Simmons landed his first feature film role in the 2007 comedy Evan Almighty. He portrayed Dylan Baxter, the oldest of the three sons of Steve Carell's Evan Baxter and Lauren Graham's Joan Baxter. He then starred in a number of films, including the 2009 children's comedy Hotel for Dogs, opposite Jake T. Austin and Emma Roberts. Also in 2009, Simmons starred in the black comedy horror film Jennifer's Body as Chip Dove, the boyfriend of Amanda Seyfried's character, Anita "Needy" Lesnicki. In 2010, he starred in the comedy film Scott Pilgrim vs. the World, portraying Young Neil, a 20-year-old bass guitarist and fan of the fictional band Sex Bob-omb. In 2011, he was cast in a supporting role for the Jonah Hill and Channing Tatum led comedy 21 Jump Street (2012). The film opened at South by Southwest on March 12, and was released theatrically on March 16, 2012.