At the age of twelve, Stiles started getting involved with theater productions in Portsmouth, New Hampshire. Her first role was when she played the titular character in Annie at the Seacoast Repertory Theater. As a teenager, Stiles played two other major roles while living in New Hampshire: Dorothy in The Wizard of Oz, and Cinderella in Cinderella. Stiles loved the performing arts so much that she spent her summers working at the Prescott ParkArts Festival in Portsmouth. Before she got involved with Broadway productions, she trained at the American Musical and Dramatic Academy in New York City. Stiles is known for her two roles in the Off-Broadway production Avenue Q, which is the story of a college student who moves to New York City with big dreams but lives on Avenue Q and has very little money. Stiles plays Kate Monster and Lucy the Slut, who are two puppets that she controls throughout the show. After Stiles spent much of her time in the production of Avenue Q, she later was offered the role of Joanne in Vanities, a project that Stiles had been involved with for a period of two years. Vanities was located at the Pasadena Playhouse in Pasadena, California, but eventually was moved to Second Stage in New York. This role in Vanities eventually led Stiles to be involved in recording an album for the songs. She played the role of Little Red Riding Hood in Stephen Sondheim and James Lapine's musical Into the Woods at the Delacorte Theater in New York as part of Shakespeare in the Park. She stars opposite Academy Award nominee Amy Adams and Tony Award winners Donna Murphy and Denis O'Hare. In 2017, Stiles appeared in the Epix television series Get Shorty. Stiles appeared in the 2018 film Unsane. She appeared in the stage musical version of the film Tootsie beginning in September 2018, which premiered in Chicago at the Cadillac Palace Theatre from September 11 to October 14, 2018. The musical opened on Broadway in April 2019. In the third season of the Epix television series Get Shorty Stiles character Gladys, a singer/actress, is cast in the Broadway musical Tootsie playing the character Stiles actually played in the musical. This plot development allowed Stiles to recreate one of her numbers from the Broadway show on the TV series.
Discography
Along with having performed on many different stages in various off-Broadway shows, Stiles has found the time to be involved in three different albums for three plays. Her first album recording was singing for the role of Joanne, for the musical, Vanities the Musical. Her second album recording was when she sang the character Nazirah for the musical, The Road to Qatar. Most recently, she can be heard on the album for the musical adaptation of Roald Dahl's James and the Giant Peach as the Spider. Aside from album recordings, Stiles and her friend Howie have been working on their sketches for their comedy channel on YouTube. The YouTube channel is called Sillyocity, and together, the two of them combine their ideas to make short comedic webisodes.
