Jackson's legal studies were undertaken at the Cumberland School of Law at Samford University in Birmingham, Alabama, after which he was admitted to the Tennessee bar.
After this he never faced a truly well-funded or highly organized campaign against him for the next six two-year terms, never failing to receive less than 57% of the vote in any contest despite the district's increasingly Republican nature.
During this period, Jackson established a fairly conservative voting record, generally being pro-business and always anti-abortion, a position at odds with the national Democratic Party but well in tune with a majority of his constituents.
Jackson was elected to a full term in November 2002 by a larger margin over his Republican opponent, retired Humphreys County educator Jim Brasfield, than he had won over Butler two years previously.
Democratic then-Governor Phil Bredesen opposed the "guns bill sponsored by Sen. Doug Jackson, D-Dickson, on the basis that 'guns and alcohol don't mix.'"
Despite Jackson's assertion that, "I haven't gotten a complaint from a single citizen that a permit holder made them feel uncomfortable" there was some public outcry and websites started to voice opposition to the law.