After graduating college, Oh was cast to play Marisol in the 2013 off-off-Broadway comedy play Frankenstein Upstairs and assorted characters in the 2015 American premiere of Lucy Kirkwood's Chimerica at the Studio Theatre in Washington, D.C. In 2016, they had a role in the film How to Be Single, and in the threatre, they played a Dandy Minion in the premiere of A 24-Decade History of Popular Music and Number Four, a comfort woman, in Hansol Jung's Among the Dead.
From 2014 to 2017, Oh staged My Lingerie Play (stylized as {my lingerie play}), a series of 10 art/performance installations at public areas and small theatres in New York and Washington D.C., as well as on the internet. In the initial eight performances, Oh stood on a soapbox wearing just their underwear, a black hat, and sunglasses, holding two brown paper bags on which they had written about slut-shaming, street harassment, and violence against women. Some performances involved additional people, and Oh invited spectator participation at the installations. These concluded in October 2017 with a concert performance, titled {my lingerie play} 2017: Installation #9: THE CONCERT AND CALL TO ARMS!!!!!!!!!, the final installation, at the Rattlestick Playwrights Theater in New York, with final outdoor performance (Installation 10/10 (The FINAL Final Installation)) scheduled afterwards at Washington Square Park.
The concert performance was just under two hours long and featured music performed by Oh and their band; The New York Times descried the show as "more of an indie band concert" than a traditional play. The show began with Oh in a bathrobe on a soapbox with paper bags inviting the audience to write messages on their own bags. Audience members were given bubble wands to blow during the performance and invited to dress up with body glitter, temporary tattoos, jewelry and other cosmetics at a "shimmer station". As the show went on, Oh undressed to reveal their "mostly shoplifted" underwear and discussed their life, human sexuality and sexual harassment, gender, race and racism, transphobia, and current events including the Pulse nightclub shooting and the 2016 United States presidential election. A central theme being liberation, Oh also went topless, held what the Time Out New York magazine termed a "funny and genuinely erotic" discussion about consent with an audience member they made out with, and invited other audience members to have their heads shaved on stage. The show ended with audience members standing around the edge of the theatre, holding the brown paper bags they themselves had written on earlier.
In early 2018, Oh began planning an additional performance of My Lingerie Play, this time in Massachusetts, at the invitation of the director of the American Repertory Theater. However, after talking with a spiritual counselor, Oh decided to stop performing the play, and was instead offered a residency at the theatre. The five installations they produced, Clairvoyance, began in October 2018 and was scheduled to run through April 2019. It involved, among other activities, staging "Chosen Family Portraits" with the audience and planting trees at Harvard University. Also in 2018 and 2019, they played Devon in the webseries Queering and Gretchen in the play Georgia Mertching is Dead, acted in a tour of Parable of the Sower, and participated in The Public Theater's Emerging Writer's Group. While at The Public Theatre, Oh developed and first performed their play My H8 Letter to the Gr8 American Theatre. Oh and the cast returned in 2020 to perform the play on Zoom for the Ma-Yi Theater Company, where Oh was a writer.
Oh's best-known works also included The Infinite Love Party, described as "all-night slumber party at the off-off-Broadway Bushwick Starr that contained a potluck, dance party, a working swing, an open mic, and live music from Oh". In 2022, they were awarded a Helen Merrill Award for Playwriting by The New York Community Trust. For the 2024 Breaking the Binary Theatre Festival, Oh wrote and directed the play A Rare Bird. Oh and playwright Lloyd Suh were commissioned by the Ma-Yi Theater Company in 2023 to write a musical titled The Science Fair Project, which was still in progress at the time of Oh's death.
Diana Oh has written 1 shows including {my lingerie play} 2017: THE CONCERT AND CALL TO ARMS!!!!!!!!! The Final Installation (Playwright).
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