Gwon made his off-Broadway debut in 2009 with
Ordinary Days, the first musical production in
Roundabout Theatre Company's black box space, Roundabout Underground. In 2011,
Signature Theatre in Arlington, Virginia, premiered Gwon's musical
The Boy Detective Fails, based on the
novel by Joe Meno, as part of their American Musical Voices Project.
South Coast Repertory commissioned and premiered his musical
Cloudlands, written with Octavio Solis, in 2012. In 2015, Gwon had two simultaneous world premieres, both co-written with
Julia Jordan:
Bernice Bobs Her Hair, adapted from the
F. Scott Fitzgerald short story, at the Lyric Theatre of Oklahoma, and
Cake Off at Signature Theatre in Arlington, Virginia.
Cake Off received a
Helen Hayes Award nomination for Outstanding Original Play or Musical Adaptation.
Village Theatre in Issaquah, Washington, produced the world premiere of Gwon's musical
String, with a book by Sarah Hammond, in 2018. Gwon's
Ordinary Days was preserved on a cast album and has been produced in London's West End and around the world from Paris to Rio de Janeiro. A 2018 revival by the Keen Company was nominated for a
Drama League Award for Best Revival of a Broadway or Off-Broadway Musical. Gwon's song "I'll Be Here" was recorded by
Audra McDonald on her album
Go Back Home. McDonald has performed the song in concert, including at Carnegie Hall and Lincoln Center. It aired on PBS's Live from Lincoln Center in 2013. He served a three-year term on the Tony Awards Nominating Committee, beginning in 2015. Gwon's musical
Scotland, PA, with book by
Michael Mitnick, adapted from the cult 2001
film, premiered at Roundabout Theatre Company's Laura Pels Theatre in 2019. Gwon's musical ''All the World's a Stage'' premiered at Keen Company in 2025, and subsequently released a cast recording. == Honors ==