The Sondheim Awards are taking place at Old Saybrook High School, and the OSHS “dRAMa” department has fostered four nominees for the award. In Massachusetts and Connecticut, a team of judges attends schools’ musical productions, looking to find the most talented, well-rounded students and directors to nominate for the Steven Sondheim award. At OSHS, Chicago director Nicole Willis was nominated for best direction, and similarly, music director Dr. Jeremy Milton was nominated for best musical direction. Tess Santarsiero was nominated best actress, while Beni Misenti was nominated for best actor.
After the nominations take place, nominees partake in Best Actor and Best Actress boot camp where they work with the Stephen Sondheim Awards team members and special guest artists from NYC. Winners of the Best Actress & Best Actor Awards category will then attend the National High School Musical Theatre Awards. Santarsiero’s initial reaction included a wave of excitement for herself, and a boost of pride for the entire production of Chicago. “I was just so excited and happy that my performance impressed them and got me nominated.” After being nominated, Santarsiero had to attend a boot camp. She describes the boot camp as “a week-long camp where we spend every day rehearsing our medleys and our personal song for adjudication.” A medley is a mix of songs from the show the students got nominated from, in this case: Chicago. She continues by adding, “they judge everyone not only on their talent, but their personalities too. To prepare, I spent almost two weeks rehearsing.”
Misenti had a similar initial reaction of pride for himself and his castmates of Chicago. “I was shocked, but so excited! I was so happy that OSHS was finally getting recognition and was so proud that Chicago could be the show to get to the Sondheim’s.” Misenti, who journeyed his way through the boot camp alongside Santarsiero, describes his transition from a young actor to a more
advanced one. “We got so much coaching and helpful teaching from real Broadway stars and it’s night and day the information that I have in musical theatre from when we started to now.” Both Misenti and Santarsiero agree about the memories and friendships they formed on and off stage during the production of both Little Women, the Fall 2025 play, and Chicago, the Spring 2026 musical.
The process of being nominated for Best Musical Director or Best Director is similar to that of the Best Actress/Actor award. Both Willis and Dr. Milton had similar reactions to being nominated; Willis adds, “Honestly, I was incredibly surprised to be nominated for Best Director, then obviously happy, followed immediately by terribly nervous that only the ‘adults’ would be up for an award. Dr. Milton and I do these awards nights for our students.” After a seemingly successful show, Willis reflects on her ability to have made Chicago what it was: Dazzling. “I am most proud of the moody atmosphere that I pulled out of my brain. The lighting, the sparkles, the set, the costumes, it all helped to create this very monochromatic feel.”
Milton describes a similar feeling; “I was very surprised, then I felt a little guilty because no one else from our production had been nominated yet and I just kept thinking ‘Please have there be more’ and there were!” Milton spent days with the orchestra before finally putting it together to give Chicago the sound. “The first rehearsal with the orchestra is always my favorite – it’s when everything starts to come alive and feel real.”
The students were able to feel the oozing pride coming from both directors, and they expressed that their directors’ support helped them to be nominated. Misenti adds, “Mrs. Willis and Dr. Milton, our director and music director, have been so unbelievably helpful through the process and have been there for me the whole way.” Through the rehearsals, the production, the nomination, and the bootcamp, Santarsiero believes that “they are always helping us to remember what’s really important: doing what we love onstage.”
