A trained singer, Krakowski has made numerous appearances on stage. At age 18 she originated the role of Dinah the Dining Car in the 1987 Broadway production of "Starlight Express". She appeared in the 1989 Broadway musical "Grand Hotel" as the typist and would-be-movie-star Flaemmchen, for which she was nominated for a Tony Award. Her solo number "I Want to go to Hollywood" is included on the original cast recording. At the 2000 American Comedy Awards, Krakowski won rave reviews when she performed a sexually-charged musical tribute and love letter to Microsoft chairman, Bill Gates.