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During the 1990s and 2000s, Green began starring in comedy films such as Idle Hands (1999), Rat Race (2001), Without a Paddle (2004), and Be Cool (2005). He also became known for his portrayal of Scott Evil, Dr. Evil's son, in the Austin Powers film series (1997–2002). Green has also taken serious roles in films, including The Attic Expeditions (2001) and Party Monster (2003). He has provided the voice for Howard the Duck in a number of Marvel Cinematic Universe films and series, including Guardians of the Galaxy (2014), Guardians of the Galaxy Vol. 2 (2017), and Guardians of the Galaxy Vol. 3 (2023) and in the animated series What If...? (2021–present). In 2019, he wrote, directed, and starred in the comedy-drama film Changeland.

Green's first lead role on television was on the ABC sitcom Good & Evil in 1991, for which he won a Young Artist Award. Green later gained attention for his supporting roles as Oz, a teenage guitarist and the boyfriend of Willow Rosenberg, on the fantasy television series Buffy the Vampire Slayer (1997–2000), and as the voice of Chris Griffin on the Fox adult animated comedy series Family Guy (1999–present). He also voiced Leonardo in the Nickelodeon animated series Teenage Mutant Ninja Turtles (2014–2017) and the Joker in the Mass Effect video game series (2007–2012). Green created, directed, wrote, and produced the adult animated comedy series Robot Chicken and its spinoffs (2005–present), which have earned him three Primetime Emmy Awards and five Annie Awards.