Following a stint working in The Nashville Network’s mailroom, Jackson got his big break when flight attendant Denise met Glen Campbell by chance. The Rhinestone Cowboy then helped to set Jackson on the right track to a deal with Arista Records. That label would release his very first single, “Blue Blooded Woman,” in 1989.
Parent album Here in the Real World was released a year later and spawned his first chart-topping single, “I’d Love You All Over Again.” Jackson’s 1991 follow-up, Don’t Rock the Jukebox, also produced four more number one hits. Then in the fall of 1992, A Lot About Livin’ (And a Little ’bout Love) became Jackson’s first album to top the country charts.
Jackson continued to dominate the country music scene throughout the ’90s, with “Chattahoochee” winning both Song and Single of the Year at the CMAs in 1994. The following year, a successful hits collection was released. By that time, however, he had already bagged membership to the legendary Grand Ole Opry. And success also brought riches: a 100-date U.S. tour in the mid ’90s, for instance, netted him a cool $40 million.