Neal Gladstone grew up in a musical household where everyone in the family played the piano. He studied violin as well, and performed with his high school symphony in Stillwater, Oklahoma, but it was the era of folk music, so Neal learned to play the guitar in his junior year, and spent the next nine months copying rock and roll songs from records and getting award-winning callouses from his Sears guitar. He started writing his own music right away, with witty lyrics in what would soon become his signature style.

Playing music in rock bands helped Neal work his way through college. Though he earned his degree in psychology from the University of Chicago, he claims to have majored in the Beatles.