Cunningham graduated from Regis High School[3] in Denver 1927 at age fifteen, showing great skills in Latin and Greek.
In high school, he first corresponded with Yvor Winters who was then a graduate student at Stanford University and who later became an influential poet and critic.
As a teacher and critic, Cunningham often concentrated on Shakespeare and the English Renaissance, authoring works such as Woe or Wonder: The Emotional Effect of Shakespearean Tragedy.
[8] Cunningham's epigrams (including his translations of the Latin poet Martial) and short poems were often witty and sometimes ribald.
He was one of a small number of modern writers to treat the epigram in its full, classical sense: a short, direct poem, not necessarily satirical, dealing with subjects from the whole range of personal experience.
[9] Cunningham's longer poems "tend toward the epigrammatical, little quotable bits that express thoughts with exceptional neatness.
"[10] His plain-spoken lyrics about love, sex, loss, and the American West are especially haunting and original, but he was also capable of investing abstract ideas--both mathematical and philosophical--with considerable emotional force.
Cunningham "inclined toward logical statement and syllogistic argument, saying so much in so little space, often in a single iambic pentameter couplet.