She played a witch disguised as a cheerleader in a 2008 episode of the CW series Supernatural. In films, she was one of the "Six Chicks" in 13 Going on 30, and appeared as Carson in an installment of the Bring It On series, Bring It On: In It to Win It. To land the lead role, she had to terminate her contract with Days of our Lives:
"I got off it, I mean I had talked with the producers about doing this film, and they weren't going to let me do it. I had passed up a lot of other good opportunities this. I really want to do this film. I had just passed up so many opportunities where I could have done a film. So this big thing just came up, and I ended up getting to do this. I'm happier that I got off the soap though. I mean I give all my credit to them, because I have learned so much from being on soap operas and working with amazing actors who've been on there for like thirty, forty years. It was an honor to work with them. It's definitely given me all my background. But getting off the soap opera helped me a lot too, because I can move on to bigger and better things. So I am definitely thankful I got to be on a soap opera though, but yeah..."
She recalled working on a movie set instead of a soap opera set "definitely weird", because she would spend days working on one or two scenes, whereas on the Days of our Lives set, she filmed two or three episodes a day. For Bring It On: In It to Win It, she had to attend cheerleading practice, which was "hard for [her], because [she is] afraid of heights." Nonetheless, she was "glad" to do her own stunts, even though she "wasn't expecting for it to be so hard."
In 2008, she appeared in the Lifetime TV movie Fab Five: The Texas Cheerleader Scandal, where she played head cheerleader Brooke of the Fab Five, which is based on a true story which took place at McKinney North High School in Texas. She "loved" working with her onscreen mother Tatum O'Neal, from who she learned about acting.Furthermore, she was excited to land a supporting role in Bart Got a Room, which aired mainly on film festivals in 2008 before having a limited release in 2009, because it allowed her to work with William H. Macy.
Benson starred in ABC's 2009 television series Eastwick. The show was based on John Updike's novel, The Witches of Eastwick, and the 1987 film adaption of the same name. Her character, Mia, was the teen-aged daughter of Roxie Torcoletti (Rebecca Romijn).
In December 2009, Benson was cast as Hanna Marin in the TV series Pretty Little Liars based on the book series by Sara Shepard.
Benson co starred in Christmas Cupid with Chad Michael Murray and Christina Milian. She recently appeared in One Call's music video for Blacklight. In April of 2011, Benson appeared on an episode of "When I Was 17" airing on MTV. In November 2010 Ashley also made an appearance at the 2010 annual surfer poll awards held in Hawaii with then current boyfriend "Clay Marzo"
