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Darby's international breakthrough came in 2007 with his role as Murray Hewitt in the HBO comedy series "Flight of the Conchords." Since then, he's appeared in films like "Yes Man," "What We Do in the Shadows," and "Jumanji," often injecting his signature comedic flair into supporting roles. On television, he's had recurring roles in shows like "Short Poppies," "Wrecked," and animated shows such as "Voltron: Legendary Defender."

From 2022 to 2023, he starred in period romantic comedy series "Our Flag Means Death" as a fictionalized version of pirate Stede Bonnet. The show was praised for its LGBTQ+ representation, including the romantic relationship between Darby's Bonnet and fellow Kiwi Taika Waititi's Blackbeard. This was not only Darby's first role as a main protagonist, but also his first foray into dramatic acting.

Beyond acting, Darby is also an author. He has written three children's books for his "Buttons McGinty" series as well as an autobiography titled "This Way to Spaceship." Additionally, he's been the host of the cryptozoology podcast "The Cryptid Factor" since 2008, alongside Dan Schreiber, Leon 'Buttons' Kirkbeck, and previously, David Farrier.