[3] 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.

Handler, a play dealing with a snake handling church, premiered at the Actors Express Theatre in Atlanta, Georgia.

Tachinoki premiered at the Ensemble Studio Theatre in Los Angeles and was designated a Critic's Choice by the LA Weekly.

The Kentucky Cycle underwent several years of development, starting in New York City at New Dramatists and the Ensemble Studio Theatre.

The two part epic was later workshopped at the Mark Taper Forum, EST-LA, the Long Wharf Theatre, and the Sundance Institute.

The complete "cycle" was awarded the largest grant ever given by the Fund for New American Plays and had its world premiere in 1991 at the Intiman Theatre in Seattle (Liz Huddle, producer) where it set box office records.

In 1993 it appeared at the John F. Kennedy Center in Washington, D.C., and opened on Broadway in November of that year where it was nominated for a Tony, Drama Desk, and Outer Critics Circle awards.

His play All the Way, about the behind-the-scenes political maneuvering of President Lyndon Baines Johnson to pass the Civil Rights Act of 1964, premiered at the Oregon Shakespeare Festival on July 28, 2012.

It opened in Boston at the American Repertory Theater on September 19, 2013, starring Bryan Cranston and sold out its entire run.

Schenkkan's film work includes: The Quiet American, directed by Phillip Noyce and starring Michael Caine (who received an Oscar nomination).

He appeared as Lieutenant Commander Dexter Remmick in the Star Trek: The Next Generation episodes "Coming of Age" and "Conspiracy".