The following bibliography is far from exhaustive; it consists of the works that I’ve found most helpful in my own research. This list was created in November 0f 2012.
Aichele, Gary J. Oliver Wendell Holmes Jr.: Soldier, Scholar, Judge (Boston: Twayne, 1989).
Alschuler, Albert W. Law Without Values: The Life, Work, and Legacy of Justice Holmes (Chicago, Illinois: University of Chicago Press, 2001).
Baker, Liva. The Justice from Beacon Hill: The Life and Times of Oliver Wendell Holmes (New York: HarperCollins, 1991).
Bent, Silas. Justice Oliver Wendell Holmes (New York: Vanguard Press, 1932).
Biddle, Francis. Mr. Justice Holmes (New York: Scribner, 1942).
Bowen, Catherine Drinker. Yankee from Olympus: Justice Holmes and His Family (Boston: Little, Brown & Co., 1944).
Burton, David H. Taft, Holmes, and the 1920s Court: An Appraisal (Madison, New Jersey: Fairleigh Dickinson University Press, 1998).
______________. Political Ideas of Justice Holmes. Madison, New Jersey: Fairleigh Dickinson University Press, 1992).
______________. Oliver Wendell Holmes Jr. (Boston: Twayne Publishers, 1980).
Cohen, Jeremy. Congress Shall Make No Law: Oliver Wendell Holmes, the First Amendment, and Judicial Decision Making (Ames: Iowa State University Press, 1989).
Collins, Ronald K. L. and David M. Skover. On Dissent: Its Meaning in America (New York: Cambridge University Press, forthcoming 2013).
Gibian, Peter. Oliver Wendell Holmes and the Culture of Conversation (New York: Cambridge University Press, 2001). [This book focuses on Oliver Wendell Holmes Sr. but reveals much about the environment in which Holmes Jr. grew up. It also uses Harold Bloom to make sense of Emersonian communication and rhetoric.]
Hoffheimer, Michael H. Justice Holmes and the Natural Law (New York: Taylor & Francis, 1992).
Howe, Mark DeWolfe. Justice Oliver Wendell Holmes, Vol. One: The Shaping Years, 1841-1870 (Belknap Press of Harvard University, 1957).
______________. Justice Oliver Wendell Holmes, Vol. Two: The Proving Years, 1870-1882 (Belknap Press of Harvard University, 1963).
Kellogg, Frederic R. Oliver Wendell Holmes, Jr.: Legal Theory and Judicial Restraint (New York: Cambridge University Press, 2007).
Menand, Louis. The Metaphysical Club (New York: Farrar, Straus and Giroux, 2001). [This book situates Holmes alongside other classical pragmatists such as C.S. Peirce, William James, and John Dewey.]
Novick, Sheldon M. Honorable Justice: The Life of Oliver Wendell Holmes (New York: Little, Brown & Co., 1989).
Pohlman, H. L. Justice Oliver Wendell Holmes and Utilitarian Jurisprudence (Harvard University Press, 1984).
______________. Free Speech and the Living Constitution (New York: New York University Press, 1991).
Rosenberg, David. The Hidden Holmes: His Theory of Torts in History (Harvard University Press, 1995).
White, G. Edward. Justice Oliver Wendell Holmes: Law & the Inner Self (New York: Oxford University Press, 1993).
Editions of Holmes’s Writings and Letters:
Burton, David H., Editor. Progressive Masks: Letters of Oliver Wendell Holmes, Jr., and Franklin Ford (Newark: University of Delaware Press, 1982).
______________. Holmes-Sheehan Correspondence (New York: Fordham University Press, 1993).
Gordon, Robert W., Editor. The Legacy of Oliver Wendell Holmes, Jr. (Stanford University Press, 1992).
Howe, Mark Dewolfe, Editor. Holmes-Pollock Letters: The Correspondence of Mr. Justice Holmes and Sir Frederick Pollock, 1874-1932, Vol. 1 and 2 (Cambridge, Massachusetts: Belknap Press of Harvard University, 1941).
______________. Holmes-Laski Letters: The Correspondence of Mr. Justice Holmes and Harold J. Laski, 1916-1935 (Harvard University Press, 1953).
Lerner, Max, Editor. The Mind and Faith of Justice Holmes: His Speeches, Essays, Letters & Judicial Opinions (Boston: Little, Brown & Co., 1943).
Mennel, Robert M. and Christine L. Compston, Editors. Holmes & Frankfurter: Their Correspondence, 1912-1934 (Hanover, New Hampshire: University Press of New England, 1996).
Peabody, James Bishop, Editor. The Holmes-Einstein Letters: Correspondence of Mr. Justice Holmes and Lewis Einstein, 1903-1935 (New York: St. Martin’s Press, 1964).
Posner, Richard. The Essential Holmes: Selections from the Letters, Speeches, Judicial Opinions, and Other Writings (Chicago: University of Chicago Press, 1992).
Alschuler, Albert W. “The Descending Trail: Holmes’ Path of the Law One Hundred Years Later.” Florida Law Review, Vol. 49 (1997).
Bernstein, Irving. “The Conservative Mr. Justice Holmes.” New England Quarterly, Vol. 23 (1950).
Blasi, Vincent. “Reading Holmes Through the Lens of Schauer: The Abrams Dissent.” Notre Dame Law Review, Vol. 72 (1997).
Bogen, David S. “The Free Speech Metamorphosis of Mr. Justice Holmes.” Hofstra Law Review, Vol. 11 (1982).
Caplan, Gerald. “Searching for Holmes Among the Biographers.” George Washington Law Review. Vol. 70 (2002).
Cate, Irene M. Ten. “Speech, Truth, and Freedom: An Examination of John Stuart Mill’s and Justice Oliver Wendell Holmes’s Free Speech Defenses.” Yale Journal of Law and the Humanities, Vol. 22 (2010).
Feldman, Stephen M. “Free Speech, World War I, and Republican Democracy: The Internal and External Holmes.” First Amendment Law Review, Vol. 6 (2008).
Ferguson, Robert A. “Holmes and the Judicial Figure.” Chicago Law Review, Vol. 55 (1988).
Frankfurter, Felix. “The Constitutional Opinions of Justice Holmes.” Harvard Law Review. Vol. 29 (1916).
Grey, Thomas C. “Plotting the Path of the Law.” Brooklyn Law Review, Vol. 63 (1997).
Haack, Susan. “On Legal Pragmatism: Where Does ‘The Path of the Law’ Lead Us?” American Journal Jurisprudence, Vol. 50 (2005).
Leonard, Gerald. “Holmes on the Lochner Court.” Boston University Law Review, Vol. 85 (2001).
Luban, David. “Justice Holmes and the Metaphysics of Judicial Restraint.” Duke Law Journal, Vol. 44 (1994).
Mendenhall, Allen. “Holmes and Dissent.” The Journal Jurisprudence, Vol.12 (2011).
______________. “Dissent as a Site of Aesthetic Adaptation in the Work of Oliver Wendell Holmes Jr.” British Journal of American Legal Studies, Vol. 1 (2012).
Ragan, Fred D. “Justice Oliver Wendell Holmes, Jr., Zechariah Chafee, Jr., and The Clear and Present Danger Test for Free Speech: The First Year, 1919.” Journal of American History, Vol. 58 (1971).
Rosenblatt, Rand. “Holmes, Peirce, and Legal Pragmatism.” Yale Law Journal, Vol. 84 (1975).
Shea, Thomas F. “Great Dissenters: Parallel Currents In Holmes and Scalia.” Mississippi Law Journal, Vol. 67 (1997).
Snyder, Brad. “The House that Built Holmes.” Law & History Review. Vol. 30, No. 3 (2012).
Wells, Catherine Peirce. “Old-Fashioned Postmodernism and the Legal Theories of Oliver Wendell Holmes, Jr.” Brooklyn Law Review, Vol. 63 (1997).
______________ [published under the name Catherine Wells Hantzis]. “Legal Innovation Within the Wider Intellectual Tradition: The Pragmatism of Oliver Wendell Holmes, Jr.” Northwestern University Law Review, Vol. 82 (1988).