Tony Award winner Matt Doyle (@mattfdoyle) — who you may know from Company, Spring Awakening, The Book of Mormon, and more — joins me on Had to Ask for a candid, hilarious, and heartfelt conversation about the highs, lows, and everything in between of life in the theatre. From falling head over heels for Sondheim to dreaming of playing Romeo, Matt shares how perseverance—not perfection—has carried him through an industry that never really gets easier.

We dive into mental health, imposter syndrome, and the self-sabotage that comes with being an “insecure mess,” plus his deep admiration for Audra McDonald, Joy Woods, and Gavin Creel. Matt opens up about Conversations with Mother, why building a life outside the work matters, and the joy (and nerves) behind stepping into Jay Gatsby’s shoes in The Great Gatsby.

Also on the table? Our mutual agreement that we’d both be terrible in jail, the unlikely way he met Bonnie Milligan, and his voice talent crush. Whether you’re here for the Broadway stories, the Gatsby gossip, or just to feel a little less alone in chasing big dreams, this one’s got it all.

Chapters:
02:41 Gossip Girl — and whether he’d choose Blair or Serena08:17 The first time Matt met Gavin Creel10:36 High school backstage on Spring Awakening13:23 Thinking he was done after The Book of Mormon18:18 His friendship with Bonnie Milligan25:23 The Broadway revival he’d like to see28:23 Falling in love with musical theatre through Sondheim31:59 Imposter syndrome and winning a Tony37:24 The pressure to bring Broadway back with Company45:40 The chicken soup for the soul that was Conversations with Mother49:09 Opening The Great Gatsby in South Korea

Follow Matt Doyle (@mattfdoyle) and Had to Ask (@hadtoaskpod) for more bold, unfiltered conversations — hosted by Melanie Sutrathada.

Co-produced and edited by Joseph Loper. Special thanks to The Chatwal in NYC for being the home of Had to Ask for Season 1!

⭐️ Loved the episode? Leave a review and share it with a friend who loves big laughs and bigger dreams.