Season 6, Episode 4 - Love, Broadway, and The C.H.E.S.S. Board feat. Chester Gregory

The BIG We

In this inspiring episode, Broadway actor and singer Chester Gregory shares his journey from Gary, Indiana, to the bright lights of Broadway. He opens up about how his hometown and icons like Michael Jackson fueled his passion for the stage and how his love for singing and acting developed over time. Chester also reflects on his mother’s constructive guidance and the invaluable lessons she taught him, both in life and in music.

As a performer and coach, Chester emphasizes the power of listening to oneself, to the art, and to others. He describes how storytelling and teaching are intertwined and how helping others find their voice has become a significant part of his purpose. Chester also gives us a glimpse of his latest project, The C.H.E.S.S. Board, and his upcoming album, while recounting the thrilling moment when his talent was discovered, leading him from the Apollo Theater to Broadway.

This episode is a deep dive into love for music, for teaching, and for making meaningful connections through art.

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