Tommy O'Brien and Meghan Kessel Photo by CM Stage Photography

Premiering in 1972, Pippin tells the story of Charlemagne's (Stan Austin) son, Pippin (Tommy O'Brien). Pippin has recently graduated from university and has returned home to embark on a journey to find his "corner of the sky." Told as a show within a show, the story is presented by a performance troupe that evokes a traveling minstrel group of the Middle Ages. Pippin seeks guidance from various figures and tries out a number of paths to find meaning in his life–from war to pleasure to domesticity–while being led (and manipulated) by the troupe's enigmatic Leading Player (Asia Posey). Even when he seems to have found happiness in the home of Catherine (Meghan Kessel), a kind widow, and her son, Theo (an adorable Evelyn Dorough), the allure of something "more" continues to tempt Pippin until the Leading Player presents him with the ultimate dramatic choice.

I love Pippin, and the BrightSide Theatre in Naperville has added a layer of quaint suburban charm to this classic piece. I continue to be amazed by the caliber of talent found across the Chicagoland theatre scene, and both O'Brien and Posey are particularly strong standouts. Posey–remarkably making her musical theatre debut–commands the stage with her powerful vocals and an expressiveness that shifts effortlessly between cheerfully engaging and subtly sinister. Her Leading Player radiates charisma and danger in equal measure. O'Brien, meanwhile, brings both mesmerizing vocal finesse and emotional range to the role of Pippin, embodying the character's innocence, idealism, and growing frustration with the life around him.

The ensemble–as members of the theatrical troupe–moves seamlessly among multiple characters, providing energy and cohesion throughout. Two standouts are the oldest characters of the show, Austin's Charles (father) and Cheryl Newman as Berthe (grandmother). Austin delivers a suitably commanding Charles, and the father-son dynamic with Pippin feels genuine and grounded. Cheryl Newman, who not only plays Berthe but also designed the production's costumes, brings great vitality and humor to her scene-stealing number, offering Pippin (and the audience) sage advice about savoring life's fleeting joys. Finally, Meghan Kessel brings warmth and heart to Catherine, the widow who helps Pippin glimpse a different kind of fulfillment in Act II. Her sincerity makes their relationship arc feel grounded and touching.

Director Jeffrey Cass and his creative team successfully bring this life-lesson-laden musical to the western suburbs, delivering both entertainment and thoughtfulness. The hard working ensemble sings and dances their hearts out to the catchy songs of Stephen Schwartz, giving the audience an entertaining night out.

If you find yourself in the direction of Naperville in the next few weeks and are looking for an entertaining and thoughtful diversion, make a stop at the BrightSide Theatre to see Pippin.

Pippin runs through June 29, 2025, at BrightSide Theatre, Meiley-Swallow Hall, 31 S. Ellsworth, Naperville IL. For tickets and information, please visit brightsidetheatre.com