While the show was on hiatus, he appeared in several movies including Cruel Intentions (a New York yuppie adaptation of Les Liaisons dangereuses that also starred Sarah Michelle Gellar and Ryan Phillippe), 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 Holly Marie Combs, 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".
Footage of the event was recorded for a video, entitled 'Pacey-Con', which he was filming for Will Ferrell's Funny or Die celebrity humor website.
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He has just finished the second season of the Showtime series The Affair.
Jackson was in a relationship with Dawson's Creek co-star Katie Holmes during the first two seasons of the show's run. He previously lived in Wilmington, North Carolina, where Dawson's Creek was filmed; and in New York, where Fringe filmed its first season.
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The next year, he played the role of Charlie in a musical version of Willie Wonka and the Chocolate Factory.
At this point, with the help of the play's casting director Laura Kennedy, he joined the William Morris Agency.
The play was a critical and popular success, and ran from February to April of that year.
Jackson said that he would consider returning to the stage, to try his hand on Broadway.
Katie’s parents and “friends” are apparently team Josh too.
The mag’s insider claims her parents “have always liked him,” and “friends are convinced they’re more than just old buddies.” It is unclear at this time if the two are actually dating or looking to rekindle any type of romance, but if this is true, we’re wondering what Josh’s ex is thinking?
His next film role was in Bobby, directed by Emilio Estevez, Jackson's co-star from The Mighty Ducks.