After completing The Drama League's director's training program in 1987, Christopher Ashley served as assistant to Evan Yionoulis on Richard Greenberg's one-act "The Author's Voice" which was presented as part of Marathon '87 at the Ensemble Theatre Studio. He graduated to full-fledged stager with the 1989 Off-Broadway play "The Night Hank Williams Died" and then garnered notice directing Anna Deavere Smith in her one-person, multi-character drama "Fires in the Mirror: Crown Heights, Brooklyn and Other Identities" at the New York Shakespeare Festival's Public Theater. Ashley hit his stride in 1993 teaming with comic writer Paul Rudnick on "Jeffrey", a timely examination of homosexual love in the era of AIDS which proved to be an Off-Broadway hit, and staging Claudia Shear's acclaimed autobiographical one-woman show "Blown Sideways Through Life". (Two years later, he would segue to other media recreating his efforts with the feature version of the former and the PBS television adaptation of the latter.)
Now an established presence in New York theater, Ashley remained busy throughout the remainder of the decade, reteaming with Rudnick to stage the playwright's comedies "The Naked Truth" in 1994, a Chicago production of "I Hate Hamlet" in 1995 and the 1999 Off-Broadway comedy "The Most Fabulous Story Ever Told". The director quickly became known for his fluid stagings and his extraordinary capabilities with actors. He enjoyed a success with "Bunny Bunny", playwright Alan Zweibel's memoir of his friendship with the late comedienne Gilda Radner in 1996 and branched out into musicals with "Lucky in the Rain" at the Goodspeed Opera House in 1997, the Encores! concert version of "Li'l Abner" in 1998 and the Drama Dept.'s revival of the Irving Berlin revue "As Thousands Cheer" (also 1998). Following an acclaimed production of Alan Ayckbourn's comedy-drama "Communicating Doors" (1998, with a stellar leading turn by Mary-Louise Parker), Ashley made his Broadway debut with the less successful thriller "Voices in the Dark" in 1999. A throwback to the melodramas of the 1950s (along the lines of "Sorry, Wrong Number" and "Dial M for Murder", John Pielmeier's play failed to impress critics or audiences and was a rare misstep for the director. He bounced back with the Drama Dept.'s production of Douglas Carter Beane's comedy "The Country Club", which earned good notices. In 2000, Ashley returned to the Great White Way at the helm of the revival of the camp classic "The Rocky Horror Show", which featured an eclectic cast ranging from Dick Cavett and Joan Jett to Broadway veterans Tom Hewitt and Daphne Rubin-Vega.