Michelle Pfeiffer has reflected on her brief stage career, revealing that a 1989 production of Shakespeare's Twelfth Night remains the most terrifying role of her career, one she would never repeat. The show, staged at the Delacorte Theatre in Central Park as part of the New York Shakespeare Festival, was intended to draw wider audiences to theatre through its starry cast, but instead became notorious as one of the biggest flops in New York theatre history. The experience matters because it illustrates the daunting gap between screen and stage acting, even for an actor riding high on critical acclaim.

Pfeiffer joined the production fresh from praise for The Fabulous Baker Boys, alongside co-stars including Jeff Goldblum, Gregory Hines and John Amos, but found the lack of retakes on a live stage "unbelievably terrifying". She recalled having to perform night after night even once poor reviews had turned audiences against the show, describing the night after critics' verdicts landed as "devastating", though she still managed to deliver one of her strongest performances of the run. Despite the ordeal, the flop had little lasting effect on her career, as she went on to earn a Best Actress Oscar nomination for The Fabulous Baker Boys, though the experience convinced her to steer clear of Shakespeare thereafter.