The Head of Kay’s is a chronicle of the adventures of two boys, Fenn and Kennedy, who conspire to replace their ill-mannered headmaster, Mr. Kay. On the way, the gregarious boys are involved in cricket and rugby matches between the houses, a music concert gone wrong, and other adventures in this exciting story exploring the lives and relationships of boarding school boys.

The book was first serialized in The Captain from October 1904 to March 1905 before being published as a book in 1905. Released in the early part of his prolific career, it is the fifth book by P. G. Wodehouse .