Raised in Los Angeles, California, D’Alessandro was the youngest of three brothers. When art competition was a form of play for the brothers, it later grew to his obsession. D’Alessandro attended the Art Institute of California where he explored mixing mediums as well as digital. He also attended Illustration, Sculpting, and Fine Art workshops in Fullerton Ca. After spending long periods of time studying different techniques, D’Alessandro's art became increasingly influenced by artists from the early 1900s. During D’Alessandro’s studies, he painted many different themes. He painted with restless intensity, often painting from morning until night. D’Alessandro was able to indulge his earliest artistic preferences for people, nature, architecture, and landscapes in his illustration and personal pieces. He also painted family, friends, and gardens. He has done commissioned work for a variety of clients in music publishing and editorial. His work has been exhibited in numerous private and public collections.