Springfield Little Theatre alum Kim Crosby was appearing in A LITTLE NIGHT MUSIC at the Berkshire Theatre Festival while composer Stephen Sondheim was crafting a new musical weaving together classic fairy tale characters. When a casting director scouted Crosby, she exuded the qualities Sondheim had envisioned for a new ingenue role. After five auditions, Crosby was crowned Cinderella in Sondheim’s exciting new work, INTO THE WOODS.

Before crossing paths, Crosby had previously appeared on Broadway in JERRY’S GIRLS – a send up to another musical theatre great, Jerry Herman. Sondheim had already emerged as a musical theatre titan with hits like SWEENEY TODD, SUNDAY IN THE PARK WITH GEORGE, WEST SIDE STORY, and GYPSY.

“Once you get past the fact that you’re working with a god like Stephen Sondheim, everybody gets down to work. He was tremendously accessible,” Crosby explained. “Obviously, we were all in this together and it was imperative that he be able to [make changes]. I was constantly getting notes from him. I even saved a lot of the little, square, post-it sized notes that he wrote out when he would watch the show.”

INTO THE WOODS was still very much in progress when the cast and creative team met in San Diego at the Old Globe Theatre. Creating a brand-new show with Sondheim and legendary director James Lapine was intense work that required every bit of Crosby’s signature professionalism and focus. Much of the rehearsal process was a whirlwind as Sondheim and Lapine molded the complex ensemble narrative into a cohesive whole.

“Much changed in the process,” Crosby revealed. “We would have entirely new songs go in one night that were not there the day before, changing lyrics, changing blocking, jumbling scenes. It’s like everything gets pixelated and then it comes back together again. It was very intimidating at first, obviously, to be working with Sondheim. But that quickly vanished, especially when we were in the trenches trying to implement every change they made and make it the best it could be.”

With characters shifting, scenes moving, songs being inserted and removed, the cast and crew had to remain fully focused. One notable change Crosby recalled was the Narrator played the Wolf in an early rendition, but later the Wolf was reassigned to the Prince Charming actor. Some of the updates blurred together in the chaos of rehearsals, but one special addition remains crystal clear in Crosby’s mind.

“I’ll just never forget, my favorite moment was when Steve Sondheim came in. We were all pulled into the rehearsal room because he had a new song that he wanted to put in called ‘No One is Alone,’” Crosby reminisced about her character’s tender ballad near the close of the show. “So, I have a recording of him singing, ‘No One is Alone.’ That I got to sing that first was a tremendous privilege. I’m just so proud of that.”

INTO THE WOODS is known for its lush sets and elaborate costumes, but at its heart, the story explores the joys and heartbreak of relationships and parenting. Crosby didn’t yet know that the show would become deeply engrained in the throughline of her own family.

Enter Prince Charming. When INTO THE WOODS moved to New York, Robert Westenberg stepped in to originate the dual role of Prince Charming/The Wolf on Broadway and would later earn a Tony nomination for his performance. Crosby and Westenberg married and had three children together.

Increasing her ties to the legacy of INTO THE WOODS, her father, Don Crosby, eventually closed his dental practice here in Springfield to pursue his own passion for acting. Despite starting later in life than his daughter, his career was a success, and he earned his first equity card in the national tour of INTO THE WOODS as Cinderella’s Father.

“[INTO THE WOODS] just gave me my life. It gave me all the things that are important to me,” Crosby reflected. “I will forever be grateful to have been cast in that. To James Lapine and Stephen Sondheim. What a rarefied air to get to breathe for a while.”

The full circle moment began many years back when Crosby’s father introduced her to Springfield Little Theatre and she was instantly smitten with the stage. At five years old, Crosby sang in the children’s chorus of THE KING AND I. The production was a true family affair as her father played the role of Lun Tha and her brother and sister were also in the cast.

“Every once in a while, in some shows, you’ll just get this little pang of pure joy,” Crosby recalled of being on the Landers stage. “I just had that so many times there where I think, ‘Gee, I love what I do. I love this.’ It’s magic. It’s really magical to hear the strings of a live orchestra playing an overture. It’s thrilling and terrifying and really fun at the same time.”

Her mother, Donna, was a mainstay behind the scenes throughout Crosby’s many seasons performing at the Landers.

“Mom was always involved in some way or other. If she wasn’t sewing costumes, she was running the box office or serving on the board. Doing anything and everything,” Crosby remembered. “She’s the epitome of a volunteer. In a community theatre like that, it’s absolutely required to make it run. She was just full of all that passion.”

Growing up, Crosby maintained ties to the Landers Theatre, including a successful bid for America’s Junior Miss which was hosted at the historic location. Crosby attributes her ultimate success in the competition to her familiarity with the location.

“When I was in high school, I was in the America’s Junior Miss pageant, and it was onstage at the Landers. I have to say I think it gave me an unfair advantage,” she laughed. “I just felt at home. I was at home. I had been down in those dressing rooms. I had climbed up those stairs from the basement hundreds of times.”

From a young age, Crosby felt confident that the theatre would be her future. She moved to New York to attend the Manhattan School of Music studying opera, but her heart told her that musical theatre was her true calling. Ever since her earliest experiences at SLT, she felt happiest in a musical.

“I’ve just felt really privileged to have [SLT] available to me,” Crosby professed. “Had I not lived in this community or had Little Theatre, I don’t know what else I would have done. Whether I would have found my way into the profession that I eventually had if not for that. It’s just a rare and wonderful thing.”

Success bloomed early for the talented vocalist. Credits stacked up including GUYS AND DOLLS on Broadway, MY FAIR LADY at the Muny, and national tours of OKLAHOMA! and PETER PAN. Although she was booking top tier professional gigs, Crosby never forgot her home stage and returned to Springfield Little Theatre in guest roles over the years in MY FAIR LADY, MARY POPPINS, MAMMA MIA!, and even INTO THE WOODS. Crosby said it was no question that any time she was invited back, she was excited for the opportunity.

“The [SLT] productions are always so first rate. It’s not just the talent that’s on stage, but it’s production value and just the commitment to the art form. It’s just so rare,” she praised. “What Little Theatre has been and means to the community. There are so many people to commend for keeping it up and running and maintaining the quality of what is constantly presented. It’s why people passionately support it. It’s a gem. It’s a real gift to humanity.”

Crosby remained close with her family, but she credits her husband with steering them back toward Springfield where they settled for more than a decade after years in New York and Colorado. Westenberg moved the family to Missouri to lead the respected theatre programs at Drury University and Missouri State University. The move opened Crosby to more opportunities to perform live for her hometown.

Crosby praised the growth she’s seen in SLT’s programming, particularly for students. She is an advocate for the arts and the skills that are formed through learning live theatre.

“I have to say, just the strength of the programs for kids, what that has bred in the community and what talent has come out of that because of the great instruction and consistency. It’s such a rare thing,” Crosby admired. “Especially now where most people only venture in that tiny little phone. You have so few opportunities to put it down and actually be live opposite someone else and be able to express yourself in person. It’s just awful that that’s a very rare thing, but I think that’s why we love it so much and how important that is to connect to people live. It gives us courage. You overcome your fears, you walk on stage, you say your lines until the jitters in your voice subside, and it’s a victory to be able to get out there and tell a story and to be brave. It’s just so gratifying.”

After a lifetime of being tied to Springfield Little Theatre and INTO THE WOODS, Crosby still cherishes both.

“INTO THE WOODS is woven into our family,” Crosby declared. “My brother, Craig, played Jack the first time that they produced INTO THE WOODS at Little Theatre. [SLT] was my life and my haven and my happy place for all the while we were there and remains so. When and if I ever get another opportunity, I would gladly come back and work there again.”

Explore audition opportunities this season at Springfield Little Theatre.