Soon after he took up acting, Jackson landed the role of Charlie in the The Mighty Ducks series, a part for which Jake Gyllenhaal was also considered (years later both would also be amongst a small group of actors considered for the role of Bruce Wayne/Batman in Batman Begins, which eventually went to Christian Bale). However the role for which Jackson is best known is as the lovable-smart-ass-side-kick Pacey Witter on Dawson’s Creek. This television show, which was one of the most popular on the now defunct WB network, ran from 1998-2003, and also starred James Van Der Beek, Michelle Williams and Katie Holmes. While the show was on hiatus, he appeared in several movies including Cruel Intentions, The Skulls, The Safety of Objects, The Laramie Project and a short cameo in the remake of Ocean’s Eleven where he appears as himself in a poker scene with Brad Pitt, George Clooney and Topher Grace, among others. In 2000, he also guest starred in Season 12 of The Simpsons, voicing the character of Jesse Grass, a “hunky environmentalist” and love interest for Lisa Simpson in the episode Lisa the Tree Hugger.
