O’Keefe’s affiliation with San Francisco’s Magic Theatre began with their 1972 premiere of his play Chamber Piece, followed the next year with his production of Jimmy Beam. Also at the Magic, All Night Long won the full round of Bay Area Critics Awards, followed by Ghosts (San Francisco Chronicle Critic’s Choice) and Bercilak’s Dream (Bay Guardian Top Ten.) All these premieres were directed by O’Keefe.
He was a regular participant in the Padua Hills Playwrights Festival where his works, Bercilak’s Dream, Don’t You Call Me Anything But Mother, Mimzabim, The Promotion and Disgrace were all first presented.
Ghosts ran in Los Angeles for five months, winning three Dramalogue Awards including best play, and an LA Weekly Award for best direction.
All Night Long was presented at the Second Stage Theater in New York in 1984 under the direction of Andre Gregory.
O'Keefe performed his one-man show, The Promotion at Lincoln Center in 1991.
His solo work Shimmer toured throughout the United States and Europe and was subsequently produced as a feature film by American Playhouse and broadcast nationally. He won the New York Bessie Award for Shimmer. Upon his return to the U.S., a production of Shimmer was staged at the Magic Theatre under a PEW Residency grant.
He returned as an artist-in-residence to the University of Iowa in 1994, with his play about the famous Brontë sisters, The Flowers of Fancy. He followed this with a film adaptation of the play that represented the United States at Sundance Institute's European affiliate, the eQuinoxe Film Institute in Bordeaux, France in 1995. O'Keefe also held residencies at Sundance Film Institute in 1989 and again in 1992.
The Deatherians, O'Keefe's musical about sex and euthanasia in Amsterdam had its world premiere at the Undermain Theater in 1996 in Dallas, sweeping their Critics Awards that year.
In the spring of 1997, The Brontë Cycle was staged at the Clarence Brown Theater, Knoxville, Tennessee where he was artist-in-residence. The Magic Theatre of San Francisco subsequently presented Brontë in 1999.
Glamour, the first play in a series featuring the character of poet Robert Graves, opened on March 15, 2001 at the Cinnabar Theater in Petaluma, CA, with O'Keefe directing. Glamour won a citation for best play by National Critics Association and was restaged at the Ohio Theatre in New York City in 2002, with Katherine Owens directing.
Times Like These, directed by O'Keefe, opened in Los Angeles at 2100 Square Feet in October of 2002, after which it moved to the Odyssey Theatre for a combined seven-and-a-half month run. It won the Los Angeles Drama Critics Circle Award for Playwriting for 2002, the LA Weekly Award for best playwriting, as well as a Top 10 production in the LA Times.
Mimzabim opened in 2000 at the Climate Theatre in San Francisco.
Spook opened on January 25, 2003, at the Cinnabar Theater and was later adapted as a screenplay.
In 2004, O’Keefe was awarded a Gerbode Foundation grant to write a libretto for the Berkeley Opera. That same year he held a NEA/TCG Residency Grant with the Odyssey Theatre of Los Angeles.
In 2006, his play Reapers was produced at the Odyssey Theater in Los Angeles.
In April 2006, he wrote the libretto for a new opera, Chrysalis, which opened at the Berkeley Opera
Also in 2006, he appeared with the Chicago Symphony Orchestra as solo performer with his own adaptation of the Finnish folk legend, Kalevala.
In 2007, he performed his solo works, The Sunshine’s A Glorious Bird as well as his adaptation of Walt Whitman’s Song of Myself at New York’s Public Theater.
He won the 2007 Bay Area Critics Award in outstanding solo performance for his adaptation of Walt Whitman’s Song of Myself, performed at the Marsh Theater.
Mystical Abyss was commissioned in 2009 by the Theatre of Yugen for an Asian Tour.
Disgrace received a production by Blank Line Collective in Chicago in September 2010.
All Night Long was restaged in Los Angeles, CA by Open Fist in September 2018.
Times Like These was presented in October 2018 by the California Stage in Sacramento, California.