Rich grew up in Washington, D.C., attending public schools.

He attended Harvard University in Cambridge, Massachusetts, where he studied American history and literature. While at Harvard, he became the editorial chairman of The Harvard Crimson, the university's daily student newspaper. He became an honorary Harvard College scholar, was a member of Phi Beta Kappa, and received a Henry Russell Shaw Traveling Fellowship. He graduated in magna cum laude with a B.A. degree in American History and Literature in 1971.

Before joining The New York Times in 1980, Rich was a film critic for Time, film critic for the New York Post, and film critic and senior editor of New Times Magazine. In the early 1970s, he was a founding editor of the Richmond (Va.) Mercury. At The New York Times, he has been the chief theater critic, senior writer for the New York Times Magazine, and as of August 2010 he is an op-ed columnist.

Rich first won attention from theatre-goers with an essay for The Harvard Crimson about the theatre musical Follies (1971), by Stephen Sondheim, during its pre-Broadway tryout run in Boston. In his study of the work, he was "the first person to predict the legendary status the show eventually would achieve", and the article "fascinated" Harold Prince, the musical's co-director, and "absolutely intrigued" Sondheim, who invited the undergraduate to lunch to discuss further his feelings about the production.

A collection of his theatre reviews was published in a book, Hot Seat: Theater Criticism for The New York Times, 1980-1993 (1998). He also wrote The Theatre Art of Boris Aronson with Lisa Aronson in 1987.

Since 2003, Rich has written regularly for The New York Times on the mass media and public relations, particularly on its coverage of U.S. national politics. His columns make regular references to a broad range of popular culture — including television, movies, theater, and literature — and draw connections to politics and current events. His column is also published in the International Herald Tribune, the international edition of the Times.

As a political commentator, Rich is often criticized by Bill O'Reilly, host of The O'Reilly Factor, a television talk show on the Fox News Channel. Rich is openly critical of Fox News, accusing it in 2004 of having a politically conservative media bias.

In a January 2006 appearance on The Oprah Winfrey Show, a weekday television talk show, commenting on the James Frey memoir scandal, Rich expanded on his usage in his column of the term truthiness to summarize a variety of ills in culture and politics.

His book The Greatest Story Ever Sold: The Decline and Fall of Truth from 9/11 to Katrina (2006) criticized the American media for its support of George W. Bush's administration's policies following the September 11, 2001, terrorist attacks.

Rich dismissed the historical-drama film The Passion of the Christ (2004), directed by Mel Gibson, as "nothing so much as a porn movie, replete with slo-mo climaxes and pounding music for the money shots", and praised Christopher Hitchens's description of it as "a homoerotic 'exercise in lurid sadomasochism' for those who 'like seeing handsome young men stripped and flayed alive over a long period of time.'"