Stroup's first acting role was a guest appearance on a 2005 episode of Unfabulous. Stroup has since appeared in a number of other TV shows, such as Grey's Anatomy, October Road, and True Blood. In 2007, Stroup appeared in 4 episodes of Reaper, in which she played the protagonist's ex-girlfriend. She appeared in a number of small independent movie productions, such as Left in Darkness, Pray for Morning, Vampire Bats.
In March 2007, Stroup starred as the female lead in The Hills Have Eyes 2. Stroup played the role of a US Army National Guardsoldier named Amber who fights for survival with her peers against a group of mutant people. The film was a fast-forward sequel to The Hills Have Eyes, a remake of the 1977 movie of the same name. Despite negative reviews from critics the film went on to gross over $67 million worldwide. That same year Jessica had a supporting role in This Christmas.
In April 2008, Stroup was cast as a series regular on 90210, a reboot of the Golden Globe Award-nominated series Beverly Hills, 90210. Stroup played the role of high school student Erin Silver, the younger sister of David Silver and Kelly Taylor from Beverly Hills, 90210. The pilot premiered on September 2, 2008, to a high 4.65 million viewers despite mixed reviews from critics. In 2010 Stroup was awarded the "Sparkling Performance" award at the Young Hollywood Awards.
Also in April 2008, Stroup played the role of Claire in the film remake Prom Night. In December 2007, MTV.com announced that Stroup was cast in another horror film titled Homecoming, which follows a young woman being kidnapped by her boyfriend's ex-girlfriend. Despite the film completing production in February 2008, it was not released until July 2009 for a limited release in selected cinemas.[5] In 2008, Stroup played Rachel in the ensemble film The Informers.
In 2011, Stroup guest-appeared on Family Guy, in which she voiced a number of characters in two episodes. Stroup reunited with Seth MacFarlane in his directorial debut Ted, in which she played Tracy, a work friend of Lori (played by Mila Kunis).
On August 20, 2013, it was announced that Stroup would join The Following in season 2 as a series regular. Her character, Max, is "the niece of Ryan Hardy (Kevin Bacon). She’s an NYPD cop, currently working in the Intel Division. Max reconnects with Ryan and she becomes a valuable ally."[6]
