Born in Queens and raised in the borough's middle class Forest Hills, Romano went to high school with Fran Drescher. After graduating in 1975, he worked at various jobs (gas station attendant, bank teller, futon deliveryman) while dabbling in comedy, making appearances at open mike nights at various clubs. In 1987, he decided to pursue stand-up full-time. Two years later he won $10,000 and priceless exposure in a New York comedy contest that jump-started his career. After his appearance with Johnny Carson, Romano was featured in HBO's "The 15th Annual Young Comedians Festival—hosted by Dana Carvey"—and went on to perform in several other comedy showcases.