In the latest American Journalism (Winter, 2010), David W. Bulla reviews his choices for the best books on the First Amendment of the U.S. Constitution. You can read his annotations for each book in the article itself which can be found in Communications & Mass Media Complete (enter from Library webpage) or in paper in the Annenberg Library.
The Idea of a Free Press: The Enlightenment and Its Unruly Legacy by David Copeland
Living the Bill of Rights: How to Be an Authentic American by Nat Hentoff
The Limits of Dissent: Clement L. Vallandigham and the Civil War by Frank L. Klement Emergence of Free Press by Leonard W. Levy
The Fate of Liberty: Abraham Lincoln and Civil Liberties by Mark E. Neely, Jr.
Freedom’s Champion: Elijah Lovejoy by Paul Simon
War and Press Freedom: The Problem of Prerogative Power by Jeffrey A. Smith
Perilous Times: Free Speech in Wartime From the Sedition Act of 1798 to the War on Terrorism by Geoffrey R. Stone
Free Speech, the People’s Darling Privilege: Struggles for Freedom of Expression in American History by Michael Kent Curtis
The Free and Open Press: The Founding of American Democratic Press Liberty, 1640-1800 by Robert W. T. Martin
Free Speech in Its Forgotten Years by David M. Rabbin
Freedom of the Press in England 1476-1776: The Rise and Decline of Government Control by Fredrick S. Siebert.