In it, Rupp portrayed Mae Sister Woman. Rupp continued to devote herself to acting full-time through the s and performed in numerous regional stage productions. Directed by Wynn Handman and sharing the stage with Rita Jenrette, Rupp's performance as Cynthia was immortalized by legendary caricaturist Al Hirschfeld and described in a New York Times review as "an appealing mixture of pluck and pathos. She frequently performed on stage and appeared in commercials before winning her first television role in as Sheila, a topless dancer, on the daytime drama All My Children. She originated the role of Cynthia in , a character based on Heimel's observations made during her stints as a columnist for Playboy and The Village Voice.