"[6] His subjects included Steven Spielberg, V. S. Naipaul, Stephen Sondheim, Oliver Stone, Muriel Spark, and Edward Gorey.

[citation needed] In 1995, Schiff was asked to write a screenplay adaptation of Vladimir Nabokov's novel Lolita, by the prospective film's then-producer, Richard Zanuck.

[11] In her New York Times review, critic Caryn James called "Stephen Schiff's discerning, faithful screenplay [...] sensitive to Nabokov's wit as well as his lyricism.

His subsequent films include The Deep End of the Ocean (1999), starring Michelle Pfeiffer;[14] True Crime (1999), directed by and starring Clint Eastwood; Wall Street: Money Never Sleeps (2010), Oliver Stone's sequel to the 1987 film Wall Street;[15] and American Assassin (2017).

[16] In 2013, Schiff became a writer and Consulting Producer of the FX television series The Americans,[17] starring Keri Russell and Matthew Rhys.

He contributed the critical essay on Nabokov's Lolita to Harvard University Press's landmark scholarly compendium A New Literary History of America, which was published in September, 2009.

[26] In December 2009, Henry Holt and Company announced that it would publish Schiff's forthcoming biography of Norman Mailer.