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Hill had comedic roles in films including The 40-Year-Old Virgin (2005), Knocked Up (2007), Superbad (2007), Get Him to the Greek (2010), 21 Jump Street (2012), This Is the End (2013), and 22 Jump Street (2014). For his performances in Moneyball (2011) and The Wolf of Wall Street (2013), he was nominated for the Academy Award for Best Supporting Actor. He also had roles in Cyrus (2010), War Dogs (2016), Don't Worry, He Won't Get Far on Foot (2018), and Don't Look Up (2021).

Hill voiced characters in the animated films Horton Hears a Who! (2008), the How to Train Your Dragon franchise (2010–2019), Megamind (2010), The Lego Movie franchise (2014–2019), and Sausage Party (2016). As a screenwriter, he contributed to the stories of 21 Jump Street, 22 Jump Street, Sausage Party, Why Him? (2016), and You People (2023). He starred in the Netflix miniseries Maniac (2018). He made his directorial debut with the film Mid90s (2018), for which he also wrote the screenplay. He directed and produced the documentary Stutz (2022).