He starred in New Line Cinema's Horrible Bosses in July 2011, with Jason Bateman, Jason Sudeikis, Kevin Spacey, Jennifer Aniston, Colin Farrell, and Jamie Foxx. He also had a role in the 2010 film Going the Distance, alongside Justin Long, Jason Sudeikis, and Drew Barrymore. In 2013, he voiced the character Art in the Pixar animated film Monsters University and appeared in Guillermo del Toro's film Pacific Rim. In 2017, Day starred in Fist Fight, with Ice Cube. In it, Day plays Andy Campbell, a high school English teacher challenged by his co-worker, history teacher Ronald Strickland (Cube), to a fight after getting him fired. In 2018, he reprised his role for the Pacific Rim sequel, Pacific Rim: Uprising and had a role in Drew Pearce's film Hotel Artemis, with Jodie Foster, Sterling K Brown, Brian Tyree Henry and Jenny Slate.