Antonio Cipriano was raised in Grosse Pointe, Michigan, in Metro Detroit. There, he attended University Liggett School from which he graduated in 2018. He was involved in numerous local and school theatre productions and was a member of the Michigan Opera Theatre Children's Chorus.[citation needed]
Cipriano's career began as a high schooler. He first found acclaim as the winner of the Sutton Foster Ovation Awards for Best Actor in May 2017 for his performance as Mickey McKee in Hello! My Baby; the award recognizes "outstanding achievement in individual artistry, vocal, dance and acting performances for a male lead in a high school musical theatre production." As a result, he represented Michigan at the 2017 National High School Musical Theater Awards (also known as the Jimmy Awards) and placed in the top four finalists out of the thirty-six male competitors.
In 2018, he was cast in the original Cambridge, Massachusetts, production of the musical Jagged Little Pill, inspired by the album of the same name by Alanis Morissette. The production played at American Repertory Theater for two-and-a-half months. In January 2019, it was announced the show would transfer to Broadway. In the interim, Cipriano appeared in a one-week Off-Broadway production of Carmelina at the York Theatre that same month. He also took part in the original reading of the stage adaption of The Notebook, with music by Ingrid Michaelson. Following previews of Jagged Little Pill, the production opened on Broadway in December 2019. The musical was nominated for fifteen Tony Awards, winning two. The production was paused in March 2020 due to the COVID-19 pandemic. Cipriano did not rejoin the production in September 2021 due in part to his stance on the controversy surrounding the musical's main character Jo, whose gender was changed from non-binary to cisgender for the Broadway version.

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