Jackson was born in Queens, New York, in 1943 and raised on Long Island, about forty miles from New York City. He first heard rhythm and blues music in 1955, played on the radio by the legendary disc jockey Alan Freed, who described the music as "rock and roll." This led to Jackson's lifelong interest in the music. While teaching public school on Long Island, Jackson wrote his first two books, Big Beat Heat: Alan Freed and the Early Years of Rock and Roll and American Bandstand: Dick Clark and the Making of a Rock and Roll Empire. Each book received the Ralph J. Gleason Music Book Award as well as the Association for Recorded Sound Collections award for Best Research in the field of recorded Rock, Rhythm & Blues, or Soul (1992 & 1998). In 1998, NBC-TV broadcast the movie Mr. Rock and Roll, which was based on Jackson's Alan Freed book.

Jackson became interested in writing about Philly soul music during the time he spent in Philadelphia conducting research for his American Bandstand book. When discussing Philly's early 1960s American Bandstand-driven white "teen idol" recording scene, several people spoke of a local group of young Black singers and writers, among them Kenny Gamble, Leon Huff and Thom Bell. They believed these artists were not able to break into the music business in the early 1960s due to Bandstand's prevailing dominance, coupled with the city's racist attitudes. Jackson thought this would make a good story in itself and in 1998, after retiring from teaching, he began work on A House On Fire: The Rise and Fall of Philadelphia Soul.