John Cherry was educated at Keighley Boys' Grammar School, from 1916 to 1924, then went to Manchester University to study English (with French and Latin as subsidiary subjects).

He gained his BA (Hons) in 1927, but stayed on a further year to do a post-graduate course, emerging in 1928 with a Manchester University Teaching Diploma, and his Board of Education Certificate.

Wallasey Grammar School was his first teaching post, from 1st September, 1928, but after only three years he moved to the South Shields High School, which he joined on 1st September, 1931.

He transferred to Harton as Senior English Master, but he also taught games where he was something of an accomplished Rugby hooker for Westoe rugby team.

In April, 1944, he moved to Middlesborough High School as Senior English Master.