He portrayed Norville "Shaggy" Rogers in the live-action movies Scooby-Doo (2002) and Scooby-Doo 2: Monsters Unleashed (2004), and then later voiced the character in several animated releases, serving as the voice of Shaggy since Casey Kasem retired from the role in 2009. Starting in the 2010s, Lillard was more frequently cast in dramatic roles, in films such as The Descendants (2011), Trouble with the Curve (2012), Match (2014), and Twin Peaks: The Return (2017). He also starred in the NBC series Good Girls (2018–2021).
Lillard gained renewed recognition for playing William Afton in the horror film Five Nights at Freddy's (2023); that same year, The Hollywood Reporter praised his return to mainstream popular culture. He has since starred in the fantasy drama film The Life of Chuck (2025).
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