Flynn tells the often funny and bittersweet story of his Irish Catholic immigrant family and their successes in America. How does he measure up to them? The men, Flynn’s grandfather and father, worked in physically demanding and dangerous jobs as high-rise iron workers helping to create 20th-century New York City. Although some immigrants aspired to be lace-curtain Irish, Flynn’s grandmother and mother kept their families strong and comfortable in loving, blue-collar households. For Flynn, his career on screens and stages and his life as a husband and father, each at times on uncertain paths, have been a departure from and a reaffirmation of his family history.

Fear of Heights is the third solo play by Flynn exploring his family. His earlier one-man play Around the Kitchen Table was directed by Tony Award-winning actor and Tony-nominated director Judith Ivey, who continues to advise him. Flynn is currently co-producing a documentary film about the 1980s Boston comedy scene.