other scripts (most of which were unmade ) the first draft of The Boost, a movie based on Ludes, and the outlines of the lengthy miniseries Amerika, and the acclaimed Murder in Mississippi. He was one of the creators of the well regarded comedy, Fernwood Tonight.
He is also an extremely well known actor in movies, TV, and commercials. His part of the boring teacher in Ferris Bueller's Day Off was recently ranked as one of the fifty most famous scenes in American film. Starting in July of 1997, he has been the host of the Comedy Central quiz show, Win Ben Stein's Money.
He has now finished his book for Simon & Schuster's Free Press about his life with his ten year old son named Tommy & Me. He lives with his wife, Alexandra Denman (lawyer,) his son, and every imaginable kind of pet and consumer good, in Los Angeles.