Meet Emma Pittman: Broadway’s rising star who’s breaking the mold, telling her truth, and giving us all the backstage tea in the very first episode of Had to Ask.

Emma Pittman (⁠@emmapittmanofficial⁠) is not just Cherry Valance in The Outsiders — she’s a vlogger, a Broadway scene-stealer, and forever the internet’s Roxie Hart. In this episode, Emma opens up about growing up in Mississippi, storytelling that honors the truth, and what it’s like stepping into a fandom-heavy show like The Outsiders.

We also talk about astrology (obviously), parasocial relationships, Broadway stunt casting, and her dream job as a kid. Plus: the iconic opening night dress she wore to Back to the Future (thank you, Brendan!) and what her For You Page is serving her lately.

Oh — and yes, we do talk about the Search for Dolly.

Tune in for surprising insights, heartfelt moments, and stories only Emma Pittman can deliver.

Chapters:

• 00:09:17 - Emma's Dream as a Kid
• 00:19:57 - The Search for Roxie & The Search for Dolly
• 00:24:21 - Stunt Casting, Especially in the World of Chicago
• 00:28:51 - The Gift of Playing Cherry in The Outsiders

• 00:39:12 - Parasocial Relationships in the Broadway Space
• 00:47:13 - What Emma Hopes for Her Legacy to Be

Follow Had to Ask ⁠@hadtoaskpod⁠ for more bold conversations and unfiltered stories — hosted by Melanie Sutrathada (⁠@melaniesutra⁠)

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

⭐️ If you enjoyed this episode, please leave a review and share it with someone who needs to hear it!

🎭 Meet Emma Pittman: Broadway’s rising star who’s breaking the mold, telling her truth, and giving us all the backstage tea in the very first episode of Had to Ask.

Emma Pittman (@emmapittmanofficial) is not just Cherry Valance in The Outsiders — she’s a vlogger, a Broadway scene-stealer, and forever the internet’s Roxie Hart. In this episode, Emma opens up about growing up in Mississippi, storytelling that honors the truth, and what it’s like stepping into a fandom-heavy show like The Outsiders.

We also talk about astrology (obviously), parasocial relationships, Broadway stunt casting, and her dream job as a kid. Plus: the iconic opening night dress she wore to Back to the Future (thank you, Brendan!) and what her For You Page is serving her lately.

Oh — and yes, we do talk about the Search for Dolly.

Tune in for surprising insights, heartfelt moments, and stories only Emma Pittman can deliver.

Follow Had to Ask at @hadtoaskpod for more bold conversations and unfiltered stories — 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!

⭐️ If you enjoyed this episode, please leave a review and share it with your fellow theatre kids!