Christopher Hollyday began performing publicly in 1983 in the Boston area at age thirteen as a member of his brother Richard’s quintet. In 1988 Hollyday headlined a week at the historic Village Vanguard in New York City. Hollyday toured with Maynard Ferguson as a featured soloist in the trumpeter’s “60th Birthday Big Band”, and was featured on the Maynard Ferguson “Big Bop Nouveau” album. From 1989 through 1993, Hollyday toured with his own quartet visiting every Western European country, Brazil, Canada, and most of the United States. During this period Hollyday made four recordings for RCA records. As Hollyday toured he visited local schools as an effective clinician and became interested in music education.

In 1993 Hollyday pursued his desire to teach and study composition and arranging at Berklee College of Music in Boston, MA. It was here that he began studying the clarinet.

In 1996, Hollyday relocated to San Diego where he taught high school instrumental music for 13 years. Hollyday completed a masters degree in jazz studies at San Diego State University where began studying flute.

He now teaches saxophone at San Diego State University and woodwinds privately from his studio in San Diego. In 2018 Hollyday returned to the recording studio to record his critically acclaimed comeback album Telepathy. He recently recorded Dialogue-a follow-up album with The Telepathy Quintet, releasing in August 2019. Mr. Hollyday currently performs in San Diego and throughout Southern California, as a jazz saxophone soloist, and with his Telepathy Quintet.