Barry Connolly was born and raised in Worcester, MA. The third of eight children, Connolly found space for himself in a crowded household by drawing from a young age. He graduated from high school and began painting, while completing classes in painting and illustration at Worcester Art Museum and Fanning Trade School.
From 1991 to 1993, he co-operated Parabelleza Gallery on Prescott Street, which showcased local artists. From 1997 to 2000, he lived in New York City and exhibited his work throughout Manhattan. While continuing to paint, he is employed as a diesel mechanic in Worcester, where he lives with his wife and two sons.