Holiday was born in 1985 in the city of Rosenberg in Fort Bend County, Texas, to John Holiday, Sr, a welder and Waverly A. Holiday a homemaker who sang and played clarinet. His maternal grandmother, Sandra Mathis Franklin, was the pianist and music director at Missionary Baptist Church. He taught himself to play piano by imitating her, and later the organ. While only 6 or 7 years old he sang solos in church and at Travis Elementary School. He won a spot in the Fort Bend Boys Choir, which led to appearances as a treble soloist in the Houston Symphony‘s performances of Berlioz’s La Damnation de Faust with Denyce Graves in the role of Marguérite. He later said: “I’d never seen anyone who looked like me doing what she did. I’d never thought of being an opera singer. To tell the truth, I didn’t know that world even existed. I decided that was what I wanted to do.”
Holiday graduated from Lamar Consolidated High School in Rosenberg, Texas. For two of his high school years he was the first chair tenor in the All-State Mixed Choir sponsored by the Texas Music Educators Association. The University Interscholastic League designated him one of the Most Outstanding Performers in Texas.
He studied at Southern Methodist University (SMU) from 2003 to 2007, earning a bachelor of music degree in vocal performance. While a student at SMU, he won first place at the TEXOMA region of the National Association of Teachers of Singing several times. Though SMU presented few performance opportunities for a countertenor, in 2005 he did sing the role of Gherardino in the school’s production of Puccini‘s Gianni Schicchi. He won the Concerto Competition SMU’s Meadows School of the Arts in 2007.
He spent the academic year 2007–2008 studying voice at Indiana University‘s Jacobs School of Music. He then returned to Rosenberg and taught Choral Music and Voice at Lamar Junior High School and Lamar Consolidated High School from August 2008 to December 2009. He returned to vocal studies, now at the University of Cincinnati College-Conservatory of Music where he earned a master’s degree in vocal performance in 2012. There he performed the role of Tolomeo in Handel‘s Giulio Cesare in Egitto under conductor Mark Gibson. In May 2011, he took first place in the Dallas Opera Guild Competition. He spent the summer of that year with the Santa Fe Opera Apprentice program for singers.
He next enrolled at Juilliard, studied with Marlena Malas and Stephen Wadsworth, and obtained his Artist Diploma in Opera Studies in 2014.
He later said his models in the countertenor repertoire were Andreas Scholl and Derek Lee Ragin.
Holiday made his Carnegie Hall debut in October 2012, performing Bernstein’s Chichester Psalms with the Atlanta Symphony under Robert Spano. He made his debut at Portland Opera in the role of 1st Oracle and 1st Cardinal in Kevin Newbury’s 2012 production of Galileo Galilei by Philip Glass under the baton of maestra Anne Manson. He reprised those roles in his 2013 debut at the Cincinnati Opera.
In 2013 he took on the title role in the James Darrah production of Radamisto at the Juilliard School. At Wolf Trap Opera that year he performed the title role in Giulio Cesare in Egitto. In 2014, he also made his Los Angeles Opera debut as the Sorceress in the Barrie Kosky production of Henry Purcell‘s Dido and Aeneas.
In 2015, he originated the role of Male Soloist No. 1 in the world premiere of Huang Ruo‘s Paradise Interrupted at the Spoleto Festival USA, a role he repeated in New York at the Lincoln Center Festival in 2016 and in Shanghai for the Art Macau Festival.
At the Glimmerglass Festival in the summer of 2015, he sang the role of Giulio Cesare in Tazewell Thompson‘s production of Antonio Vivaldi‘s Catone in Utica. He returned to sing the title role in Handel‘s Xerxes in the summer of 2017. In November 2015, he joined Parnassus Arts in concert performances of Giovanni Battista Pergolesi‘s Adriano in Siria in Versailles and Krakow.
In January 2017, he won the Marian Anderson Vocal Award. In September 2017, he sang in the Opera Philadelphia world premiere of Daniel Bernard Roumain‘s chamber opera We Shall Not Be Moved. He repeated that performance at the Dutch National Opera in March 2018, his European debut. He then sang Bernstein‘s Chichester Psalms on tour with Gustavo Dudamel and the Los Angeles Philharmonic in New York, London, and Paris.
In December 2019 he performed the alto part in Handel’s Messiah with the Lucerne Symphony Orchestra.
In February 2020 he sang in the world premiere of Matthew Aucoin’s Eurydice at the Los Angeles Opera.] He is scheduled to make his Metropolitan Opera debut in that opera in December 2021.
Though the COVID-19 pandemic forced the cancellation of many of his scheduled performances, his recital at New York’s Metropolitan Museum of Art was presented as a virtual concert. Holiday combined Italian baroque arias with works by Black composers in conjunction with the museum’s exhibit of paintings by Jacob Lawrence called “The American Struggle”.
Holiday has been an Assistant Professor of Music at the Conservatory of Music at Lawrence University since 2017. He previously taught at the Ithaca College School of Music. He is a member of the National Association of Teachers of Singing (NATS) and the American Guild of Musical Artists (AGMA).]