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After gaining some recognition in local circles in Jacksonville, Florida and competing at Scribble Jam, Astronautalis self-released his debut album, You and Yer Good Ideas, in 2003. He eventually signed with Fighting Records and the record was re-released in 2005, followed by his second album, The Mighty Ocean and Nine Dark Theaters, in 2006. He released the third album, Pomegranate, on Eyeball Records in 2008. In winter 2009, he toured with the Canadian indie rock band Tegan and Sara through Europe, and supported them again through the spring of 2010 in Australia. His fourth album, This Is Our Science, was released on Fake Four Inc. in 2011. His latest release, Cut the Body Loose, was released in 2016.
Astronautalis has been described as "if Beck were a decade or so younger and had grown up more heavily immersed in hip-hop," with his rapping style noted for "blending styles of indie rock, electro, and talkin' blues" with hip-hop. He has described himself as "historical fiction hip-hop."
During live performances, Astronautalis often performs a freestyle rap based on topics chosen by members of his audience.
You and Yer Good Ideas (self-released, 2003; Fighting, 2005)
The Mighty Ocean & Nine Dark Theaters (Fighting, 2006)