While in law school, he was Editor-in-Chief of the Yale Journal of Law & the Humanities. After law school he clerked for Ronald M. Gould on the U.S. Court of Appeals for the Ninth Circuit, practiced litigation at Shea & Gardner (now Goodwin Procter) in Washington, D.C., and then served as a Climenko Fellow and Lecturer on Law at Harvard Law School.

Prof. Stern teaches and researches in the areas of law and literature, legal history, law and sexuality, and criminal law. His research focuses on the evolution of legal doctrines and methods in relation to literary and intellectual history. Current research topics include the development of the "reasonable man" standard (and its precursors and analogues) since the eighteenth century, and the changing conception of legal fictions between the early modern period and the present. His research has been funded by the Social Sciences and Humanities Research Council, the Foundation for Legal Research, and the American Society for Legal History.

He is co-editor (with Robert Spoo) of the series Law and Literature, published by Oxford University Press. With colleagues at other universities in North America, Europe, and the UK, he convenes the Works in Progress series in Law and Literature, which provides a venue for new work in the field. He is also co-editor of Critical Analysis of Law, and a co-editor of the New Rambler Review.

In 2012 Prof. Stern was the recipient of the SLS Partnership Award, bestowed by the U of T Students' Law Society in recognition of faculty members who have shown a commitment to student-friendly initiatives and student advocacy.

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