Born in 1972 in New Haven, Connecticut, Hollyday grew up listening to his father's extensive jazz record collection. Influenced by Charlie Parker, he started playing the alto saxophone at age nine and by 1983 was joining his older brother Richard Hollyday, a trumpet player, on gigs in the Boston area. In 1985, he released a self-produced album, Treaty, which featured bassist Nat Reeves, drummer Ron Savage, and a young John Medeski on piano. A sophomore outing, Reverence, arrived in 1988 and found Hollyday backed by a veteran rhythm section with pianist Cedar Walton, bassist Ron Carter, and drummer Billy Higgins. Also that year, he came to wider recognition headlining a weeklong stint at New York's Village Vanguard and touring with Maynard Ferguson.
Buoyed by the attention, Hollyday signed with RCA/Novus and in 1989 made his debut for the label with the album Christopher Hollyday, a quintet date with trumpeter Wallace Roney. Between extensive touring that took him around the globe, he continued to record for RCA, issuing the 1990 quartet album On Course with pianist Larry Goldings, as well as 1991's The Natural Moment with pianist Brad Mehldau. He rounded out this period with 1992's lushly produced And I'll Sing Once More, which featured a 14-piece band including saxophonist Scott Robinson, pianist Kenny Werner, and violinist Mark Feldman.
While touring and giving clinics, Hollyday grew increasingly interested in education. In 1993, he decided to take a step back from performing to pursue his teaching degree, studying composition and arranging at Boston's Berklee College of Music. From there, he relocated to San Diego and spent the next decade as a high school music teacher. He also earned his master's degree in Jazz Studies at San Diego State University, where he eventually accepted a teaching position on the school faculty. Though teaching occupied much of his time from the late '90s onwards, he continued to perform on a local level.
In 2018, Hollyday returned to regular gigging with the release of Telepathy, his first studio album in over 20 years. The record found him working with longtime associate Gilbert Castellanos, a San Diego trumpeter. Hollyday and his Telepathy Quintet quickly returned with 2020's Dialogue. ~ Matt Collar, Rovi