Kaplan has been a White House speechwriter; a Washington journalist; a deputy presidential campaign manager; a Disney studio executive; and a motion picture and television producer and screenwriter.

He was a program officer at the Aspen Institute; executive assistant to U.S. Commissioner of Education Ernest L. Boyer; chief speechwriter to Vice President Walter F. Mondale; deputy op-ed editor and columnist for the Washington Star; visiting scholar at the Brookings Institution; and a regular commentator on NPR's All Things Considered and on the CBS Morning News. Recruited after the 1984 election by Jeffrey Katzenberg and Michael Eisner, he worked at Disney for 12 years.

He is editor of The Harvard Lampoon Centennial Celebration (1973); co-author (with Ernest L. Boyer) of Educating for Survival (1977); and editor of The Monday Morning Imagination (1975) and What Is An Educated Person? (1980). Articles by him have appeared in publications including The New York Times, The Washington Post, The Los Angeles Times, Time, U.S. News & World Report, The American Scholar, The Woodrow Wilson Quarterly, and The New Republic.

The Norman Lear Center is a multidisciplinary research and public policy center exploring the convergence of entertainment, commerce, and society. The Center is a unique convener of entertainment industry professionals, scholars, public figures, and social critics. Through scholarship and research; through its programs of visiting fellows, conferences, public events, and publications; and in its attempts to illuminate and repair the world, the Center works to be at the forefront of discussion and praxis in the field.