Schenkkan was born in Chapel Hill, North Carolina, the son of Jean Gregory (née McKenzie) and Robert Frederic Schenkkan, a professor in the Department of Radio-Television-Film at The University of Texas at Austin, and public television executive. He grew up in Austin, Texas. As a Plan II Honors student he received a B.A. in Drama, magna cum laude, from the University of Texas, Austin in 1975 (Phi Beta Kappa, Friars' Society, UT Texas Exes Distinguished Young Alumnus Award and E. William Doty College of Fine Arts Distinguished Alumnus Award), and an M.F.A. in Theatre Arts from Cornell University in 1977. For many years, he lived in New York City and then Los Angeles, California, working both as a writer and an actor in film, television, and theatre. Since 1990 he has focused exclusively on his writing and divides his time between New York City and Seattle. Schenkkan is of Dutch-Jewish (father), and Scottish and English (mother) descent.
Schenkkan is the author of ten full-length plays. By the Waters of Babylon premiered at the Oregon Shakespeare Festival in February, 2005. The play is unrelated to the Stephen Vincent Benét short story By the Waters of Babylon or its subsequent adaptation. Lewis and Clark Reach the Euphrates premiered at the Mark Taper Forum in Los Angeles in December 2005. The Marriage of Miss Hollywood and King Neptune premiered at the University of Texas at Austin in November 2005. The Devil and Daniel Webster premiered at the Seattle Children's Theatre in February 2006.
Handler, a play dealing with a snake handling church, premiered at the Actors Express Theatre in Atlanta, Georgia. Heaven On Earth won the Julie Harris/Beverly Hills Theatre Guild Award, participated in the Eugene O'Neill Playwright's Conference, and premiered Off-Broadway at the WPA Theatre. Final Passages premiered at the Studio Arena theatre. Tachinoki premiered at the Ensemble Studio Theatre in Los Angeles and was designated a Critic's Choice by the LA Weekly. His other play for young audiences, The Dream Thief, had its premier at Milwaukee's First Stage.

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