Wolfhard and Josh Ovalle co-directed their first music video in July of 2017 for the song of Spendtime Palace, "Sonora". Wolfhard made his film debut as Richie Tozier in the 2017 film adaptation of Stephen King's It. The casting of Wolfhard in both Stranger Things and It, both set in the '80s, had been a coincidence.According to Wolfhard, he had been initially cast as Richie when Cary Fukunaga was attached as director and co-writer, but when Fukunaga left the project over creative differences, the role fell through which allowed him to pursue Stranger Things. Wolfhard was required to re-audition for Richie's role after Andy Muschietti was attached to It. In October 2017, Wolfhard parted ways with his former agency APA and fired his former agent Tyler Grasham following allegations that Grasham had assaulted and sexually assaulted promising young male actors. Wolfhard himself had not been assaulted. In January of 2018, Wolfhard signed with talent agency, CAA. He played Tyler, an altruistic and thoughtful pizza delivery boy in the 2018 Ken Marino-directed ensemble comedy film Dog Days.
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