Jackson’s career exploded throughout the 1990’s, releasing six more albums (including two compilation albums) and 9 chart-topping singles, including "Little Bitty" and "Livin’ on Love". Jackson’s most recent album Good Time was released in March 2008, selling over 119,000 copies in its first week and spawning another chart-topping hit, "Small Town Southern Man".

Of particular note during Jackson’s prolific career are two songs, "It’s Five O’clock Somewhere" and "Where Were You (When the World Stopped Turning)". "It’s Five O’clock Somewhere", a laid-back crossover hit with Jimmy Buffet, was released in 2003 and charted in the top twenty of both the Billboard Hot Country Songs and the Billboard US Hot 100, a mainstream index. "Where Were You (When The World Stopped Turning)" was a song written about the September 11 terrorist attacks, and was originally only played during live sets. The song received so much unsolicited airplay (it proved so popular that radio stations began broadcasting live recordings of it) that Jackson decided to release it as a single in late 2001.