English was born in Amarillo, Texas and grew up in Sandy Springs, Georgia. He matriculated at Guilford College in North Carolina on a baseball scholarship, but quit and entered the Culinary Institute of America at the age of 20 and graduated in 1982. He worked under Jean-Jacques Rachou at New York’s La Cote Basque, and then moved to Italy to work at several restaurants there. He returned to the United States at age 25 and served as the Executive Chef of the Italian restaurant Michela’s in Cambridge, Massachusetts for three years before opening the original Olives restaurant in 1989.
In 1998, English partnered with Boston developer James Cafarelli to form The Olive Group, aimed at developing new restaurant properties using English's name and celebrity status. (The new corporation did not include English's existing restaurants.) Although the venture was successful in getting new restaurants off the ground, reviews for some new properties were tepid, and English's existing restaurants began to suffer, culminating in the closure of Olives in 2002 for health department violations. In June, 2002, Cafarelli sued English for non-payment of salary and deferred compensation; on the same day, a major Olive Group creditor also filed suit over the terms of one of its loans. The suit with Cafarelli was eventually settled, with Cafarelli gaining control of one of the group's restaurants, Rustic Kitchen, in Boston's Faneuil Hall Marketplace as well as the rights for a Florida restaurant.
English has been married once, to Olivia English, but they are divorced. They have three children, named Oliver, Isabelle, and Simon.