Born in Vancouver, British Columbia, on June 11, 1978, Jackson spent most of his early childhood in California with his casting director mother. After moving back to Vancouver, Jackson got his start in commercials, and from there went on to appear in a number of forgettable films. His big break came in 1992 with The Mighty Ducks and its two sequels. Following these, he got a bit role in a film that was helping to usher in the teen horror flick craze, Scream 2 (1997). Then, in 1998, Jackson landed the part that was to give him stardom in Dawson's Creek. As the show gained popularity among both critics and television viewers, Jackson was able to broaden his film experience with 1998's Apt Pupil and Urban Legend. In 1999 he appeared as the gay and peroxided Blaine Tuttle in Cruel Intentions, which he starred in with fellow teen sensations Sarah Michelle Gellar, Ryan Phillippe, and Reese Witherspoon. For his next role, however, Jackson chose to stray from the teen genre with his appearance in Muppets From Space (1999), where his co-stars were more likely to do advertisements for the Children's Broadcasting Network than Noxzema.

In 2000, the young actor returned to the teen genre with two separate projects, The Skulls and Gossip. Both films were set on elite college campuses and featured Jackson as upright young men forced to right the wrongs committed by their peers, something that signified the audience's growing identification with the actor as an unlikely hero for the new millennium.