Kennedy frequently appeared in the original cast of the short-lived "Side Show" as the standby for Emily Skinner. She has also starred in "Monty Python's Spamalot" on Broadway as a replacement for the Lady of the Lake. She has been seen on Broadway in "Les Misérables", "Sunset Boulevard" with Glenn Close, "Side Show", and "Cinderella" with the New York City Opera. She originated the role of Cathy in Jason Robert Brown's "The Last Five Years" in its Chicago premiere, but opted to do "South Pacific" at the National Theatre in London instead of following the show Off-Broadway (she was replaced by Sherie Rene Scott). In 2004, she starred as Emma Carew in the concert-style version of Jekyll & Hyde – The Musical entitled Resurrection, opposite Kate Shindle and Rob Evan. However, she left the tour before it concluded, to be replaced by Brandi Burkhardt, who is heard on the recording of the tour.