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Root has appeared in numerous Coen brothers films including O Brother, Where Art Thou? (2000), The Ladykillers (2004), No Country for Old Men (2007), The Ballad of Buster Scruggs (2018), and The Tragedy of Macbeth (2021). Other notable film roles include Dave (1993), Bicentennial Man (1999), Dodgeball (2004), Idiocracy (2006), Cedar Rapids (2011), Selma (2014), Trumbo (2015), Get Out (2017), and On the Basis of Sex (2018), as well as his voice roles in Ice Age (2002) and Finding Nemo (2003).

On television, he played supporting roles in Star Trek: The Next Generation (1991), True Blood (2008–2009), Boardwalk Empire (2012–2013), Fargo (2014), The Man in the High Castle (2016–2019), Perry Mason (2020), and Succession (2021–2023). He has received two Primetime Emmy Award nominations for Outstanding Supporting Actor in a Comedy Series, in 2019 for the role of manipulative hitman handler Monroe Fuches in the HBO dark comedy crime series Barry (2018–2023) and in 2026 for the role of fisherman and outspoken superstitious Wyck Crawford in the Apple TV comedy horror series Widow's Bay (2026–present), which he won.