He graduated from Kingswood-Oxford School in West Hartford, Connecticut and his near-perfect SAT scores (796 Verbal & 793 Math) earned him a scholarship to Yale University.
While a student at Yale College in 1974, he was a test subject in a controlled study on the addictive nature of computer games, which at that time were text-based.
In 1999, McEnroe wrote an often-cited[4][better source needed][5][failed verification] essay for McSweeney's in which he claimed to be book critic Michiko Kakutani.
[7] McEnroe has been a contributing editor at Best Life[8] and Men's Health magazines and has been a frequent contributor to Mirabella, Mademoiselle and Verge.
McEnroe has moderated the Connecticut Forum[19] for a record-setting ten times, including a panel[20] featuring Anthony Bourdain, Alice Waters and Duff Goldman.
In 2017, McEnroe teamed up with Kuan and director Eric Ort to create a series of monologues juxtaposed with the movements of Liszt's "Faust."
[23] In 2016, the Colin McEnroe Show won First Place in the Interview category of the Public Radio News Directors awards, for his hour-long conversation with Hal Holbrook.