The Apollo Theater has a rich theatrical history. For its inaugural engagement, producers Oken and Brett chose Albert Innaurato's Gemini, which featured the production's original Broadway director, Peter Schifter. David Mamet's Sexual Perversity in Chicago became a smash hit at the Apollo, starring Jim Belushi in his dramatic stage debut and directed by former Second City artistic director Sheldon Patinkin.

Long-running productions include Harry Chapin: Lies and Legends, Steel Magnolias, and Pump Boys and Dinettes, which set a Chicago longevity record for a musical by running five years.

The Apollo Theater has also played home to many productions by the acclaimed Steppenwolf Theatre Company, including Balm in Gilead with John Malkovich and Gary Sinise, Cloud Nine, Secret Rapture, Harvey, Wrong Turn at Lungfish, and Sam Shepard's True West.