Career
Jackson started acting in a small role in the film Crooked Hearts in 1991. The next year, he played the role of Charlie in a musical version of Willy 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. Soon after, he landed the role of Charlie (#96) in The Mighty Ducks series, playing a young and aspiring hockey player.
Jackson went on to appear as Pacey Witter on Dawson's Creek, which was created by Kevin Williamson and ran on the WB network from 1998 to 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 (an 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 in which he appears as himself in a poker scene with Brad Pitt, George Clooney and Holly Marie Combs. 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". He also was cast as "Beau" in the movie Gossip in 2000 with actors James Marsden, Kate Hudson and Norman Reedus.
Shortly after Dawson's Creek ended in 2003, Jackson played the lead role in films alongside Dennis Hopper (Americano), Harvey Keitel (Shadows in the Sun), and Donald Sutherland (Aurora Borealis). In 2005, Jackson moved to the UK and made his stage debut on the London West End with Patrick Stewart in David Mamet's two-man play, A Life in the Theatre. 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. His next film role was in Bobby, directed by Emilio Estevez, Jackson's co-star from The Mighty Ducks. He played a lead role in Shutter, a U.S. remake of film of the same name. He starred and acted as executive producer in the Canadian independent film One Week, which opened on March 6, 2009.
From 2008 to 2013, Jackson played the lead role of Peter Bishop in the science-fiction series Fringe, created by J. J. Abrams, Roberto Orci and Alex Kurtzman. The series was the second-highest rated new show of the 2008–2009 season after The Mentalist. BuddyTV ranked him #9 on its "TV's 100 Sexiest Men of 2010" list, #19 in 2011 and #14 in 2012.
Jackson was nominated for a Genie Award for Best Performance by an Actor in a Leading Role for the film One Week. He won the award on April 12, 2010. He held and hosted the satirical Pacey-Con in 2010, directly across the street from the Comic-Con, sporting a bowling shirt and giving out fan fiction, written by Dawson's Creek fans, to those waiting in the Comic-Con entrance line. 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. In 2013, Jackson appeared in the IFC film Inescapable with Marisa Tomei and Alexander Siddig. Jackson wrote the first story from the comic book trilogy Beyond the Fringe, titled "Peter and the Machine". Jackson starred in the successful television show The Affair, where he played Cole Lockhart, the protagonist husband of the unfaithful Alison Lockhart.
In March 2018, Jackson made his theatrical debut on Broadway in Children of a Lesser God, where he played James Leeds, an unconventional teacher at a school for the deaf who gets in a conflicted professional and romantic relationship with a deaf former student, Sarah Norman (Lauren Ridloff). The play ran through May 2018.
In 2019, Jackson starred as defense attorney Mickey Joseph in the miniseries When They See Us.
In 2020, Jackson co-starred with Reese Witherspoon and Kerry Washington in the miniseries Little Fires Everywhere based on the novel by Celeste Ng.
Jackson was cast as Dr. Christopher Duntsch, a neurosurgeon who was convicted of intentionally maiming his patient, in Dr. Death which was based on the podcast of the same name, replacing Jamie Dornan.
In 2023, Jackson played the lead in the series Fatal Attraction with Lizzy Caplan, inspired by the 1980s thriller film of the same name.