He has performed with several opera companies in the United States, toured with the Los Angeles Philharmonic, and sung in Shanghai and several European cities.
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.
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.
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.
[7] Holiday made his Carnegie Hall debut in October 2012, performing Bernstein's Chichester Psalms with the Atlanta Symphony under Robert Spano.
[8] 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.
[12] 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.
[16] 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.
[18] In November 2015, he joined Parnassus Arts in concert performances of Giovanni Battista Pergolesi's Adriano in Siria in Versailles and Krakow.
[21] He then sang Bernstein's Chichester Psalms on tour with Gustavo Dudamel and the Los Angeles Philharmonic in New York, London, and Paris.
[24][25] 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".
[26] In November 2022 he sang the roles of Man Under the Arch and Hotel Clerk in the world stage premiere of Kevin Puts's The Hours at the Metropolitan Opera.
He has released 3 pop singles, “Alive in Me”, “Waste Mine”, and “Love Finds a Way”, the latter also receiving a remix by Houston-based DJ Riddler.