In 1973 and 1974, he was a speech writer and lawyer for Richard Nixon at The White House and then for Gerald Ford. He has been a columnist and editorial writer for The Wall Street Journal, a syndicated columnist for The Los Angeles Herald Examiner, and a frequent contributor to Barrons. He has been a regular columnist for Los Angeles Magazine, New York Magazine, E! Online, and wrote diary for ten years for The American Spectator. He also writes frequently for The Washington Post and The Wall Street Journal.

He has written and published seven novels, and nine nonfiction books. 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. His most recent book is the best selling humor self help book, How To Ruin Your Life.

He is also a 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." The show has won seven Emmies. He appears regularly on the Fox News Channel talking about finance. He is currently a celebrity judge on the CBS hit, Star Search.

Ben Stein is an honorary board member of the Tragedy Assistance Program for Survivors (TAPS), an organization that provides services to those who have lost a loved one while serving in the Armed Forces.