The Evolution of a Star: Jennifer Diamond OPC '01

Jennifer Diamond (née Rosen) OPC ’01 arrived at Penn Charter in her sophomore year, already a talented actress with a powerful voice. “She sang for me, and I about fell over,” theater teacher Eva Kay Noone said. “I knew she was the real deal. She wanted it and she had the goods.”

“Ms. Noone and Mr. Fitz just completely welcomed me in,” Diamond said. She was in all the PC plays and musicals, plus several in nearby theaters. Noone invited Diamond to be her assistant director for a PC show as a junior, and Diamond directed two one-act plays from David Ives’ All in the Timing for her Senior Comprehensive Project.

Flash forward to 2016 and Diamond has just wrapped up a swath of performances as both Eve and Louise in Ruthless! The Musical at the “Broadway-adjacent” St. Luke’s Theater. She has also had a one-woman show at Feinstein’s/54 Below, directed by Richard Jay-Alexander, who is known for executive producing Miss Saigon, Les Miserables and Phantom of the Opera and co-directs Barbra Streisand.

Prior to that, Diamond toured for two years with mega-star Kristin Chenoweth as a featured member of the cast in Kristin Chenoweth in Concert and The Evolution of a Soprano. “We sang duets together, and I played the tall, leggy brunette to Kristin’s very petite blonde,” Diamond said. With Chenoweth, Diamond sang in the Sydney Opera House, the Hollywood Bowl, Las Vegas at New Year’s, and she made her Carnegie Hall debut.

“I had dreams for my career,” Diamond said, “but that job went bigger and better than any of my dreams.”

So yes, Jennifer Diamond is the real deal.

“I’m proud of what I’ve accomplished, but as an actor, it doesn’t matter what you’ve done — when you walk into an audition, you’re still at square one,” Diamond said. “You’re only as good as your last job, and it could all come tumbling down.”

Diamond was recently in London for a week with her husband, Robert, to see shows and catch up with old friends. Robert Diamond is the chief executive officer and editor-in-chief of, the largest theater website in the world. The duo married – dramatically! – in 2011 as the wind and waves of Hurricane Irene battered Manhattan.

Diamond, who is auditioning for whatever might be next, works hard, takes a lot of classes to keep learning and growing, and takes time to appreciate her life. “My husband and I just moved to our lake house full time, giving up our apartment in the city. It’s incredible to have the best of both worlds – I go into New York City to audition, and I come home and sit on the dock with my dogs and my feet in the lake.”