Since winning The Dallas Opera’s 2011 National Vocal Competition, the countertenor’s successes in opera have ranged from Handel’s Xerxes (Glimmerglass Festival) and Purcell’s Dido and Aeneas (LA Opera) to Philip Glass’s Galileo Galilei (Portland Opera, Holiday’s operatic stage debut), Matthew Aucoin’s Eurydice (LA Opera, world premiere), Jonathan Dove’s Flight (Des Moines and Utah operas), Daniel Roumain’s We Shall Not Be Moved (world premiere at Opera Philadelphia, reprised for the singer’s European debut with the Dutch National Opera), and Huang Ruo’s Paradise Interrupted (Shanghai’s Macau Arts Festival). In the latter, Holiday sang the First Male Voice, a role he created in the 2016 Spoleto Festival world premiere. Recent seasons have brought appearances at La Jolla Music Festival and the Metropolitan Museum of Art in a recital curated as part of the Jacob Lawrence “Struggle Series.” Other performances taken place at such venues as the Kennedy Center, the legendary Apollo Theater, The Sorting Room in Beverly Hills, and Trinity Wall Street, as well as Houston’s Ars Lyrica, the University Musical Society in Ann Arbor, London’s Barbican Centre, and Taiwan’s National Kaohsiung Center for the Arts. Holiday has toured with Gustavo Dudamel and the Los Angeles Philharmonic singing Bernstein’s Chichester Psalms and has performed with the Saint Paul Chamber Orchestra, the Cincinnati Chamber Orchestra, and the Nashville Symphony.